42:
680:, making it very difficult to work with at large scales. The difficulties encountered during their total synthesis prompted Mukaiyama to pursue an alternative method, and in 2001 a room-temperature oxidation involving N-chlorosuccinimide and a catalytic amount of N-t-butylbenzenesulfenamide was developed. The more
718:
Mukaiyama has been recognized for his achievements in the form of seven honorary degrees and membership in the national academies of four nations. He is the namesake of the
Mukaiyama Award, awarded by the Society of Synthetic Organic Chemistry, Japan since 2005. His major awards include:
310:
reaction β this would become a primary research focus for
Mukaiyama for much of his career. In the original reaction, the phosphine served as the reducing agent by accepting oxygen, while the mercury(II) was the oxidation agent that accepted hydrogens, resulting in the condensation of
465:
A Lewis acid must be added to use silyl enol ethers but not boron enolates because boron has an empty orbital but silicon does not, allowing boron to act as an electron acceptor. Tin(II) goes a step further by having multiple empty orbitals, allowing it to coordinate
462:) and an aldehyde of choice in the presence of a Lewis acid like titanium(IV) chloride. The reaction is a landmark case on how activating aldehydes can allow even electronically neutral and weakly nucleophilic compounds like silyl enol ethers to be used as reagents.
326:, but the most significant was the synthesis of phosphoric esters using DEAD and an alcohol in 1967. The same year that paper was published, Mukaiyama's co-author and former student Oyo Mitsunobu attacked the products of the reaction with a
438:
published a year later and cited both
Mukaiyama and the group of Tyrlik in Poland in his paper, but Japan's position in the international organic chemistry community was not yet fully developed and the naming persists.
688:
increased the stability of the intermediate relative to that formed from the sulfur-carbon bond of DMSO and was inspired by his earlier work with sulfenamides while still at the Tokyo
Institute of Technology.
1415:
Mukaiyama, T.; Matsuo, J.; Iida, D.; Kitagawa, H. (2001). "Catalytic
Oxidation of Various Alcohols to the Corresponding Carbonyl Compounds with N-Chlorosuccinimide Using a Catalytic Amount of Sulfenamide".
703:, citing a belief that "the results of one's chemistry should be published in journals of one's country." The combination of the high quality of his work and the over 600 papers that he published in
358:
compounds which join, forming a carbon-carbon bond. Depending on whether it is performed in acidic or basic conditions, the reaction proceeds by one of the carbonyls attacking the other, which has
697:
Mukaiyama had a scientific career spanning over sixty years, during which he published over 900 papers. After its founding in 1972, Mukaiyama only published in the
Japanese journal
407:
290:
in 1958 and earned his full professorship in 1963. During this time, his main focus was on organophosphorus chemistry. While examining deoxygenation reactions involving
1540:
789:
399:
As an extension of his earlier research with trivalent phosphorus as an oxygen acceptor, Mukaiyama began to examine the role of metallic catalysts for the
303:
944:"Preparation of Esters of Phosphoric Acid by the Reaction of Trivalent Phosphorus Compounds with Diethyl Azodicarboxylate in the Presence of Alcohols"
763:
672:
during the synthesis of the C ring. This reaction is typically performed at very low temperatures (< -50 Β°C) to stabilize its activated
757:
1530:
638:
was published between the years of 1997 and 1999 after five years of research, making the
Mukaiyama lab the sixth group to report results.
1230:
Iwasawa, N.; Mukaiyama, T. (1983). "Highly enantioselective aldol-type reaction of 3-acetylthiazolidine-2-thione with achiral aldehydes".
385:
leftover from the synthesis of ketene. These vinyloxyboranes proved straightforward to synthesize directly from the desired ketones using
1444:
Mukaiyama, T.; Kobayashi, S.; Kumamoto, T. (1970). "The sulfenylation of the active methylene compounds by the use of sulfenamides".
1175:
381:
with thioboronite produced a beta-hydroxyalkanethioate via a vinyloxyborane intermediate that would perform an aldol reaction with
710:
A total of 145 people earned their doctorates under
Mukaiyama, with 54 eventually becoming professors in various institutions.
477:. In 1982 Mukaiyama showed that tin(II) enolates formed from tin(II) triflate could produce aldol products that were over 95%
396:
group in place of the sulfur. Boron enolates provide an alternative to metal enolates for performing cross-aldol reactions.
