675:
667:
362:
408:
745:
719:
425:), condensation may occur, but this can usually be avoided with mild reagents and low temperatures (e.g., LDA (a strong base), THF, â78 °C). Although the aldol addition usually proceeds to near completion under irreversible conditions, the isolated aldol adducts are sensitive to base-induced retro-aldol cleavage to return starting materials. In contrast, retro-aldol condensations are rare, but possible. This is the basis of the catalytic strategy of class I aldolases in nature, as well as numerous small-molecule amine catalysts.
436:
579:
456:
514:. Kinetic control means that the forward aldol addition reaction must be significantly faster than the reverse retro-aldol reaction. For this approach to succeed, two other conditions must also be satisfied; it must be possible to quantitatively form the enolate of one partner, and the forward aldol reaction must be significantly faster than the transfer of the enolate from one partner to another. Common kinetic control conditions involve the formation of the enolate of a ketone with
1307:
1121:
626:
216:
298:
443:
Thus, if one wishes to obtain only one of the cross-products, one must control which carbonyl becomes the nucleophilic enol/enolate and which remains in its electrophilic carbonyl form. The simplest control is if only one of the reactants has acidic protons, and only this molecule forms the enolate.
420:
Despite the attractiveness of the aldol manifold, there are several problems that need to be addressed to render the process effective. The first problem is a thermodynamic one: most aldol reactions are reversible. Furthermore, the equilibrium is also just barely on the side of the products in the
463:
If one group is considerably more acidic than the other, the most acidic proton is abstracted by the base and an enolate is formed at that carbonyl while the less-acidic carbonyl remains electrophilic. This type of control works only if the difference in acidity is large enough and base is the
1112:
In the usual aldol addition, a carbonyl compound is deprotonated to form the enolate. The enolate is added to an aldehyde or ketone, which forms an alkoxide, which is then protonated on workup. A superior method, in principle, would avoid the requirement for a multistep sequence in favor of a
1103:
However, selectivity requires the slow syringe-pump controlled addition of the desired electrophilic partner because both reacting partners typically have enolizable protons. If one aldehyde has no enolizable protons or alpha- or beta-branching, additional control can be achieved.
834:
If both the enolate and the aldehyde contain pre-existing chirality, then the outcome of the "double stereodifferentiating" aldol reaction may be predicted using a merged stereochemical model that takes into account all the effects discussed above. Several examples are as follows:
1116:
If one coupling partner preferentially enolizes, then the general problem is that the addition generates an alkoxide, which is much more basic than the starting materials. This product binds tightly to the enolizing agent, preventing it from catalyzing additional reactants:
791:
1273:. Following deprotonation of the OH group, isocitrate lyase cleaves isocitrate into the four-carbon succinate and the two-carbon glyoxylate by an aldol cleavage reaction. This cleavage is similar mechanistically to the aldolase A reaction of glycolysis.
822:
1089:
Under Hajos-Parrish conditions only a catalytic amount of proline is necessary (3 mol%). There is no danger of an achiral background reaction because the transient enamine intermediates are much more nucleophilic than their parent ketone enols.
2024:; Dhar, R. K.; Bakshi, R. K.; Pandiarajan, P. K.; Singaram, B. (1989). "Major effect of the leaving group in dialkylboron chlorides and triflates in controlling the stereospecific conversion of ketones into either E- or Z-enol borinates".
891:
Commercial oxazolidinones are relatively expensive, but derive in 2 synthetic steps from comparatively inexpensive amino acids. (Economical large-scale syntheses prepare the auxiliary in-house.) First, a borohydride reduces the acid
877:
357:
salt of the aldol product. The aldol itself is then formed, and it may then undergo dehydration to give the unsaturated carbonyl compound. The scheme shows a simple mechanism for the base-catalyzed aldol reaction of an aldehyde with
1158:
strategies, requiring 8â14 steps, organocatalysis can access many of the same substrates by a two-step protocol involving the proline-catalyzed dimerization of alpha-oxyaldehydes followed by tandem
Mukaiyama aldol cyclization.
1055:
when exposed to ketones. These enamines then react (possibly enantioselectively) with suitable electrophiles. This strategy offers simple enantioselection without transition metals. In contrast to the preference for
953:
869:
2238:; Dart M. J.; Duffy J. L.; Rieger D. L. (1995). "Double Stereodifferentiating Aldol Reactions. The Documentation of "Partially Matched" Aldol Bond Constructions in the Assemblage of Polypropionate Systems".
1169:
The aldol dimerization of alpha-oxyaldehydes requires that the aldol adduct, itself an aldehyde, be inert to further aldol reactions. Earlier studies revealed that aldehydes bearing alpha-alkyloxy or alpha-
237:, a structural motif seen in many of the products. The use of aldehyde in the name comes from its history: aldehydes are more reactive than ketones, so that the reaction was discovered first with them.
1359:
It is typically best to minimize heat for this reaction. As removal of water from excess heat risks shifting the equilibrium in favor of a dehydration reaction, leading to the aldol condensation product.
1219:
2120:; Buse, C. T.; Kleschnick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. (1980). "Acyclic stereoselection. 7. Stereoselective synthesis of 2-alkyl-3-hydroxy carbonyl compounds by aldol condensation".
294:, calcium salt). For many of the commodity applications, the stereochemistry of the aldol reaction is unimportant, but the topic is of intense interest for the synthesis of many specialty chemicals.
1212:
2414:
Crimmins M. T.; King B. W.; Tabet A. E. (1997). "Asymmetric Aldol
Additions with Titanium Enolates of Acyloxazolidinethiones: Dependence of Selectivity on Amine Base and Lewis Acid Stoichiometry".
865:
to create a chiral enolate. The pre-existing chirality from the auxiliary is then transferred to the aldol adduct through
Zimmermann-Traxler methods, and then the oxazolidinone cleaved away.
2088:; Rieger D. L.; Bilodeau M. T.; Urpi F. (1991). "Stereoselective aldol reactions of chlorotitanium enolates. An efficient method for the assemblage of polypropionate-related synthons".
3949:
1163:
1097:
1079:
1000:
973:
1139:
2929:
Garner, Susan Amy (2007) "Hydrogen-mediated carbon-carbon bond formations: Applied to reductive aldol and
Mannich reactions," Ph.D. dissertation, University of Texas (Austin),
932:
900:
885:
839:
396:
by protonation, rendering it highly electrophilic. The enol is nucleophilic at the α-carbon, allowing it to attack the protonated carbonyl compound, leading to the aldol after
381:. In this case, enolate formation is irreversible, and the aldol product is not formed until the metal alkoxide of the aldol product is protonated in a separate workup step.
1093:
A Stork-type strategy also allows the otherwise challenging cross-reactions between two aldehydes. In many cases, the conditions are mild enough to avoid polymerization:
666:
674:
278:
Aldol structural units are found in many important molecules, whether naturally occurring or synthetic. The reaction is used in several industrial syntheses, notably of
6164:
2907:"Chemical notices from foreign sources: Berichte der Deutschen Chemischen Gesellschaft zu Berlin, no. 16, 1869: Valerian aldehyde and Oenanth aldehyde â M. Borodin,"
2174:
Roush W. R. (1991). "Concerning the diastereofacial selectivity of the aldol reactions of .alpha.-methyl chiral aldehydes and lithium and boron propionate enolates".
361:
407:
468:. A typical substrate for this situation is when the deprotonatable position is activated by more than one carbonyl-like group. Common examples include a CH
2267:
Masamune S.; Choy W.; Petersen J. S.; Sita L. R. (1985). "Double
Asymmetric Synthesis and a New Strategy for Stereochemical Control in Organic Synthesis".
2755:; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. (2002). "Diastereoselective Magnesium Halide-Catalyzed anti-Aldol Reactions of Chiral N-Acyloxazolidinones".
2681:
790:
2971:
2548:
Teruaki
Mukaiyama; Kazuo Banno; Koichi Narasaka (1974). "Reactions of silyl enol ethers with carbonyl compounds activated by titanium tetrachloride".
5280:
5225:
5993:
2795:; Downey, C. Wade; Shaw, Jared T.; Tedrow, Jason S. (2002). "Magnesium Halide-Catalyzed Anti-Aldol Reactions of Chiral N-Acylthiazolidinethiones".
2441:
Crimmins M. T.; Chaudhary K. (2000). "Titanium enolates of thiazolidinethione chiral auxiliaries: Versatile tools for asymmetric aldol additions".
738:
988:
approach, a thiazolidinethione is the chiral auxiliary and can produce the "Evans syn" or "non-Evans syn" adducts by simply varying the amount of
5335:
2910:
1526:
5485:
4119:
2951:
2894:
2679:
Eder, Ulrich; Sauer, Gerhard; Wiechert, Rudolf (1971). "New Type of
Asymmetric Cyclization to Optically Active Steroid CD Partial Structures".
2350:; Bartroli J.; Shih T. L. (1981). "Enantioselective aldol condensations. 2. Erythro-selective chiral aldol condensations via boron enolates".
6318:
6214:
2979:
2296:
1456:
160:
5988:
3814:
821:
5090:
3011:
2476:
Crimmins, Michael T.; Shamszad, Mariam (2007). "Highly
Selective Acetate Aldol Additions Using Mesityl-Substituted Chiral Auxiliaries".
5660:
4860:
3604:
567:
group of the aldehyde aligned in a "zig zag" pattern on the paper (or screen). The disposition of the formed stereocenters is deemed
5825:
5755:
5735:
5230:
4397:
3859:
4278:
3834:
2757:
2717:
2550:
2387:
2352:
2240:
2205:
2090:
2058:
2026:
1939:
3047:
2513:
2326:
2324:
Diastereoselective Aldol
Condensation Using A Chiral Oxazolidinone Auxiliary: (2S*,3S*)-3-Hydroxy-3-Phenyl-2-Methylpropanoic Acid
1911:
691:. This "substrate-based stereocontrol" has seen extensive study and examples pervade the literature. In many cases, a stylized
578:
5580:
6058:
6008:
4412:
2203:
Masamune S.; Ellingboe J. W.; Choy W. (1982). "Aldol strategy: coordination of the lithium cation with an alkoxy substituent".
5515:
6154:
5963:
5620:
5600:
5560:
4367:
3310:
2834:"Enantioselective Organocatalytic Direct Aldol Reactions of -Oxyaldehydes: Step One in a Two-Step Synthesis of Carbohydrates"
1892:
1867:
1798:
1738:
1667:
1623:
1554:
1420:
2511:
S. B. Jennifer Kan; Kenneth K.-H. Ng; Ian
Paterson (2013). "The Impact of the Mukaiyama Aldol Reaction in Total Synthesis".
6149:
6079:
5978:
5635:
5490:
5120:
4965:
4575:
4202:
3979:
2650:
Hajos, Zoltan G.; Parrish, David R. (1974). "Asymmetric synthesis of bicyclic intermediates of natural product chemistry".
455:
257:
6229:
6013:
5325:
4815:
4490:
5035:
876:
711:
If the enol has an adjacent stereocenter, then the two stereocenters flanking the carbonyl in the product are naturally
6224:
5938:
5800:
5590:
5555:
2622:
2005:
1361:
By avoiding heat, it can help avoid dehydration so that the majority of product produced is the aldol addition product.
6114:
6053:
5585:
5500:
5470:
5450:
5315:
5310:
4685:
4610:
4253:
4207:
4074:
3335:
2158:
1763:
1590:
896:. Then the resulting amino alcohol dehydratively cyclises with a simple carbonate ester, such as diethylcarbonate.
6219:
6179:
6129:
5805:
5605:
5355:
5285:
3774:
3345:
435:
5420:
4313:
4034:
1487:
757:
5973:
5815:
5685:
5680:
5495:
4970:
4880:
4470:
4402:
4293:
3869:
3624:
3549:
3004:
5730:
6259:
6144:
6043:
5983:
5630:
5425:
5385:
5360:
5270:
4730:
3764:
3694:
3330:
3260:
952:
4850:
319:-butyl propionate). An aldehyde can then be added to the enolate flask to initiate an aldol addition reaction.
6249:
5835:
5725:
5345:
5070:
4855:
4800:
4645:
4605:
4437:
4192:
3909:
3759:
1482:
1451:
1320:
6209:
5770:
5215:
687:
If the two reactants have carbonyls adjacent to a pre-existing stereocenter, then the new stereocenters may
6244:
6159:
6134:
6109:
6094:
6018:
5933:
5830:
5790:
5655:
5610:
5375:
4920:
4905:
4770:
4560:
4228:
3984:
3664:
3639:
3609:
3200:
2652:
2176:
2122:
2056:
Zimmerman, H. E.; Traxler, M. D. (1957). "The Stereochemistry of the Ivanov and Reformatsky Reactions. I".
1340:
868:
421:
case of simple aldehydeâketone aldol reactions. If the conditions are particularly harsh (e.g.: NaOMe/MeOH/
6313:
6308:
6194:
6139:
6084:
5795:
5715:
5615:
5330:
5295:
5140:
5030:
4745:
4740:
4565:
4525:
4422:
4233:
4197:
4049:
4039:
3894:
3754:
3614:
3564:
3559:
3534:
3494:
3440:
3205:
3195:
3170:
2269:
1849:
1325:
481:
378:
369:
Although only a catalytic amount of base is required in some cases, the more usual procedure is to use a
1937:; Nelson J. V.; Vogel E.; Taber T. R. (1981). "Stereoselective aldol condensations via boron enolates".
559:
convention. When propionate (or higher order) nucleophiles add to aldehydes, the reader visualizes the
6169:
5870:
5675:
5110:
4995:
4675:
4650:
4590:
4447:
4182:
3889:
3669:
3634:
3539:
3230:
3165:
2997:
2946:
1239:
1177:
1037:
153:
145:
5460:
3724:
1192:
formation. This requires appropriate diastereocontrol in the Mukaiyama aldol addition and the product
510:
One common solution is to form the enolate of one partner first, and then add the other partner under
400:. Some may also dehydrate past the intended product to give the unsaturated carbonyl compound through
6269:
6174:
6028:
5908:
5880:
5850:
5765:
5695:
5650:
5625:
5545:
5445:
5405:
5100:
4720:
4710:
4635:
4159:
4019:
4014:
3994:
3679:
3476:
3455:
3415:
3340:
2889:
1379:
1231:
545:
To describe relative stereochemistry at the α- and ÎČ-carbon, older papers use saccharide chemistry's
3160:
334:
The aldol reaction has one underlying mechanism, but it appears in different forms depending on pH:
6234:
6124:
6104:
5968:
5810:
5720:
5690:
5670:
5565:
5520:
5350:
5260:
5190:
5075:
5065:
4895:
4452:
4392:
4357:
4164:
4144:
4104:
3879:
3749:
3714:
3674:
3425:
3265:
3255:
3185:
1048:
1021:
700:
530:
into a more complex one. Increased complexity arises because each end of the new bond may become a
515:
511:
473:
374:
325:(â78 °C) the temperature of which is being monitored by a thermocouple (the wire on the left).
304:
5700:
6204:
6063:
5913:
5855:
5780:
5760:
5480:
5430:
5290:
5255:
5195:
5125:
4680:
4427:
4407:
4139:
4059:
3954:
3914:
3884:
3819:
3704:
3689:
3599:
3589:
3250:
3175:
3130:
1188:
product could then be converted to four possible sugars via Mukaiyama aldol addition followed by
637:
477:
268:; on the converse, when the nucleophile and electrophile are the same, the reaction is called an
3465:
1127:
One approach, demonstrated by Evans, is to silylate the aldol adduct. A silicon reagent such as
854:
and coworkers developed a technique for stereoselection in the aldol syntheses of aldehydes and
5943:
5665:
5415:
5395:
5370:
5320:
5235:
5210:
5165:
5135:
5115:
5085:
5050:
5005:
4980:
4955:
4840:
4765:
4545:
4238:
4174:
3974:
3699:
3619:
3305:
3280:
3057:
3052:
1615:
1608:
1281:
The aldol reaction was discovered independently by the Russian chemist (and Romantic composer)
1086:
1041:
539:
245:
2906:
2709:
6279:
5865:
5820:
5535:
5505:
5475:
5410:
5390:
5305:
5300:
5265:
5220:
5205:
5200:
5180:
5170:
5105:
5095:
5025:
4975:
4495:
4298:
3874:
3829:
3659:
3649:
3395:
3320:
3115:
3077:
2934:
1647:
1517:
1478:
1447:
1371:
1286:
641:
487:
Otherwise, the most acidic carbonyls are typically also the most active electrophiles: first
392:
of the carbonyl compound to the enol. The acid also serves to activate the carbonyl group of
350:
202:
3325:
2930:
1780:
6048:
5998:
5948:
5928:
5918:
5775:
5750:
5465:
5455:
5340:
5155:
5150:
5080:
4865:
4665:
4625:
4555:
4520:
4475:
4442:
4308:
4283:
4263:
4084:
4044:
4004:
3969:
3899:
3654:
3524:
3499:
3037:
2385:; Bender S. L.; Morris J. (1988). "The total synthesis of the polyether antibiotic X-206".
1335:
633:
547:
261:
1521:
8:
6254:
6239:
5885:
5860:
5845:
5840:
5570:
5525:
5510:
5400:
5380:
5275:
5160:
5145:
4990:
4935:
4925:
4890:
4655:
4530:
4505:
4417:
4273:
4258:
4243:
4064:
4009:
3779:
3629:
3574:
3445:
3360:
3220:
3145:
2149:
Evans, D. A.; Nelson, J. V.; Taber, T. R. (1982). "Stereoselective Aldol Condensations".
6264:
4915:
4099:
3290:
6003:
5953:
5923:
5785:
5575:
5365:
5250:
5185:
5175:
4940:
4870:
4835:
4830:
4810:
4805:
4750:
4660:
4510:
4372:
4362:
4268:
4054:
3999:
3929:
3849:
3744:
3644:
3579:
3504:
3350:
3215:
3150:
3135:
2831:
2297:"Studies in Asymmetric Synthesis: The Development of Practical Chiral Enolate Synthons"
1659:
1060:
adducts typically observed in enolate-based aldol additions, these aldol additions are
893:
401:
385:
283:
2323:
1908:
1067:
In aqueous solution, the enamine can then be hydrolyzed from the product, making it a
622:
ratio of 80:20 using a lithium enolate compared to 97:3 using a bibutylboron enolate.
5740:
5060:
4945:
4910:
4875:
4820:
4775:
4690:
4670:
4620:
4615:
4585:
4570:
4480:
4387:
4323:
4288:
4114:
3989:
3864:
3789:
3769:
3684:
3519:
3514:
3460:
3370:
3275:
3235:
3190:
3072:
3067:
3032:
2855:
2814:
2774:
2734:
2618:
2580:
2530:
2493:
2458:
2334:
2304:
2154:
2117:
2001:
1888:
1863:
1794:
1759:
1734:
1663:
1639:
1619:
1586:
1550:
1426:
1416:
1387:
1282:
1033:
1016:
A common modification of the aldol reaction uses other, similar functional groups as
587:
535:
465:
429:
271:
249:
186:
182:
37:
4735:
1246:, which is an example of a reverse ("retro") aldol reaction catalyzed by the enzyme
6274:
6119:
6089:
6033:
5958:
5890:
5645:
5595:
5440:
5245:
5020:
5015:
4960:
4950:
4725:
4535:
4515:
4485:
4382:
4318:
4303:
4134:
4089:
4079:
4069:
3964:
3944:
3939:
3924:
3919:
3799:
3794:
3734:
3719:
3709:
3554:
3544:
3410:
3400:
3300:
3295:
3270:
3210:
3062:
3021:
2845:
2806:
2766:
2726:
2690:
2661:
2610:
2576:
2559:
2522:
2485:
2450:
2423:
2396:
2361:
2277:
2249:
2214:
2185:
2131:
2099:
2067:
2035:
2021:
1993:
1948:
1855:
1851:
Stereoselective Synthesis 2: Stereoselective Reactions of Carbonyl and Imino Groups
1828:
1786:
1782:
Stereoselective Synthesis 2: Stereoselective Reactions of Carbonyl and Imino Groups
1711:
1655:
1578:
1496:
1312:
1292:
1258:
1254:
1235:
1218:
1196:
to preferentially cyclize, rather than undergo further aldol reaction. In the end,
1155:
1025:
993:
862:
799:
692:
645:
595:
445:
3390:
2791:
1295:
and Marjorie D. Traxler proposed their model for stereoinduction in a 1957 paper.
752:; in reality, the opposite diastereoface of the aldehyde would have been attacked.
201:) to form a new ÎČ-hydroxy carbonyl compound. Its simplest form might involve the
6184:
5875:
5710:
5705:
5000:
4985:
4930:
4885:
4845:
4795:
4760:
4755:
4700:
4695:
4630:
4580:
4500:
4328:
4212:
4187:
4149:
4124:
4109:
4094:
4029:
3904:
3854:
3844:
3824:
3784:
3594:
3584:
3569:
3365:
3285:
3155:
3125:
3110:
3105:
2797:
2330:
1915:
1549:(6th ed.). Upper Saddle River, New Jersey: Prentice Hall. pp. 1056â66.
1330:
1132:
1068:
943:
855:
688:
503:. Thus cross-aldehyde reactions are typically most challenging because they can
308:
279:
264:. When the nucleophile and electrophile are different, the reaction is called a
253:
20:
2614:
1997:
787:
enolates exhibit anti-Felkin selectivity. The general model is presented below:
6189:
6099:
6038:
5130:
5040:
5010:
4785:
4640:
4377:
4154:
4024:
3839:
3809:
3405:
3180:
3042:
2975:
2792:
2752:
2382:
2347:
2235:
2085:
1934:
1813:
1370:
In this reaction the nucleophile is a boron enolate derived from reaction with
1211:
851:
730:
504:
370:
287:
190:
2989:
2510:
1683:
Paterson, I. (1988). "New Asymmetric Aldol Methodology Using Boron Enolates".
1430:
6302:
6199:
5900:
5745:
5640:
5435:
4825:
4790:
4780:
4715:
4705:
4595:
4432:
4248:
3959:
3934:
3804:
3450:
3435:
3420:
3315:
3245:
3225:
3140:
1859:
1820:
1790:
1500:
1193:
1131:
is added in the reaction, which replaces the metal on the alkoxide, allowing
859:
744:
397:
365:
Simple mechanism for base-catalyzed aldol reaction of an aldehyde with itself
1814:
Guthrie, J.P.; Cooper, K.J.; Cossar, J.; Dawson, B.A.; Taylor, K.F. (1984).
301:
A typical experimental setup for an aldol reaction in a research laboratory.
5240:
4600:
4352:
4129:
3729:
3529:
3380:
3375:
3240:
3095:
2859:
2850:
2833:
2818:
2778:
2738:
2694:
2547:
2534:
2526:
2497:
2462:
2281:
1410:
1383:
939:
780:
531:
449:
322:
291:
241:
2751:
2266:
718:
3739:
3385:
3355:
3120:
2710:"The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes"
2606:
1967:
1920:
1643:
1173:
1120:
996:, analogous to the proposed transition states for the Evans auxiliary.
794:
The general model of the aldol reaction with carbonyl-based stereocontrol
603:
575:, depending if they are on the same or opposite sides of the main chain:
507:
easily or react unselectively to give a statistical mixture of products.
428:
When a mixture of unsymmetrical ketones are reacted, four crossed-aldol (
2665:
2563:
2400:
2365:
2253:
2218:
2189:
2135:
2103:
2071:
2039:
1952:
1575:
March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure
6023:
5550:
4900:
1582:
1270:
1262:
1247:
1243:
1029:
992:. The reaction is believed to proceed via six-membered, titanium-bound
928:
adducts, can be reliably formed using boron-mediated soft enolization:
761:
591:
2832:
Northrup A. B.; Mangion I. K.; Hettche F.; MacMillan D. W. C. (2004).
2810:
2770:
2730:
2489:
2454:
2427:
2234:
2084:
920:
enolate, cannot be obtained reliably with the Evans method. However,
725:
The underlying mechanistic reason depends on the enol isomer. For an
411:
Mechanism for acid-catalyzed aldol reaction of an aldehyde with itself
353:
enolate on the carbonyl group of another molecule. The product is the
1715:
1266:
1230:
Examples of aldol reactions in biochemistry include the splitting of
1185:
1004:
989:
966:
907:
615:
611:
527:
488:
342:
311:(THF). The flask on the left is a solution of the lithium enolate of
1933:
1833:
1815:
1614:. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA. pp.
625:
538:
aldol reactions, but also completely controls both the relative and
3430:
3100:
2881:
2873:
2413:
1170:
1162:
1096:
1078:
389:
354:
346:
338:
194:
124:
73:
58:
2905:
English version of Richter's report: (Staff) (December 10, 1869)
2678:
1642:(1991). "The Aldol Reaction: Acid and General Base Catalysis". In
1289:
in 1872, which originally used aldehydes to perform the reaction.
910:
of an oxazolidinone is informally referred to as "loading done".
244:
in organic chemistry and perhaps the most common means of forming
3090:
2202:
1201:
1197:
1181:
1113:"direct" reaction that could be done in a single process step.