458:, it is a cross-aldol reaction between a silyl enol ether (typically derived from a carbonyl of choice using the method of
1535:
730:
1202:
Mukaiyana, T.; Stevens, R. W.; Iwasawa, N. (1982). "Stannous triflate: a new aldol reaction via divalent tin enolates".
1545:
1525:
1483:
522:
1258:
Mukaiyama, T.; Usui, M.; Shimada, E.; Saigo, K. (1975). "A convenient method for the synthesis of carboxylic esters".
1353:
Shiina, I.; Mukaiyama, T. (1994). "A Novel Method for the
Preparation of Macrolides from Ο-Hydroxycarboxylic Acids".
614:
In the early 1990s, at least thirty separate groups were working on the total synthesis of the chemotherapy medicine
645:
which forms the four rings of taxol in the order C, B, A, D. It is differentiated from the others from its use of
734:
635:
125:
1555:
1550:
546:
653:
to create the amide tail. Instead, the tail is created from scratch by converting benzyloxyacetic acid into a
287:
262:
166:
94:
485:
to be covalently bound to the reactants, tin(II) enolates formed from chiral diamine ligands derived from
631:
176:
318:
This framework was expanded to include the formation of a variety of other functional groups, including
793:
745:
767:
724:
589:
403:
207:
17:
751:
658:
451:
112:
505:-methyl-2-chloropyridinium iodide (also called 2-chloro-1-methylpyridinium iodide) allowed for a
1010:"Reaction of Thioboronite. A Convenient Method for the Preparation of Ξ²-Hydroxyalkanethioates"
354:
is an essential tool for synthetic chemists. At its simplest, the aldol reaction involves two
1049:
Mukaiyama, T.; Inomata, K.; Muraki, M. (1972). "Vinyloxyboranes as synthetic intermediates".
269:
in 1953, where he stayed until he received his Ph.D. in synthetic organic chemistry from the
377:
While investigating sulfur-boron compounds in 1971, Mukaiyama reported that the reaction of
1520:
1515:
506:
400:
390:
266:
265:, earning his BSc in synthetic organic chemistry in 1948. He became assistant professor at
161:
1173:
Stork, G.; Hudrlik, P. F. (1968). "Isolation of ketone enolates as trialkylsilyl ethers".
977:"Preparation of Esters of Carboxylic and Phosphoric Acid via Quaternary Phosphonium Salts"
8:
1446:
627:
514:
490:
455:
295:
270:
253:, Mukaiyama helped establish the field of organic chemistry in Japan after World War II.
171:
117:
98:
1107:"Reductive coupling of carbonyl compounds to pinacols and olefins by using TiCl4 and Zn"
897:
662:
573:
as the halogen. In the years since its discovery, a number of different onium salts of
482:
339:
331:
181:
1459:
1479:
1078:
1031:
901:
889:
841:
779:
699:
447:
250:
148:
62:
580:
have been used to catalyze a number of different dehydration reactions, including a
1455:
1426:
1395:
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1299:
1268:
1240:
1212:
1184:
1153:
1119:
1087:
1058:
1021:
988:
955:
924:
879:
831:
773:
677:
654:
642:
619:
562:
530:
474:
431:
415:
312:
306:
reaction, in which a weak acid and weak base catalyze a condensation by means of a
299:
191:
626:
publishing nearly simultaneously in 1994. By then, Mukaiyama had retired from the
681:
669:
596:
566:
510:
435:
327:
246:
1076:
Mukaiyama, T.; Inou, T. (1976). "New cross-aldol reaction via vinyloxyboranes".
623:
478:
351:
1509:
1387:
1035:
738:
649:
as a starting material and for being the only total synthesis not to use the
542:
459:
442:
Mukaiyama again turned to titanium(IV) chloride while seeking an appropriate
298:
employed as a catalyst would react with phosphorus(III) compounds to produce
362:
into either an enol or enolate. However, when both carbonyls are similar in
1414:
1285:
928:
893:
845:
836:
819:
650:
585:
538:
382:
371:
212:
884:
867:
1418:
1355:
1325:
1304:
1287:
1286:
Saigo, K.; Masahiro, U.; Kikuchi, K.; Shimada, E.; Mukaiyama, T. (1977).
1272:
1260:
1257:
1232:
1204:
1158:
1145:
1140:
1124:
1111:
1106:
1026:
1009:
993:
976:
685:
630:
after reaching the mandatory age of 60 and set up an academic lab at the
550:
427:
367:
1430:
1367:
1244:
1216:
1188:
1091:
1062:
960:
943:
454:. Published in 1973 as Mukaiyama was in the process of migrating to the
374:, meaning the reaction may form either cross-products or self-products.