1072:
1052:
999:
811:
607:
492:
206:
2577:
3-Hydroxy-3-Methyl-1-Phenyl-1-Butanone by Crossed Aldol Reaction
972:
825:
Examples of the aldol reaction with carbonyl-based stereocontrol
472:
group flanked by two carbonyls or nitriles (see for example the
1205:
1189:
1151:
1138:
749:
500:
496:
422:
209:
198:
69:
54:
2116:
2055:
931:
899:
884:
838:
518:
at â78 °C, followed by the slow addition of an aldehyde.
297:
215:
2707:
1128:
599:
225:
97:
91:
2892:(V. von Richter from St. Petersburg on 17. October 1869),
2600:
349:, the aldol reaction occurs via nucleophilic attack by the
2440:
2381:
2346:
2020:
1756:
The Art of Writing Reasonable Organic Reaction Mechanisms
1702:
Mestres R. (2004). "A green look at the aldol reaction".
1176:
were suitable for this reaction, while aldehydes bearing
2890:"V. von Richter, aus St. Petersburg am 17. October 1869"
858:. The method works by temporarily appending a chiral
729:
enolate, the stereoinduction is necessary to avoid 1,3-
582:
Syn and anti products from an aldol (addition) reaction
384:
When an acid catalyst is used, the initial step in the
2649:
1075:
efficiently catalyzed the cyclization of a triketone:
748:
For clarity, the stereocenter on the enolate has been
2637:
Z. G. Hajos, D. R. Parrish, German Patent DE 2102623
1107:
586:
The principal factor determining an aldol reaction's
6165:
ErlenmeyerâPlöchl azlactone and amino-acid synthesis
2288:
1302:
1250:(also known as fructose-1,6-bisphosphate aldolase).
979:
2911:
The Chemical News and Journal of Industrial Science
2603:
Catalytic Enantioselective Aldol Addition Reactions
2337:, Coll. Vol. 8, p.339 (1993); Vol. 68, p.83 (1990).
1924:, Coll. Vol. 7, p.185 (1990); Vol. 63, p.89 (1985).
1907:Bal, B.; Buse, C. T.; Smith, K.; Heathcock, C. H.,
1654:. Vol. 2. Elsevier Science. pp. 133â179.
845:
606:
are significantly shorter than other cheap metals (
551:nomenclature; more modern papers use the following
2838:Angewandte Chemie International Edition in English
2682:Angewandte Chemie International Edition in English
1607:
1415:(4th ed.). Hoboken, NJ: Wiley. p. 1014.
5226:Divinylcyclopropane-cycloheptadiene rearrangement
2708:Northrup, Alan B.; MacMillan David W. C. (2002).
1758:(2nd ed.). New York: Springer. p. 133.
880:Four possible stereoisomers of the aldol reaction
534:. Modern methodology has not only developed high-
415:
256:and similar techniques analyze a whole family of
6300:
2230:
2228:
2148:
2051:
2049:
1145:
526:The aldol reaction unites two relatively simple
315:-butyl propionate (formed by addition of LDA to
3019:
2601:Carreira, E. M.; Fettes, A.; Martl, C. (2006).
1990:Asymmetric Aldol Reactions Using Boron Enolates
764:moiety adjacent to the enol will instead cause
689:form at a fixed orientation relative to the old
459:Acidic control of the aldol (addition) reaction
321:Both flasks are submerged in a dry ice/acetone
5486:Thermal rearrangement of aromatic hydrocarbons
4120:Thermal rearrangement of aromatic hydrocarbons
2952:Berichte der deutschen chemischen Gesellschaft
2895:Berichte der deutschen chemischen Gesellschaft
2078:
1987:
1927:
1909:(2SR,3RS)-2,4-Dimethyl-3-Hydroxypentanoic Acid
1854:(1 ed.). Stuttgart: Georg Thieme Verlag.
1785:(1 ed.). Stuttgart: Georg Thieme Verlag.
6215:Lectka enantioselective beta-lactam synthesis
3475:
3005:
2377:
2375:
2225:
2196:
2110:
2046:
1885:Organic synthesis: the disconnection approach
1225:
806:enolates must contain either a destabilizing
5994:Inverse electron-demand DielsâAlder reaction
3815:Heterogeneous metal catalyzed cross-coupling
2949:(On a new derivative of valerian aldehyde),
2434:
2407:
2340:
2260:
1682:
1676:
1632:
1512:
1510:
1473:
1471:
594:. Shorter metal-oxygen bonds "tighten" the
434:
5336:Lobry de BruynâVan Ekenstein transformation
2947:"Ueber einen neuen Abkömmling des Valerals"
2173:
2142:
1882:
1816:"The retroaldol reaction of cinnamaldehyde"
1807:
1728:
1599:
1442:
1440:
1011:
699:, can predict the new orientation from the
682:
3012:
2998:
2372:
2014:
1722:
1701:
1572:
965:A common additional chiral auxiliary is a
5826:Petrenko-Kritschenko piperidone synthesis
5281:FritschâButtenbergâWiechell rearrangement
2849:
2167:
1832:
1753:
1638:
1527:Comptes rendus de l'Académie des sciences
1507:
1468:
5989:Intramolecular DielsâAlder cycloaddition
2986:, Harvard University (pp. 345, 936)
2972:Chem 206, 215 Lecture Notes (2003, 2006)
2872:Borodin reported on the condensation of
2758:Journal of the American Chemical Society
2718:Journal of the American Chemical Society
2551:Journal of the American Chemical Society
2416:Journal of the American Chemical Society
2388:Journal of the American Chemical Society
2353:Journal of the American Chemical Society
2241:Journal of the American Chemical Society
2206:Journal of the American Chemical Society
2091:Journal of the American Chemical Society
2059:Journal of the American Chemical Society
2027:Journal of the American Chemical Society
1940:Journal of the American Chemical Society
1847:
1778:
1605:
1573:Smith, Michael B.; March, Jerry (2006).
1457:Bulletin de la Société Chimique de Paris
1437:
1382:. The thioether is removed in step 2 by
998:
818:-enolates are less diastereoselective:
743:
303:The flask on the right is a solution of
296:
214:
48:
2514:Angewandte Chemie International Edition
1695:
1610:Modern Aldol Reactions, Volumes 1 and 2
1568:
1566:
810:-pentane interaction or an anti-Felkin
6301:
6009:Metal-centered cycloaddition reactions
5661:DebusâRadziszewski imidazole synthesis
3605:BodrouxâChichibabin aldehyde synthesis
2579:Teruaki Mukaiyama and Koichi Narasaka
2316:
1901:
1754:Grossmann, Robert B. (Jan 2002).
1028:add to carbonyls in the presence of a
771:
670:Anti-aldol formation through E-enolate
598:and effects greater stereoselection.
252:. It lends its name to the family of
6155:Diazoalkane 1,3-dipolar cycloaddition
6059:Vinylcyclopropane (5+2) cycloaddition
5964:Diazoalkane 1,3-dipolar cycloaddition
5736:HurdâMori 1,2,3-thiadiazole synthesis
5231:DowdâBeckwith ring-expansion reaction
4398:HurdâMori 1,2,3-thiadiazole synthesis
3474:
3311:LFER solvent coefficients (data page)
2993:
2294:
1992:. Organic Reactions. pp. 1â200.
1733:. Wiley-Interscience. pp. 118â.
1516:
1485:[About an aldehyde alcohol].
1477:
1446:
1409:Klein, David R. (December 22, 2020).
1408:
678:Syn-aldol formation through Z-enolate
6319:Carbon-carbon bond forming reactions
4966:Sharpless asymmetric dihydroxylation
4203:Methoxymethylenetriphenylphosphorane
1988:Cowden, C. J.; Paterson, I. (2004).
1883:Warren, Stuart; Wyatt, Paul (2008).
1563:
1544:
956:Evans' chiral oxazolidinone cleavage
872:Aldol reaction creates stereoisomers
521:
5091:AllenâMillarâTrippett rearrangement
1538:
949:Many methods cleave the auxiliary:
737:enolate instead seeks to avoid 1,3-
618:). The following reaction gives a
13:
6230:Nitrone-olefin (3+2) cycloaddition
6225:Niementowski quinazoline synthesis
6014:Nitrone-olefin (3+2) cycloaddition
5939:Azide-alkyne Huisgen cycloaddition
5801:Niementowski quinazoline synthesis
5556:Azide-alkyne Huisgen cycloaddition
4861:MeerweinâPonndorfâVerley reduction
4413:LeimgruberâBatcho indole synthesis
2965:
1660:10.1016/B978-0-08-052349-1.00027-5
1524:[On an aldehyde alcohol].
1454:[On an aldehyde alcohol].
1285:in 1869 and by the French chemist
1217:
1210:
1161:
1137:
1119:
1095:
1077:
971:
951:
930:
898:
883:
875:
867:
837:
820:
789:
717:
701:configuration of a 6-membered ring
673:
665:
624:
577:
454:
406:
360:
14:
6330:
6054:Trimethylenemethane cycloaddition
5756:JohnsonâCoreyâChaykovsky reaction
5621:CadoganâSundberg indole synthesis
5601:BohlmannâRahtz pyridine synthesis
5561:BaeyerâEmmerling indole synthesis
4368:CadoganâSundberg indole synthesis
3860:JohnsonâCoreyâChaykovsky reaction
1729:Jie Jack Li; et al. (2004).
980:Crimmins thiazolidinethione aldol
439:Crossed aldol (addition) reaction
258:carbonyl α-substitution reactions
6150:CookâHeilbron thiazole synthesis
5979:Hexadehydro DielsâAlder reaction
5806:Niementowski quinoline synthesis
5636:CookâHeilbron thiazole synthesis
5581:BischlerâMöhlau indole synthesis
5491:TiffeneauâDemjanov rearrangement
5121:BakerâVenkataraman rearrangement
4279:HornerâWadsworthâEmmons reaction
3950:Mizoroki-Heck vs. Reductive Heck
3835:HornerâWadsworthâEmmons reaction
3346:Neighbouring group participation
2153:. Vol. 13. pp. 1â115.
1305:
1257:of plants and some prokaryotes,
846:Oxazolidinone chiral auxiliaries
632:Where the counterion determines
373:amount of a strong base such as
5686:Fiesselmann thiophene synthesis
5516:WestphalenâLettrĂ© rearrangement
5496:Vinylcyclopropane rearrangement
5326:KornblumâDeLaMare rearrangement
4971:Epoxidation of allylic alcohols
4881:Noyori asymmetric hydrogenation
4816:KornblumâDeLaMare rearrangement
4491:GallagherâHollander degradation
2939:
2923:
2866:
2825:
2785:
2745:
2701:
2672:
2643:
2631:
2594:
2570:
2541:
2504:
2469:
1981:
1959:
1876:
1841:
1772:
1747:
1652:Comprehensive Organic Synthesis
1364:
1184:were unreactive. The protected
1069:small organic molecule catalyst
432:) products can be anticipated:
6145:Chichibabin pyridine synthesis
5631:Chichibabin pyridine synthesis
5591:BlumâIttah aziridine synthesis
5426:Ring expansion and contraction
3695:Cross dehydrogenative coupling
2888:) in: von Richter, V. (1869)
2609:Vol. 67. pp. 1â216.
1402:
1353:
781:Felkin diastereoface selection
706:
542:of these new stereocenters.
416:Crossed-aldol reactant control
1:
6115:BischlerâNapieralski reaction
6073:Heterocycle forming reactions
5726:Hemetsberger indole synthesis
5586:BischlerâNapieralski reaction
5501:WagnerâMeerwein rearrangement
5471:SommeletâHauser rearrangement
5451:SeyferthâGilbert homologation
5316:IrelandâClaisen rearrangement
5311:HofmannâMartius rearrangement
5071:2,3-sigmatropic rearrangement
4686:CoreyâWinter olefin synthesis
4611:BartonâMcCombie deoxygenation
4254:CoreyâWinter olefin synthesis
4208:SeyferthâGilbert homologation
4075:SeyferthâGilbert homologation
1779:Molander, G. A., ed. (2011).
1488:Journal fĂŒr Praktische Chemie
1483:"Ueber einen Aldehyd-Alkohol"
1396:
1146:Use in carbohydrate synthesis
960:
850:In the late 1970s and 1980s,
444:For example, the addition of
329:
6220:LehmstedtâTanasescu reaction
6180:GabrielâColman rearrangement
6135:Bucherer carbazole synthesis
6130:BorscheâDrechsel cyclization
6110:Bernthsen acridine synthesis
6095:Bamberger triazine synthesis
6080:AlgarâFlynnâOyamada reaction
5791:Nazarov cyclization reaction
5656:De Kimpe aziridine synthesis
5611:Bucherer carbazole synthesis
5606:BorscheâDrechsel cyclization
5376:Nazarov cyclization reaction
5356:MeyerâSchuster rearrangement
5286:GabrielâColman rearrangement
5036:WolffensteinâBöters reaction
4921:Reduction of nitro compounds
4771:Grundmann aldehyde synthesis
4576:AlgarâFlynnâOyamada reaction
3985:Olefin conversion technology
3980:NozakiâHiyamaâKishi reaction
3775:GabrielâColman rearrangement
3665:Claisen-Schmidt condensation
3610:Bouveault aldehyde synthesis
2653:Journal of Organic Chemistry
2177:Journal of Organic Chemistry
2123:Journal of Organic Chemistry
1965:Cowden, C. J.; Paterson, I.
1341:Claisen-Schmidt condensation
1154:use variations of iterative
563:group of the ketone and the
223:These products are known as
7:
6195:Hantzsch pyridine synthesis
5974:Enoneâalkene cycloadditions
5796:Nenitzescu indole synthesis
5716:Hantzsch pyridine synthesis
5681:FerrarioâAckermann reaction
5331:Kowalski ester homologation
5296:Halogen dance rearrangement
5141:Benzilic acid rearrangement
4566:Akabori amino-acid reaction
4526:Von Braun amide degradation
4471:BarbierâWieland degradation
4423:Nenitzescu indole synthesis
4403:KharaschâSosnovsky reaction
4294:JuliaâKocienski olefination
4198:Kowalski ester homologation
3895:Kowalski ester homologation
3870:JuliaâKocienski olefination
3625:CadiotâChodkiewicz coupling
3550:Aza-BaylisâHillman reaction
3495:Acetoacetic ester synthesis
3206:Dynamic binding (chemistry)
3196:Conrotatory and disrotatory
3171:Charge remote fragmentation
2615:10.1002/0471264180.or067.01
2270:Angew. Chem. Int. Ed. Engl.
1998:10.1002/0471264180.or051.01
1731:Contemporary Drug Synthesis
1298:
1178:Electron-withdrawing groups
986:Crimmins thiazolidinethione
758:FrĂĄter & Seebach showed
482:acetoacetic ester synthesis
476:and the first steps of the
452:produces only one product:
341:is a moderate base such as
10:
6335:
6260:RobinsonâGabriel synthesis
6210:Kröhnke pyridine synthesis
6044:Retro-DielsâAlder reaction
5984:Imine DielsâAlder reaction
5771:Kröhnke pyridine synthesis
5386:NewmanâKwart rearrangement
5361:MislowâEvans rearrangement
5271:FischerâHepp rearrangement
5216:Di-Ï-methane rearrangement
4996:Stephen aldehyde synthesis
4731:EschweilerâClarke reaction
4448:Williamson ether synthesis
3765:FujiwaraâMoritani reaction
3670:Combes quinoline synthesis
3635:Carbonyl olefin metathesis
3336:More O'FerrallâJencks plot
3261:GrunwaldâWinstein equation
3231:Electron-withdrawing group
3166:Catalytic resonance theory
1460:. 2nd series (in French).
1276:
1240:glyceraldehyde-3-phosphate
1226:Biological aldol reactions
1038:boron trifluoride etherate
916:adducts, which require an
829:
602:is often used because its
18:
6270:Urech hydantoin synthesis
6250:PomeranzâFritsch reaction
6175:Fischer oxazole synthesis
6072:
5909:1,3-Dipolar cycloaddition
5899:
5881:Urech hydantoin synthesis
5851:Reissert indole synthesis
5836:PomeranzâFritsch reaction
5766:Knorr quinoline synthesis
5696:Fischer oxazole synthesis
5626:Camps quinoline synthesis
5546:1,3-Dipolar cycloaddition
5534:
5446:Semipinacol rearrangement
5421:RambergâBĂ€cklund reaction
5406:Piancatelli rearrangement
5346:McFadyenâStevens reaction
5101:Alpha-ketol rearrangement
5049:
4856:McFadyenâStevens reaction
4801:KilianiâFischer synthesis
4721:Elbs persulfate oxidation
4646:BouveaultâBlanc reduction
4606:BaeyerâVilliger oxidation
4544:
4461:
4438:SchottenâBaumann reaction
4341:
4314:RambergâBĂ€cklund reaction
4221:
4193:KilianiâFischer synthesis
4173:
4035:RambergâBĂ€cklund reaction
4020:Pinacol coupling reaction
4015:Piancatelli rearrangement
3910:LiebeskindâSrogl coupling
3760:FujimotoâBelleau reaction
3483:
3477:List of organic reactions
3341:Negative hyperconjugation
3086:
3028:
2322:Gage J. R.; Evans D. A.,
2151:Topics in Stereochemistry
1380:N,N-diisopropylethylamine
1321:AldolâTishchenko reaction
1232:fructose-1,6-bisphosphate
1150:Traditional syntheses of
167:
141:Organic Chemistry Portal
135:
108:
89:
80:
65:
52:
43:
28:
6245:PictetâSpengler reaction
6160:EinhornâBrunner reaction
6125:Boger pyridine synthesis
6019:Oxo-DielsâAlder reaction
5934:Aza-DielsâAlder reaction
5831:PictetâSpengler reaction
5731:HofmannâLöffler reaction
5721:Hegedus indole synthesis
5691:Fischer indole synthesis
5566:Bartoli indole synthesis
5521:Willgerodt rearrangement
5351:McLafferty rearrangement
5261:Ferrier carbocyclization
5076:2,3-Wittig rearrangement
5066:1,2-Wittig rearrangement
4906:ParikhâDoering oxidation
4896:Oxygen rebound mechanism
4561:AdkinsâPeterson reaction
4453:Yamaguchi esterification
4393:Hegedus indole synthesis
4358:Bartoli indole synthesis
4229:BamfordâStevens reaction
4145:Weinreb ketone synthesis
4105:Stork enamine alkylation
3880:Knoevenagel condensation
3750:Ferrier carbocyclization
3640:CastroâStephens coupling
3266:Hammett acidity function
3256:Free-energy relationship
3201:CurtinâHammett principle
3186:Conformational isomerism
1860:10.1055/sos-sd-202-00331
1791:10.1055/sos-sd-202-00331
1522:"Sur un aldéhyde-alcool"
1501:10.1002/prac.18720050148
1452:"Sur un aldéhyde-alcool"
1346:
1108:"Direct" aldol additions
1085:This combination is the
1071:. In a seminal example,
1051:, secondary amines form
1049:Stork enamine alkylation
1022:Mukaiyama aldol reaction
683:Zimmermann-Traxler model
474:Knoevenagel condensation
388:involves acid-catalyzed
305:lithium diisopropylamide
290:, and the drug Lipitor (
219:Prototype aldol reaction
19:Not to be confused with
6205:Knorr pyrrole synthesis
6140:BuchererâBergs reaction
6085:AllanâRobinson reaction
6064:Wagner-Jauregg reaction
5856:Ring-closing metathesis
5781:Larock indole synthesis
5761:Knorr pyrrole synthesis
5616:BuchererâBergs reaction
5481:Stieglitz rearrangement
5461:SkattebĂžl rearrangement
5431:Ring-closing metathesis
5291:Group transfer reaction
5256:Favorskii rearrangement
5196:Cornforth rearrangement
5126:Bamberger rearrangement
5031:WolffâKishner reduction
4851:MarkĂłâLam deoxygenation
4746:FlemingâTamao oxidation
4741:FischerâTropsch process
4428:Oxymercuration reaction
4408:Knorr pyrrole synthesis
4234:BartonâKellogg reaction
4140:Wagner-Jauregg reaction
4060:Ring-closing metathesis
4050:ReimerâTiemann reaction
4040:RauhutâCurrier reaction
3955:Nef isocyanide reaction
3915:Malonic ester synthesis
3885:Knorr pyrrole synthesis
3820:High dilution principle
3755:FriedelâCrafts reaction
3690:Cross-coupling reaction
3615:BuchererâBergs reaction
3600:Blanc chloromethylation
3590:Blaise ketone synthesis
3565:BaylisâHillman reaction
3560:BartonâKellogg reaction
3535:AllanâRobinson reaction
3441:WoodwardâHoffmann rules
3176:Charge-transfer complex
2583:, Coll. Vol. 8, p.323 (
1887:(2nd ed.). Wiley.
1326:BaylisâHillman reaction
1242:in the fourth stage of
1156:protection-deprotection
1135:of the metal catalyst:
1003:NOTE: the structure of
942:may be obtained by one
697:ZimmermanâTraxler model
590:is the enolizing metal
478:malonic ester synthesis
6170:FeistâBenary synthesis
5944:Bradsher cycloaddition
5914:4+4 Photocycloaddition
5871:SimmonsâSmith reaction
5816:PaternĂČâBĂŒchi reaction
5676:FeistâBenary synthesis
5666:Dieckmann condensation
5416:Pummerer rearrangement
5396:Oxy-Cope rearrangement
5371:Myers allene synthesis
5321:Jacobsen rearrangement
5236:Electrocyclic reaction
5211:Demjanov rearrangement
5166:Buchner ring expansion
5136:Beckmann rearrangement
5116:Aza-Cope rearrangement
5111:ArndtâEistert reaction
5086:Alkyne zipper reaction
5006:Transfer hydrogenation
4981:Sharpless oxyamination
4956:Selenoxide elimination
4841:Lombardo methylenation
4766:Griesbaum coozonolysis
4676:CoreyâItsuno reduction
4651:BoylandâSims oxidation
4591:AngeliâRimini reaction
4239:Boord olefin synthesis
4183:ArndtâEistert reaction
4175:Homologation reactions
3975:Nitro-Mannich reaction
3890:KolbeâSchmitt reaction
3700:Cross-coupling partner
3620:Buchner ring expansion
3540:ArndtâEistert reaction
3306:Kinetic isotope effect
3053:Rearrangement reaction
2851:10.1002/anie.200453716
2695:10.1002/anie.197104961
2527:10.1002/anie.201303914
2475:
2282:10.1002/anie.198500013
1848:Molander, ed. (2011).
1222:
1215:
1166:
1142:
1124:
1100:
1087:Hajos-Parrish reaction
1082:
1042:titanium tetrachloride
1008:
976:
957:
946:of the aldol adduct.
935:
903:
888:
881:
873:
842:
826:
795:
753:
722:
679:
671:
629:
583:
540:absolute configuration
460:
440:
412:
366:
326:
266:crossed aldol reaction
262:diketone condensations
240:The aldol reaction is
220:
6029:PausonâKhand reaction
5866:Sharpless epoxidation
5821:Pechmann condensation
5701:FriedlÀnder synthesis
5651:DavisâBeirut reaction
5506:Wallach rearrangement
5476:Stevens rearrangement
5411:Pinacol rearrangement
5391:Overman rearrangement
5306:Hofmann rearrangement
5301:Hayashi rearrangement
5266:Ferrier rearrangement
5221:Dimroth rearrangement
5206:Curtius rearrangement
5201:Criegee rearrangement
5181:Claisen rearrangement
5171:Carroll rearrangement
5106:Amadori rearrangement
5096:Allylic rearrangement
4976:Sharpless epoxidation
4711:DessâMartin oxidation
4636:BohnâSchmidt reaction
4496:Hofmann rearrangement
4299:Kauffmann olefination
4222:Olefination reactions
4160:WurtzâFittig reaction
3995:PalladiumâNHC complex
3875:Kauffmann olefination
3830:Homologation reaction
3680:CoreyâHouse synthesis
3660:Claisen rearrangement
3456:YukawaâTsuno equation
3416:SwainâLupton equation
3396:Spherical aromaticity
3331:MöbiusâHĂŒckel concept
3116:Aromatic ring current
3078:Substitution reaction
2295:Evans, D. A. (1982).
1606:Mahrwald, R. (2004).
1372:dibutylboron triflate
1287:Charles-Adolphe Wurtz
1221:
1214:
1194:silyloxycarbenium ion
1165:
1141:
1123:
1099:
1081:
1002:
975:
955:
934:
924:enolates, leading to
902:
887:
879:
871:
841:
824:
793:
747:
721:
677:
669:
628:
581:
458:
438:
410:
364:
300:
218:
203:nucleophilic addition
6235:PaalâKnorr synthesis
6105:BartonâZard reaction
6049:Staudinger synthesis
5999:Ketene cycloaddition
5969:DielsâAlder reaction
5949:Cheletropic reaction
5929:Alkyne trimerisation
5811:PaalâKnorr synthesis
5776:Kulinkovich reaction
5751:Jacobsen epoxidation
5671:DielsâAlder reaction
5466:Smiles rearrangement
5456:Sigmatropic reaction
5341:Lossen rearrangement
5191:CoreyâFuchs reaction
5156:Boekelheide reaction
5151:Bergmann degradation
5081:Achmatowicz reaction
4866:Methionine sulfoxide
4666:Clemmensen reduction
4626:Bergmann degradation
4556:Acyloin condensation
4521:Strecker degradation
4476:Bergmann degradation
4443:Ullmann condensation
4309:Peterson olefination
4284:Hydrazone iodination
4264:Elimination reaction
4165:ZinckeâSuhl reaction
4085:Sonogashira coupling
4045:Reformatsky reaction
4005:Peterson olefination
3970:Nierenstein reaction
3900:Kulinkovich reaction
3715:DielsâAlder reaction
3675:CoreyâFuchs reaction
3655:Claisen condensation
3525:Alkyne trimerisation
3500:Acyloin condensation
3466:ÎŁ-bishomoaromaticity
3426:ThorpeâIngold effect
3038:Elimination reaction
1545:Wade, L. G. (2005).
1336:Reformatsky reaction
1007:is missing an N atom
739:diaxial interactions
351:resonance-stabilized
6255:Prilezhaev reaction
6240:Pellizzari reaction
5919:(4+3) cycloaddition
5886:Van Leusen reaction
5861:Robinson annulation
5846:Pschorr cyclization
5841:Prilezhaev reaction
5571:Bergman cyclization
5526:Wolff rearrangement
5511:Weerman degradation
5401:Pericyclic reaction
5381:Neber rearrangement
5276:Fries rearrangement
5161:Brook rearrangement
5146:Bergman cyclization
4991:Staudinger reaction
4936:Rosenmund reduction
4926:Reductive amination
4891:Oppenauer oxidation
4681:CoreyâKim oxidation
4656:Cannizzaro reaction
4531:Weerman degradation
4506:Isosaccharinic acid
4418:Mukaiyama hydration
4274:Hofmann elimination
4259:Dehydrohalogenation
4244:Chugaev elimination
4065:Robinson annulation
4010:Pfitzinger reaction
3780:Gattermann reaction
3725:WulffâDötz reaction
3705:DakinâWest reaction
3630:Carbonyl allylation
3575:Bergman cyclization
3361:Kennedy J. P. Orton
3281:Hammond's postulate
3251:FlippinâLodge angle
3221:Electromeric effect
3146:Beta-silicon effect
3131:BakerâNathan effect
2945:Borodin, A. (1873)
2666:10.1021/jo00925a003
2564:10.1021/ja00831a019
2401:10.1021/ja00216a026
2366:10.1021/ja00398a058
2254:10.1021/ja00140a027
2219:10.1021/ja00384a062
2190:10.1021/jo00013a015
2136:10.1021/jo01294a030
2104:10.1021/ja00003a051
2072:10.1021/ja01565a041
2040:10.1021/ja00191a058
1953:10.1021/ja00401a031
1378:BOTf), the base is
772:On the electrophile
246:carbonâcarbon bonds
6314:Addition reactions
6309:Coupling reactions
6004:McCormack reaction
5954:Conia-ene reaction
5786:Madelung synthesis
5576:Biginelli reaction
5366:Mumm rearrangement
5251:Favorskii reaction
5186:Cope rearrangement
5176:Chan rearrangement
4941:Rubottom oxidation
4871:Miyaura borylation
4836:Lipid peroxidation
4831:Lindgren oxidation
4811:Kornblum oxidation
4806:Kolbe electrolysis
4751:Fukuyama reduction
4661:Carbonyl reduction
4511:Marker degradation
4373:Diazonium compound
4363:Boudouard reaction
4342:Carbon-heteroatom
4269:Grieco elimination
4055:Rieche formylation
4000:Passerini reaction
3930:Meerwein arylation
3850:Hydroxymethylation
3745:Favorskii reaction
3645:Chan rearrangement
3580:Biginelli reaction
3505:Aldol condensation
3351:2-Norbornyl cation
3326:Möbius aromaticity
3321:Markovnikov's rule
3216:Effective molarity
3161:BĂŒrgiâDunitz angle
3151:Bicycloaromaticity
2902: : 552-553.
2329:2012-09-29 at the
1914:2011-06-06 at the
1583:10.1002/0470084960
1223:
1216:
1208:were synthesized:
1167:
1143:
1125:
1101:
1083:
1032:catalyst, such as
1009:
977:
958:
936:
904:
889:
882:
874:
843:
827:
796:
754:
723:
680:
672:
630:
584:
461:
441:
413:
402:aldol condensation
386:reaction mechanism
367:
327:
286:, the plasticizer
284:trimethylolpropane
221:
189:that combines two
92:ÎČ-hydroxy Aldehyde
6296:
6295:
6292:
6291:
6288:
6287:
6280:WohlâAue reaction
5924:6+4 Cycloaddition
5741:Iodolactonization
5061:1,2-rearrangement
5026:WohlâAue reaction
4946:Sabatier reaction
4911:Pinnick oxidation
4876:Mozingo reduction
4821:Leuckart reaction
4776:Haloform reaction
4691:Criegee oxidation
4671:Collins oxidation
4621:Benkeser reaction
4616:Bechamp reduction
4586:Andrussow process
4571:Alcohol oxidation
4481:Edman degradation
4388:Haloform reaction
4337:
4336:
4324:Takai olefination
4289:Julia olefination
4115:Takai olefination
3990:Olefin metathesis
3865:Julia olefination
3790:Grignard reaction
3770:Fukuyama coupling
3685:Coupling reaction
3650:ChanâLam coupling
3520:Alkyne metathesis
3515:Alkane metathesis
3371:Phosphaethynolate
3276:George S. Hammond
3236:Electronic effect
3191:Conjugated system
3073:Stereospecificity
3068:Stereoselectivity
3033:Addition reaction
3022:organic reactions
2959: : 982â985.
2844:(16): 2152â2154.
2811:10.1021/ol025553o
2771:10.1021/ja0119548
2731:10.1021/ja0262378
2725:(24): 6798â6799.
2660:(12): 1615â1621.
2587:); Vol. 65, p.6 (
2581:Organic Syntheses
2558:(24): 7503â7509.
2521:(35): 9097â9108.
2490:10.1021/ol062688b
2455:10.1021/ol9913901
2428:10.1021/ja9716721
2422:(33): 7883â7884.
2335:Organic Syntheses
2305:Aldrichimica Acta
2248:(35): 9073â9074.
2213:(20): 1047â1049.
2184:(13): 4151â4157.
1947:(11): 3099â3111.
1894:978-0-470-71236-8
1869:978-3-13-154121-5
1800:978-3-13-154121-5
1740:978-0-471-21480-9
1669:978-0-08-052349-1
1625:978-3-527-30714-2
1556:978-0-13-236731-8
1547:Organic Chemistry
1422:978-1-119-65959-4
1412:Organic chemistry
1283:Alexander Borodin
1034:boron trifluoride
1026:silyl enol ethers
994:transition states
779:enolates exhibit
760:that a chelating
588:stereoselectivity
522:Stereoselectivity
466:limiting reactant
260:, as well as the
250:organic chemistry
187:organic chemistry
171:
170:
104:
103:
38:Coupling reaction
16:Chemical reaction
6326:
6275:Wenker synthesis
6265:Stollé synthesis
6120:Bobbitt reaction
6090:Auwers synthesis
6034:Povarov reaction
5959:Cyclopropanation
5897:
5896:
5891:Wenker synthesis
5646:Darzens reaction
5596:Bobbitt reaction
5441:Schmidt reaction
5246:Enyne metathesis
5021:Whiting reaction
5016:Wharton reaction
4961:Shapiro reaction
4951:Sarett oxidation
4916:Prévost reaction
4726:Emde degradation
4536:Wohl degradation
4516:Ruff degradation
4486:Emde degradation
4383:Grignard reagent
4319:Shapiro reaction
4304:McMurry reaction
4171:
4170:
4135:Ullmann reaction
4100:Stollé synthesis
4090:Stetter reaction
4080:Shapiro reaction
4070:Sakurai reaction
3965:Negishi coupling
3945:Minisci reaction
3940:Michael reaction
3925:McMurry reaction
3920:Mannich reaction
3800:Hammick reaction
3795:Grignard reagent
3735:Enyne metathesis
3720:Doebner reaction
3710:Darzens reaction
3555:Barbier reaction
3545:Auwers synthesis
3472:
3471:
3446:Woodward's rules
3411:Superaromaticity
3401:Spiroaromaticity
3301:Inductive effect
3296:Hyperconjugation
3271:Hammett equation
3211:Edwards equation
3063:Regioselectivity
3014:
3007:
3000:
2991:
2990:
2960:
2943:
2937:
2927:
2921:
2870:
2864:
2863:
2853:
2829:
2823:
2822:
2805:(7): 1127â1130.
2789:
2783:
2782:
2749:
2743:
2742:
2714:
2705:
2699:
2698:
2689:(7): 1615â1621.
2676:
2670:
2669:
2647:
2641:
2635:
2629:
2628:
2598:
2592:
2574:
2568:
2567:
2545:
2539:
2538:
2508:
2502:
2501:
2473:
2467:
2466:
2438:
2432:
2431:
2411:
2405:
2404:
2395:(8): 2506â2526.
2379:
2370:
2369:
2360:(8): 2127â2129.
2344:
2338:
2320:
2314:
2313:
2301:
2292:
2286:
2285:
2264:
2258:
2257:
2232:
2223:
2222:
2200:
2194:
2193:
2171:
2165:
2164:
2146:
2140:
2139:
2130:(6): 1066â1081.
2118:Heathcock, C. H.
2114:
2108:
2107:
2098:(3): 1047â1049.
2082:
2076:
2075:
2066:(8): 1920â1923.
2053:
2044:
2043:
2034:(9): 3441â3442.
2018:
2012:
2011:
1985:
1979:
1963:
1957:
1956:
1931:
1925:
1905:
1899:
1898:
1880:
1874:
1873:
1845:
1839:
1838:
1836:
1827:(8): 1441â1445.
1811:
1805:
1804:
1776:
1770:
1769:
1751:
1745:
1744:
1726:
1720:
1719:
1716:10.1039/b409143b
1699:
1693:
1692:
1680:
1674:
1673:
1640:Heathcock, C. H.
1636:
1630:
1629:
1613:
1603:
1597:
1596:
1570:
1561:
1560:
1542:
1536:
1535:
1514:
1505:
1504:
1475:
1466:
1465:
1444:
1435:
1434:
1406:
1390:
1368:
1362:
1357:
1315:
1313:Chemistry portal
1310:
1309:
1308:
1293:Howard Zimmerman
1259:isocitrate lyase
1255:glyoxylate cycle
1236:dihydroxyacetone
938:Often, a single
856:carboxylic acids
800:transition state
693:transition state
596:transition state
446:diethyl malonate
394:another molecule
193:compounds (e.g.
163:
148:
98:ÎČ-hydroxy Ketone
84:
50:
49:
26:
25:
6334:
6333:
6329:
6328:
6327:
6325:
6324:
6323:
6299:
6298:
6297:
6284:
6185:Gewald reaction
6068:
5895:
5876:Skraup reaction
5711:Graham reaction
5706:Gewald reaction
5537:
5530:
5052:
5045:
5001:Swern oxidation
4986:Stahl oxidation
4931:Riley oxidation
4886:Omega oxidation
4846:Luche reduction
4796:Jones oxidation
4761:Glycol cleavage
4756:Ganem oxidation
4701:Davis oxidation
4696:Dakin oxidation
4631:Birch reduction
4581:Amide reduction
4547:
4540:
4501:Hooker reaction
4463:
4457:
4345:
4343:
4333:
4329:Wittig reaction
4217:
4213:Wittig reaction
4188:Hooker reaction
4169:
4150:Wittig reaction
4125:Thorpe reaction
4110:Suzuki reaction
4095:Stille reaction
4030:Quelet reaction
3905:Kumada coupling
3855:Ivanov reaction
3845:Hydrovinylation
3825:Hiyama coupling
3785:Glaser coupling
3595:Blaise reaction
3585:Bingel reaction
3570:Benary reaction
3487:
3485:
3479:
3470:
3366:Passive binding
3286:Homoaromaticity
3136:Baldwin's rules
3111:Antiaromaticity
3106:Anomeric effect
3082:
3024:
3018:
2968:
2966:Further reading
2963:
2944:
2940:
2928:
2924:
2878:Valerianaldehyd
2871:
2867:
2830:
2826:
2798:Organic Letters
2793:Evans, David A.
2790:
2786:
2750:
2746:
2712:
2706:
2702:
2677:
2673:
2648:
2644:
2636:
2632:
2625:
2599:
2595:
2575:
2571:
2546:
2542:
2509:
2505:
2474:
2470:
2443:Organic Letters
2439:
2435:
2412:
2408:
2380:
2373:
2345:
2341:
2331:Wayback Machine
2321:
2317:
2299:
2293:
2289:
2265:
2261:
2233:
2226:
2201:
2197:
2172:
2168:
2161:
2147:
2143:
2115:
2111:
2083:
2079:
2054:
2047:
2019:
2015:
2008:
1986:
1982:
1964:
1960:
1932:
1928:
1916:Wayback Machine
1906:
1902:
1895:
1881:
1877:
1870:
1846:
1842:
1834:10.1139/v84-243
1812:
1808:
1801:
1777:
1773:
1766:
1752:
1748:
1741:
1727:
1723:
1710:(12): 583â603.
1704:Green Chemistry
1700:
1696:
1681:
1677:
1670:
1637:
1633:
1626:
1604:
1600:
1593:
1571:
1564:
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1539:
1515:
1508:
1476:
1469:
1445:
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1423:
1407:
1403:
1399:
1394:
1393:
1377:
1369:
1365:
1360:
1358:
1354:
1349:
1331:Ivanov reaction
1311:
1306:
1304:
1301:
1279:
1228:
1148:
1110:
1020:enols. In the
1014:
982:
963:
944:crystallization
848:
832:
774:
709:
685:
640:determines its
634:stereoinduction
524:
512:kinetic control
471:
418:
390:tautomerization
332:
320:
309:tetrahydrofuran
302:
280:pentaerythritol
254:aldol reactions
212:to another:
159:
144:
131:
119:
96:
94:
82:
67:
29:Aldol Addition
24:
21:Aldol reactions
17:
12:
11:
5:
6332:
6322:
6321:
6316:
6311:
6294:
6293:
6290:
6289:
6286:
6285:
6283:
6282:
6277:
6272:
6267:
6262:
6257:
6252:
6247:
6242:
6237:
6232:
6227:
6222:
6217:
6212:
6207:
6202:
6197:
6192:
6190:Hantzsch ester
6187:
6182:
6177:
6172:
6167:
6162:
6157:
6152:
6147:
6142:
6137:
6132:
6127:
6122:
6117:
6112:
6107:
6102:
6100:Banert cascade
6097:
6092:
6087:
6082:
6076:
6074:
6070:
6069:
6067:
6066:
6061:
6056:
6051:
6046:
6041:
6039:Prato reaction
6036:
6031:
6026:
6021:
6016:
6011:
6006:
6001:
5996:
5991:
5986:
5981:
5976:
5971:
5966:
5961:
5956:
5951:
5946:
5941:
5936:
5931:
5926:
5921:
5916:
5911:
5905:
5903:
5894:
5893:
5888:
5883:
5878:
5873:
5868:
5863:
5858:
5853:
5848:
5843:
5838:
5833:
5828:
5823:
5818:
5813:
5808:
5803:
5798:
5793:
5788:
5783:
5778:
5773:
5768:
5763:
5758:
5753:
5748:
5743:
5738:
5733:
5728:
5723:
5718:
5713:
5708:
5703:
5698:
5693:
5688:
5683:
5678:
5673:
5668:
5663:
5658:
5653:
5648:
5643:
5638:
5633:
5628:
5623:
5618:
5613:
5608:
5603:
5598:
5593:
5588:
5583:
5578:
5573:
5568:
5563:
5558:
5553:
5548:
5542:
5540:
5532:
5531:
5529:
5528:
5523:
5518:
5513:
5508:
5503:
5498:
5493:
5488:
5483:
5478:
5473:
5468:
5463:
5458:
5453:
5448:
5443:
5438:
5433:
5428:
5423:
5418:
5413:
5408:
5403:
5398:
5393:
5388:
5383:
5378:
5373:
5368:
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5358:
5353:
5348:
5343:
5338:
5333:
5328:
5323:
5318:
5313:
5308:
5303:
5298:
5293:
5288:
5283:
5278:
5273:
5268:
5263:
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5218:
5213:
5208:
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5198:
5193:
5188:
5183:
5178:
5173:
5168:
5163:
5158:
5153:
5148:
5143:
5138:
5133:
5131:Banert cascade
5128:
5123:
5118:
5113:
5108:
5103:
5098:
5093:
5088:
5083:
5078:
5073:
5068:
5063:
5057:
5055:
5051:Rearrangement
5047:
5046:
5044:
5043:
5041:Zinin reaction
5038:
5033:
5028:
5023:
5018:
5013:
5011:Wacker process
5008:
5003:
4998:
4993:
4988:
4983:
4978:
4973:
4968:
4963:
4958:
4953:
4948:
4943:
4938:
4933:
4928:
4923:
4918:
4913:
4908:
4903:
4898:
4893:
4888:
4883:
4878:
4873:
4868:
4863:
4858:
4853:
4848:
4843:
4838:
4833:
4828:
4823:
4818:
4813:
4808:
4803:
4798:
4793:
4788:
4786:Hydrogenolysis
4783:
4778:
4773:
4768:
4763:
4758:
4753:
4748:
4743:
4738:
4736:Ătard reaction
4733:
4728:
4723:
4718:
4713:
4708:
4703:
4698:
4693:
4688:
4683:
4678:
4673:
4668:
4663:
4658:
4653:
4648:
4643:
4641:Bosch reaction
4638:
4633:
4628:
4623:
4618:
4613:
4608:
4603:
4598:
4593:
4588:
4583:
4578:
4573:
4568:
4563:
4558:
4552:
4550:
4546:Organic redox
4542:
4541:
4539:
4538:
4533:
4528:
4523:
4518:
4513:
4508:
4503:
4498:
4493:
4488:
4483:
4478:
4473:
4467:
4465:
4459:
4458:
4456:
4455:
4450:
4445:
4440:
4435:
4430:
4425:
4420:
4415:
4410:
4405:
4400:
4395:
4390:
4385:
4380:
4378:Esterification
4375:
4370:
4365:
4360:
4355:
4349:
4347:
4339:
4338:
4335:
4334:
4332:
4331:
4326:
4321:
4316:
4311:
4306:
4301:
4296:
4291:
4286:
4281:
4276:
4271:
4266:
4261:
4256:
4251:
4246:
4241:
4236:
4231:
4225:
4223:
4219:
4218:
4216:
4215:
4210:
4205:
4200:
4195:
4190:
4185:
4179:
4177:
4168:
4167:
4162:
4157:
4155:Wurtz reaction
4152:
4147:
4142:
4137:
4132:
4127:
4122:
4117:
4112:
4107:
4102:
4097:
4092:
4087:
4082:
4077:
4072:
4067:
4062:
4057:
4052:
4047:
4042:
4037:
4032:
4027:
4025:Prins reaction
4022:
4017:
4012:
4007:
4002:
3997:
3992:
3987:
3982:
3977:
3972:
3967:
3962:
3957:
3952:
3947:
3942:
3937:
3932:
3927:
3922:
3917:
3912:
3907:
3902:
3897:
3892:
3887:
3882:
3877:
3872:
3867:
3862:
3857:
3852:
3847:
3842:
3840:Hydrocyanation
3837:
3832:
3827:
3822:
3817:
3812:
3810:Henry reaction
3807:
3802:
3797:
3792:
3787:
3782:
3777:
3772:
3767:
3762:
3757:
3752:
3747:
3742:
3737:
3732:
3727:
3722:
3717:
3712:
3707:
3702:
3697:
3692:
3687:
3682:
3677:
3672:
3667:
3662:
3657:
3652:
3647:
3642:
3637:
3632:
3627:
3622:
3617:
3612:
3607:
3602:
3597:
3592:
3587:
3582:
3577:
3572:
3567:
3562:
3557:
3552:
3547:
3542:
3537:
3532:
3527:
3522:
3517:
3512:
3510:Aldol reaction
3507:
3502:
3497:
3491:
3489:
3484:Carbon-carbon
3481:
3480:
3469:
3468:
3463:
3461:Zaitsev's rule
3458:
3453:
3448:
3443:
3438:
3433:
3428:
3423:
3418:
3413:
3408:
3406:Steric effects
3403:
3398:
3393:
3388:
3383:
3378:
3373:
3368:
3363:
3358:
3353:
3348:
3343:
3338:
3333:
3328:
3323:
3318:
3313:
3308:
3303:
3298:
3293:
3288:
3283:
3278:
3273:
3268:
3263:
3258:
3253:
3248:
3243:
3238:
3233:
3228:
3223:
3218:
3213:
3208:
3203:
3198:
3193:
3188:
3183:
3178:
3173:
3168:
3163:
3158:
3153:
3148:
3143:
3138:
3133:
3128:
3123:
3118:
3113:
3108:
3103:
3098:
3093:
3087:
3084:
3083:
3081:
3080:
3075:
3070:
3065:
3060:
3058:Redox reaction
3055:
3050:
3045:
3043:Polymerization
3040:
3035:
3029:
3026:
3025:
3017:
3016:
3009:
3002:
2994:
2988:
2987:
2967:
2964:
2962:
2961:
2938:
2922:
2920:
2919:
2886:Oenanthaldehyd
2865:
2824:
2784:
2765:(3): 392â393.
2744:
2700:
2671:
2642:
2630:
2624:978-0471264187
2623:
2593:
2569:
2540:
2503:
2484:(1): 149â152.
2468:
2449:(6): 775â777.
2433:
2406:
2371:
2339:
2315:
2287:
2259:
2224:
2195:
2166:
2159:
2141:
2109:
2077:
2045:
2013:
2007:978-0471264187
2006:
1980:
1958:
1926:
1900:
1893:
1875:
1868:
1840:
1806:
1799:
1771:
1764:
1746:
1739:
1721:
1694:
1675:
1668:
1631:
1624:
1598:
1591:
1562:
1555:
1537:
1506:
1495:(1): 457â464.
1467:
1436:
1421:
1400:
1398:
1395:
1392:
1391:
1375:
1363:
1351:
1350:
1348:
1345:
1344:
1343:
1338:
1333:
1328:
1323:
1317:
1316:
1300:
1297:
1278:
1275:
1227:
1224:
1147:
1144:
1109:
1106:
1013:
1012:"Masked" enols
1010:
981:
978:
962:
959:
852:David A. Evans
847:
844:
831:
828:
773:
770:
731:allylic strain
708:
705:
684:
681:
638:enolate isomer
636:strength, the
523:
520:
499:, and finally
469:
417:
414:
371:stoichiometric
331:
328:
288:2-ethylhexanol
179:aldol addition
175:aldol reaction
169:
168:
165:
164:
157:
150:
149:
146:aldol-addition
142:
138:
137:
133:
132:
129:
127:
121:
120:
117:
115:
111:
110:
106:
105:
102:
101:
87:
86:
78:
77:
63:
62:
46:
45:
41:
40:
35:
34:Reaction type
31:
30:
15:
9:
6:
4:
3:
2:
6331:
6320:
6317:
6315:
6312:
6310:
6307:
6306:
6304:
6281:
6278:
6276:
6273:
6271:
6268:
6266:
6263:
6261:
6258:
6256:
6253:
6251:
6248:
6246:
6243:
6241:
6238:
6236:
6233:
6231:
6228:
6226:
6223:
6221:
6218:
6216:
6213:
6211:
6208:
6206:
6203:
6201:
6200:Herz reaction
6198:
6196:
6193:
6191:
6188:
6186:
6183:
6181:
6178:
6176:
6173:
6171:
6168:
6166:
6163:
6161:
6158:
6156:
6153:
6151:
6148:
6146:
6143:
6141:
6138:
6136:
6133:
6131:
6128:
6126:
6123:
6121:
6118:
6116:
6113:
6111:
6108:
6106:
6103:
6101:
6098:
6096:
6093:
6091:
6088:
6086:
6083:
6081:
6078:
6077:
6075:
6071:
6065:
6062:
6060:
6057:
6055:
6052:
6050:
6047:
6045:
6042:
6040:
6037:
6035:
6032:
6030:
6027:
6025:
6022:
6020:
6017:
6015:
6012:
6010:
6007:
6005:
6002:
6000:
5997:
5995:
5992:
5990:
5987:
5985:
5982:
5980:
5977:
5975:
5972:
5970:
5967:
5965:
5962:
5960:
5957:
5955:
5952:
5950:
5947:
5945:
5942:
5940:
5937:
5935:
5932:
5930:
5927:
5925:
5922:
5920:
5917:
5915:
5912:
5910:
5907:
5906:
5904:
5902:
5901:Cycloaddition
5898:
5892:
5889:
5887:
5884:
5882:
5879:
5877:
5874:
5872:
5869:
5867:
5864:
5862:
5859:
5857:
5854:
5852:
5849:
5847:
5844:
5842:
5839:
5837:
5834:
5832:
5829:
5827:
5824:
5822:
5819:
5817:
5814:
5812:
5809:
5807:
5804:
5802:
5799:
5797:
5794:
5792:
5789:
5787:
5784:
5782:
5779:
5777:
5774:
5772:
5769:
5767:
5764:
5762:
5759:
5757:
5754:
5752:
5749:
5747:
5746:Isay reaction
5744:
5742:
5739:
5737:
5734:
5732:
5729:
5727:
5724:
5722:
5719:
5717:
5714:
5712:
5709:
5707:
5704:
5702:
5699:
5697:
5694:
5692:
5689:
5687:
5684:
5682:
5679:
5677:
5674:
5672:
5669:
5667:
5664:
5662:
5659:
5657:
5654:
5652:
5649:
5647:
5644:
5642:
5641:Cycloaddition
5639:
5637:
5634:
5632:
5629:
5627:
5624:
5622:
5619:
5617:
5614:
5612:
5609:
5607:
5604:
5602:
5599:
5597:
5594:
5592:
5589:
5587:
5584:
5582:
5579:
5577:
5574:
5572:
5569:
5567:
5564:
5562:
5559:
5557:
5554:
5552:
5549:
5547:
5544:
5543:
5541:
5539:
5536:Ring forming
5533:
5527:
5524:
5522:
5519:
5517:
5514:
5512:
5509:
5507:
5504:
5502:
5499:
5497:
5494:
5492:
5489:
5487:
5484:
5482:
5479:
5477:
5474:
5472:
5469:
5467:
5464:
5462:
5459:
5457:
5454:
5452:
5449:
5447:
5444:
5442:
5439:
5437:
5436:Rupe reaction
5434:
5432:
5429:
5427:
5424:
5422:
5419:
5417:
5414:
5412:
5409:
5407:
5404:
5402:
5399:
5397:
5394:
5392:
5389:
5387:
5384:
5382:
5379:
5377:
5374:
5372:
5369:
5367:
5364:
5362:
5359:
5357:
5354:
5352:
5349:
5347:
5344:
5342:
5339:
5337:
5334:
5332:
5329:
5327:
5324:
5322:
5319:
5317:
5314:
5312:
5309:
5307:
5304:
5302:
5299:
5297:
5294:
5292:
5289:
5287:
5284:
5282:
5279:
5277:
5274:
5272:
5269:
5267:
5264:
5262:
5259:
5257:
5254:
5252:
5249:
5247:
5244:
5242:
5239:
5237:
5234:
5232:
5229:
5227:
5224:
5222:
5219:
5217:
5214:
5212:
5209:
5207:
5204:
5202:
5199:
5197:
5194:
5192:
5189:
5187:
5184:
5182:
5179:
5177:
5174:
5172:
5169:
5167:
5164:
5162:
5159:
5157:
5154:
5152:
5149:
5147:
5144:
5142:
5139:
5137:
5134:
5132:
5129:
5127:
5124:
5122:
5119:
5117:
5114:
5112:
5109:
5107:
5104:
5102:
5099:
5097:
5094:
5092:
5089:
5087:
5084:
5082:
5079:
5077:
5074:
5072:
5069:
5067:
5064:
5062:
5059:
5058:
5056:
5054:
5048:
5042:
5039:
5037:
5034:
5032:
5029:
5027:
5024:
5022:
5019:
5017:
5014:
5012:
5009:
5007:
5004:
5002:
4999:
4997:
4994:
4992:
4989:
4987:
4984:
4982:
4979:
4977:
4974:
4972:
4969:
4967:
4964:
4962:
4959:
4957:
4954:
4952:
4949:
4947:
4944:
4942:
4939:
4937:
4934:
4932:
4929:
4927:
4924:
4922:
4919:
4917:
4914:
4912:
4909:
4907:
4904:
4902:
4899:
4897:
4894:
4892:
4889:
4887:
4884:
4882:
4879:
4877:
4874:
4872:
4869:
4867:
4864:
4862:
4859:
4857:
4854:
4852:
4849:
4847:
4844:
4842:
4839:
4837:
4834:
4832:
4829:
4827:
4826:Ley oxidation
4824:
4822:
4819:
4817:
4814:
4812:
4809:
4807:
4804:
4802:
4799:
4797:
4794:
4792:
4791:Hydroxylation
4789:
4787:
4784:
4782:
4781:Hydrogenation
4779:
4777:
4774:
4772:
4769:
4767:
4764:
4762:
4759:
4757:
4754:
4752:
4749:
4747:
4744:
4742:
4739:
4737:
4734:
4732:
4729:
4727:
4724:
4722:
4719:
4717:
4716:DNA oxidation
4714:
4712:
4709:
4707:
4706:Deoxygenation
4704:
4702:
4699:
4697:
4694:
4692:
4689:
4687:
4684:
4682:
4679:
4677:
4674:
4672:
4669:
4667:
4664:
4662:
4659:
4657:
4654:
4652:
4649:
4647:
4644:
4642:
4639:
4637:
4634:
4632:
4629:
4627:
4624:
4622:
4619:
4617:
4614:
4612:
4609:
4607:
4604:
4602:
4599:
4597:
4596:Aromatization
4594:
4592:
4589:
4587:
4584:
4582:
4579:
4577:
4574:
4572:
4569:
4567:
4564:
4562:
4559:
4557:
4554:
4553:
4551:
4549:
4543:
4537:
4534:
4532:
4529:
4527:
4524:
4522:
4519:
4517:
4514:
4512:
4509:
4507:
4504:
4502:
4499:
4497:
4494:
4492:
4489:
4487:
4484:
4482:
4479:
4477:
4474:
4472:
4469:
4468:
4466:
4460:
4454:
4451:
4449:
4446:
4444:
4441:
4439:
4436:
4434:
4433:Reed reaction
4431:
4429:
4426:
4424:
4421:
4419:
4416:
4414:
4411:
4409:
4406:
4404:
4401:
4399:
4396:
4394:
4391:
4389:
4386:
4384:
4381:
4379:
4376:
4374:
4371:
4369:
4366:
4364:
4361:
4359:
4356:
4354:
4351:
4350:
4348:
4344:bond forming
4340:
4330:
4327:
4325:
4322:
4320:
4317:
4315:
4312:
4310:
4307:
4305:
4302:
4300:
4297:
4295:
4292:
4290:
4287:
4285:
4282:
4280:
4277:
4275:
4272:
4270:
4267:
4265:
4262:
4260:
4257:
4255:
4252:
4250:
4249:Cope reaction
4247:
4245:
4242:
4240:
4237:
4235:
4232:
4230:
4227:
4226:
4224:
4220:
4214:
4211:
4209:
4206:
4204:
4201:
4199:
4196:
4194:
4191:
4189:
4186:
4184:
4181:
4180:
4178:
4176:
4172:
4166:
4163:
4161:
4158:
4156:
4153:
4151:
4148:
4146:
4143:
4141:
4138:
4136:
4133:
4131:
4128:
4126:
4123:
4121:
4118:
4116:
4113:
4111:
4108:
4106:
4103:
4101:
4098:
4096:
4093:
4091:
4088:
4086:
4083:
4081:
4078:
4076:
4073:
4071:
4068:
4066:
4063:
4061:
4058:
4056:
4053:
4051:
4048:
4046:
4043:
4041:
4038:
4036:
4033:
4031:
4028:
4026:
4023:
4021:
4018:
4016:
4013:
4011:
4008:
4006:
4003:
4001:
3998:
3996:
3993:
3991:
3988:
3986:
3983:
3981:
3978:
3976:
3973:
3971:
3968:
3966:
3963:
3961:
3960:Nef synthesis
3958:
3956:
3953:
3951:
3948:
3946:
3943:
3941:
3938:
3936:
3935:Methylenation
3933:
3931:
3928:
3926:
3923:
3921:
3918:
3916:
3913:
3911:
3908:
3906:
3903:
3901:
3898:
3896:
3893:
3891:
3888:
3886:
3883:
3881:
3878:
3876:
3873:
3871:
3868:
3866:
3863:
3861:
3858:
3856:
3853:
3851:
3848:
3846:
3843:
3841:
3838:
3836:
3833:
3831:
3828:
3826:
3823:
3821:
3818:
3816:
3813:
3811:
3808:
3806:
3805:Heck reaction
3803:
3801:
3798:
3796:
3793:
3791:
3788:
3786:
3783:
3781:
3778:
3776:
3773:
3771:
3768:
3766:
3763:
3761:
3758:
3756:
3753:
3751:
3748:
3746:
3743:
3741:
3738:
3736:
3733:
3731:
3728:
3726:
3723:
3721:
3718:
3716:
3713:
3711:
3708:
3706:
3703:
3701:
3698:
3696:
3693:
3691:
3688:
3686:
3683:
3681:
3678:
3676:
3673:
3671:
3668:
3666:
3663:
3661:
3658:
3656:
3653:
3651:
3648:
3646:
3643:
3641:
3638:
3636:
3633:
3631:
3628:
3626:
3623:
3621:
3618:
3616:
3613:
3611:
3608:
3606:
3603:
3601:
3598:
3596:
3593:
3591:
3588:
3586:
3583:
3581:
3578:
3576:
3573:
3571:
3568:
3566:
3563:
3561:
3558:
3556:
3553:
3551:
3548:
3546:
3543:
3541:
3538:
3536:
3533:
3531:
3528:
3526:
3523:
3521:
3518:
3516:
3513:
3511:
3508:
3506:
3503:
3501:
3498:
3496:
3493:
3492:
3490:
3486:bond forming
3482:
3478:
3473:
3467:
3464:
3462:
3459:
3457:
3454:
3452:
3451:Y-aromaticity
3449:
3447:
3444:
3442:
3439:
3437:
3436:Walsh diagram
3434:
3432:
3429:
3427:
3424:
3422:
3421:Taft equation
3419:
3417:
3414:
3412:
3409:
3407:
3404:
3402:
3399:
3397:
3394:
3392:
3391:ÎŁ-aromaticity
3389:
3387:
3384:
3382:
3379:
3377:
3374:
3372:
3369:
3367:
3364:
3362:
3359:
3357:
3354:
3352:
3349:
3347:
3344:
3342:
3339:
3337:
3334:
3332:
3329:
3327:
3324:
3322:
3319:
3317:
3316:Marcus theory
3314:
3312:
3309:
3307:
3304:
3302:
3299:
3297:
3294:
3292:
3291:HĂŒckel's rule
3289:
3287:
3284:
3282:
3279:
3277:
3274:
3272:
3269:
3267:
3264:
3262:
3259:
3257:
3254:
3252:
3249:
3247:
3246:Evelyn effect
3244:
3242:
3239:
3237:
3234:
3232:
3229:
3227:
3226:Electron-rich
3224:
3222:
3219:
3217:
3214:
3212:
3209:
3207:
3204:
3202:
3199:
3197:
3194:
3192:
3189:
3187:
3184:
3182:
3179:
3177:
3174:
3172:
3169:
3167:
3164:
3162:
3159:
3157:
3154:
3152:
3149:
3147:
3144:
3142:
3141:Bema Hapothle
3139:
3137:
3134:
3132:
3129:
3127:
3124:
3122:
3119:
3117:
3114:
3112:
3109:
3107:
3104:
3102:
3099:
3097:
3094:
3092:
3089:
3088:
3085:
3079:
3076:
3074:
3071:
3069:
3066:
3064:
3061:
3059:
3056:
3054:
3051:
3049:
3046:
3044:
3041:
3039:
3036:
3034:
3031:
3030:
3027:
3023:
3015:
3010:
3008:
3003:
3001:
2996:
2995:
2992:
2985:
2981:
2977:
2973:
2970:
2969:
2958:
2955:(in German),
2954:
2953:
2948:
2942:
2936:
2932:
2926:
2918: : 286.
2917:
2913:
2912:
2908:
2904:
2903:
2901:
2898:(in German),
2897:
2896:
2891:
2887:
2883:
2879:
2875:
2869:
2861:
2857:
2852:
2847:
2843:
2839:
2835:
2828:
2820:
2816:
2812:
2808:
2804:
2800:
2799:
2794:
2788:
2780:
2776:
2772:
2768:
2764:
2760:
2759:
2754:
2748:
2740:
2736:
2732:
2728:
2724:
2720:
2719:
2711:
2704:
2696:
2692:
2688:
2684:
2683:
2675:
2667:
2663:
2659:
2655:
2654:
2646:
2640:
2634:
2626:
2620:
2616:
2612:
2608:
2604:
2597:
2590:
2586:
2582:
2578:
2573:
2565:
2561:
2557:
2553:
2552:
2544:
2536:
2532:
2528:
2524:
2520:
2516:
2515:
2507:
2499:
2495:
2491:
2487:
2483:
2479:
2472:
2464:
2460:
2456:
2452:
2448:
2444:
2437:
2429:
2425:
2421:
2417:
2410:
2402:
2398:
2394:
2390:
2389:
2384:
2378:
2376:
2367:
2363:
2359:
2355:
2354:
2349:
2343:
2336:
2332:
2328:
2325:
2319:
2311:
2307:
2306:
2298:
2291:
2283:
2279:
2275:
2272:
2271:
2263:
2255:
2251:
2247:
2243:
2242:
2237:
2231:
2229:
2220:
2216:
2212:
2208:
2207:
2199:
2191:
2187:
2183:
2179:
2178:
2170:
2162:
2160:9780471056805
2156:
2152:
2145:
2137:
2133:
2129:
2125:
2124:
2119:
2113:
2105:
2101:
2097:
2093:
2092:
2087:
2081:
2073:
2069:
2065:
2061:
2060:
2052:
2050:
2041:
2037:
2033:
2029:
2028:
2023:
2017:
2009:
2003:
1999:
1995:
1991:
1984:
1977:
1973:
1970:
1969:
1962:
1954:
1950:
1946:
1942:
1941:
1936:
1930:
1923:
1922:
1917:
1913:
1910:
1904:
1896:
1890:
1886:
1879:
1871:
1865:
1861:
1857:
1853:
1852:
1844:
1835:
1830:
1826:
1823:
1822:
1821:Can. J. Chem.
1817:
1810:
1802:
1796:
1792:
1788:
1784:
1783:
1775:
1767:
1765:0-387-95468-6
1761:
1757:
1750:
1742:
1736:
1732:
1725:
1717:
1713:
1709:
1705:
1698:
1690:
1686:
1679:
1671:
1665:
1661:
1657:
1653:
1649:
1645:
1641:
1635:
1627:
1621:
1617:
1612:
1611:
1602:
1594:
1592:9780470084960
1588:
1584:
1580:
1576:
1569:
1567:
1558:
1552:
1548:
1541:
1533:
1530:(in French).
1529:
1528:
1523:
1519:
1513:
1511:
1502:
1498:
1494:
1491:(in German).
1490:
1489:
1484:
1480:
1474:
1472:
1463:
1459:
1458:
1453:
1449:
1443:
1441:
1432:
1428:
1424:
1418:
1414:
1413:
1405:
1401:
1389:
1385:
1381:
1373:
1367:
1356:
1352:
1342:
1339:
1337:
1334:
1332:
1329:
1327:
1324:
1322:
1319:
1318:
1314:
1303:
1296:
1294:
1290:
1288:
1284:
1274:
1272:
1268:
1264:
1260:
1256:
1251:
1249:
1245:
1241:
1237:
1233:
1220:
1213:
1209:
1207:
1203:
1199:
1195:
1191:
1187:
1183:
1179:
1175:
1172:
1164:
1160:
1157:
1153:
1140:
1136:
1134:
1130:
1122:
1118:
1114:
1105:
1098:
1094:
1091:
1088:
1080:
1076:
1074:
1070:
1065:
1064:-selective.
1063:
1059:
1054:
1050:
1045:
1043:
1039:
1035:
1031:
1027:
1023:
1019:
1006:
1001:
997:
995:
991:
990:(â)-sparteine
987:
974:
970:
968:
954:
950:
947:
945:
941:
933:
929:
927:
923:
919:
915:
911:
909:
901:
897:
895:
886:
878:
870:
866:
864:
861:
860:oxazolidinone
857:
853:
840:
836:
823:
819:
817:
813:
809:
805:
801:
792:
788:
786:
782:
778:
769:
767:
763:
759:
751:
746:
742:
740:
736:
732:
728:
720:
716:
714:
704:
702:
698:
695:, called the
694:
690:
676:
668:
664:
662:
658:
655:products and
654:
650:
648:
643:
639:
635:
627:
623:
621:
617:
613:
609:
605:
601:
597:
593:
589:
580:
576:
574:
570:
566:
562:
558:
554:
550:
549:
548:erythro/threo
543:
541:
537:
533:
529:
519:
517:
513:
508:
506:
502:
498:
494:
490:
485:
483:
479:
475:
467:
457:
453:
451:
447:
437:
433:
431:
426:
424:
409:
405:
403:
399:
398:deprotonation
395:
391:
387:
382:
380:
376:
372:
363:
359:
356:
352:
348:
344:
340:
335:
324:
318:
314:
310:
306:
299:
295:
293:
289:
285:
281:
276:
274:
273:
267:
263:
259:
255:
251:
247:
243:
238:
236:
233:ehyde + alcoh
232:
228:
227:
217:
213:
211:
208:
204:
200:
196:
192:
188:
184:
180:
176:
166:
162:
158:
155:
152:
151:
147:
143:
140:
139:
134:
128:
126:
123:
122:
116:
113:
112:
107:
100:
99:
93:
88:
85:
79:
76:
75:
71:
64:
61:
60:
56:
51:
47:
42:
39:
36:
33:
32:
27:
22:
5241:Ene reaction
4601:Autoxidation
4462:Degradation
4353:Azo coupling
4130:Ugi reaction
3730:Ene reaction
3530:Alkynylation
3509:
3381:Polyfluorene
3376:Polar effect
3241:Electrophile
3156:Bredt's rule
3126:Baird's rule
3096:Alpha effect
2983:
2956:
2950:
2941:
2925:
2915:
2909:
2899:
2893:
2885:
2877:
2868:
2841:
2837:
2827:
2802:
2796:
2787:
2762:
2756:
2753:Evans, D. A.
2747:
2722:
2716:
2703:
2686:
2680:
2674:
2657:
2651:
2645:
2638:
2633:
2602:
2596:
2588:
2584:
2572:
2555:
2549:
2543:
2518:
2512:
2506:
2481:
2477:
2471:
2446:
2442:
2436:
2419:
2415:
2409:
2392:
2386:
2383:Evans, D. A.
2357:
2351:
2348:Evans, D. A.
2342:
2318:
2309:
2303:
2290:
2273:
2268:
2262:
2245:
2239:
2236:Evans, D. A.
2210:
2204:
2198:
2181:
2175:
2169:
2150:
2144:
2127:
2121:
2112:
2095:
2089:
2086:Evans, D. A.
2080:
2063:
2057:
2031:
2025:
2022:Brown, H. C.
2016:
1989:
1983:
1975:
1971:
1966:
1961:
1944:
1938:
1935:Evans, D. A.
1929:
1919:
1903:
1884:
1878:
1850:
1843:
1824:
1819:
1809:
1781:
1774:
1755:
1749:
1730:
1724:
1707:
1703:
1697:
1688:
1684:
1678:
1651:
1644:Trost, B. M.
1634:
1609:
1601:
1574:
1546:
1540:
1531:
1525:
1518:Wurtz, C. A.
1492:
1486:
1479:Wurtz, C. A.
1461:
1455:
1448:Wurtz, C. A.
1411:
1404:
1384:Raney Nickel
1366:
1355:
1291:
1280:
1252:
1229:
1174:substituents
1168:
1149:
1126:
1115:
1111:
1102:
1092:
1084:
1066:
1061:
1057:
1046:
1017:
1015:
985:
983:
964:
948:
940:diastereomer
937:
925:
921:
917:
913:
912:
905:
890:
849:
833:
815:
807:
803:
797:
784:
776:
775:
765:
755:
734:
726:
724:
712:
710:
696:
686:
660:
656:
652:
646:
631:
619:
604:bond lengths
585:
572:
568:
564:
560:
556:
552:
546:
544:
532:stereocenter
525:
509:
486:
462:
450:benzaldehyde
442:
427:
419:
393:
383:
368:
336:
333:
323:cooling bath
316:
312:
292:atorvastatin
277:
272:dimerization
269:
265:
242:paradigmatic
239:
234:
230:
224:
222:
178:
174:
172:
161:RXNO:0000016
156:ontology ID
136:Identifiers
114:Temperature
90:
81:
68:
53:
3740:Ethenolysis
3386:Ring strain
3356:Nucleophile
3181:Clar's rule
3121:Aromaticity
2980:A. G. Myers
2976:D. A. Evans
2607:Org. React.
1968:Org. React.
1921:Org. Synth.
1648:Fleming, I.
1386:/ hydrogen
762:Lewis basic
707:On the enol
229:, from the
109:Conditions
6303:Categories
6024:Ozonolysis
5551:Annulation
4901:Ozonolysis
3020:Topics in
1691:: 390â394.
1464:: 436â442.
1431:1201694230
1397:References
1271:isocitrate
1263:glyoxylate
1248:aldolase A
1244:glycolysis
1030:Lewis acid
961:Variations
798:Since the
768:addition.
750:epimerized
733:, while a
592:counterion
505:polymerize
345:ion or an
330:Mechanisms
118:-Î, ~-70°C
5538:reactions
5053:reactions
4548:reactions
4464:reactions
4346:reactions
3488:reactions
2478:Org. Lett
1685:Chem. Ind
1388:reduction
1267:succinate
1261:produces
1186:erythrose
1005:sparteine
967:thioether
908:acylation
863:auxiliary
756:However,
642:direction
616:magnesium
612:aluminium
528:molecules
489:aldehydes
343:hydroxide
307:(LDA) in
195:aldehydes
44:Reaction
3431:Vinylogy
3101:Annulene
3048:Reagents
2882:heptanal
2874:pentanal
2860:15083470
2819:11922799
2779:11792206
2739:12059180
2535:23893491
2498:17192107
2463:10754681
2327:Archived
2276:: 1â30.
1912:Archived
1650:(eds.).
1520:(1872).
1481:(1872).
1450:(1872).
1299:See also
1180:such as
1171:silyloxy
1133:turnover
1053:enamines
783:, while
620:syn:anti
536:yielding
430:addition
355:alkoxide
347:alkoxide
339:catalyst
207:enolized
191:carbonyl
183:reaction
125:Catalyst
74:Aldehyde
59:Aldehyde
3091:A value
2880:) with
1616:1218â23
1534:: 1361.
1277:History
1253:In the
1202:mannose
1198:glucose
1182:acetoxy
1152:hexoses
1073:proline
1047:In the
984:In the
969:group:
830:On both
812:rotamer
649:isomers
608:lithium
495:, then
493:ketones
491:, then
358:itself.
337:If the
199:ketones
181:) is a
130:OH or H
2984:et al.
2858:
2817:
2777:
2737:
2621:
2533:
2496:
2461:
2157:
2004:
1891:
1866:
1797:
1762:
1737:
1666:
1622:
1589:
1553:
1429:
1419:
1206:allose
1204:, and
1190:lactol
1018:ersatz
894:moiety
501:amides
497:esters
423:reflux
379:NaHMDS
270:aldol
226:aldols
210:ketone
205:of an
70:Ketone
55:Ketone
2931:pp. 4
2713:(PDF)
2312:: 23.
2300:(PDF)
1347:Notes
1269:from
1234:into
1129:TMSCl
1040:) or
659:give
651:give
614:, or
600:Boron
484:).
448:into
2933:and
2856:PMID
2815:PMID
2775:PMID
2735:PMID
2639:1971
2619:ISBN
2589:1987
2585:1993
2531:PMID
2494:PMID
2459:PMID
2155:ISBN
2002:ISBN
1978:, 1.
1972:1997
1889:ISBN
1864:ISBN
1795:ISBN
1760:ISBN
1735:ISBN
1664:ISBN
1620:ISBN
1587:ISBN
1551:ISBN
1427:OCLC
1417:ISBN
1374:(nBu
1265:and
1238:and
1062:anti
1036:(as
914:Anti
906:The
802:for
766:anti
703:.
653:anti
573:anti
557:anti
480:and
317:tert
313:tert
173:The
2974:by
2935:51.
2846:doi
2807:doi
2767:doi
2763:124
2727:doi
2723:124
2691:doi
2662:doi
2611:doi
2560:doi
2523:doi
2486:doi
2451:doi
2424:doi
2420:119
2397:doi
2393:110
2362:doi
2358:103
2278:doi
2250:doi
2246:117
2215:doi
2211:104
2186:doi
2132:doi
2100:doi
2096:113
2068:doi
2036:doi
2032:111
1994:doi
1949:doi
1945:103
1856:doi
1829:doi
1787:doi
1712:doi
1656:doi
1579:doi
1497:doi
1058:syn
1044:.
926:syn
808:syn
713:syn
661:syn
644:.
571:or
569:syn
553:syn
516:LDA
377:or
375:LDA
248:in
231:ald
197:or
185:in
154:RSC
72:or
57:or
6305::
2982:,
2978:,
2916:20
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