249:. One of the most prolific chemists of the 20th century in the field of
1338:
1320:
615:
603:
443:
291:
1472:
Teruaki
Mukaiyama (1990). "Challenges in Synthetic Organic Chemistry"
1443:
1201:
1400:
1382:
599:
486:
41:
1001:
783:
646:
593:
393:
378:
359:
355:
1138:
1048:
941:
581:
570:
534:
526:
470:
577:
467:
423:
410:. In 1973, he reported that titanium(IV) chloride treated with
323:
319:
1318:
1104:
518:
335:
307:
1495:
673:
574:
521:
linkage. In the initial stage of the process, the carboxyl
411:
386:
764:
ACS Award for Creative work in Synthetic Organic Chemistry
1383:"Creating complexity β the beauty and logic of synthesis"
915:
Mukaiyama, T (1976). "Oxidation-Reduction Condensation".
707:
played an important role in its spread to other nations.
419:
363:
1229:
676:
intermediate and constantly evolves the strong-smelling
481:. In a time when asymmetric reactions largely relied on
302:. This initial example expanded into the concept of the
1352:
1172:
974:
868:"Achievements of the Late Professor Teruaki Mukaiyama"
345:
1288:"New Method for the Preparation of Carboxylic Esters"
1075:
780:
Tetrahedron Prize for Creativity in Organic Chemistry
565:
groups adjacent to the site of the reaction, such as
1507:
1007:
661:, and creating the amide from the alcohol via a
1541:Academic staff of Tokyo Institute of Technology
1496:"Society of Synthetic Organic Chemistry, Japan"
1139:Mukaiyama, T.; Narasaka, K.; Banno, K. (1973).
1008:Mukaiyama, Teruaki; Inomata, Katsuhiko (1971).
942:O. Mitsunobu; M. Yamada; T. Mukaiyama. (1967).
286:Mukaiyama became an assistant professor at the
238:
861:
859:
857:
855:
232:
561:. The reaction gives low yields if there are
914:
865:
1319:Mukaiyama, T.; Usui, M.; Saigo, K. (1976).
1105:Mukaiyama, T.; Sato, T.; Hanna, J. (1973).
1020:(11). The Chemical Society of Japan: 3215.
852:
817:
40:
1399:
1380:
1337:
1303:
1292:Bulletin of the Chemical Society of Japan
1157:
1123:
1051:Bulletin of the Chemical Society of Japan
1025:
1014:Bulletin of the Chemical Society of Japan
992:
981:Bulletin of the Chemical Society of Japan
959:
883:
835:
820:"Obituary: Teruaki Mukaiyama (1927β2018)"
529:atom on the reagent in the presence of a
1176:Journal of the American Chemical Society
618:(Taxol), culminating with the groups of
517:or similar functional groups to form an
446:to activate aldehydes for reaction with
758:Chevalier de lβOrdre National du MΓ©rite
684:nitrogen adjacent to the sulfur in the
592:in the Mukaiyama lab, making use of an
14:
1508:
813:
811:
657:, joining it with benzaldehyde with a
549:reaction with the alcohol reactant as
315:with the loss of a molecule of water.
276:
243:, January 5, 1927 β November 17, 2018)
668:The synthesis also made use of three
557:-alkylpyridinium salts are named the
366:they may both function as either the
1531:Tokyo Institute of Technology alumni
744:Nicholaus Copernicus Medal from the
713:
338:, creating what is now known as the
808:
496:
430:. This is what is now known as the
346:Modifications to the aldol reaction
261:Mukaiyama studied chemistry at the
24:
1321:"The facile synthesis of lactones"
975:Mitsunobu, O.; Yamada, Y. (1967).
641:This total synthesis is largely a
609:
25:
1567:
501:In 1975, Mukaiyama reported that
1488:
1466:
1437:
1408:
1374:
1346:
1312:
1279:
1251:
1223:
1195:
1166:
1132:
725:Chemical Society of Japan Award
636:Mukaiyama taxol total synthesis
569:, but can be improved by using
1098:
1069:
1042:
968:
935:
908:
547:nucleophilic acyl substitution
13:
1:
1460:10.1016/S0040-4039(00)96953-3
801:
553:. Thus, the family of 2-halo-
288:Tokyo Institute of Technology
281:
263:Tokyo Institute of Technology
167:Tokyo Institute of Technology
95:Tokyo Institute of Technology
450:in what became known as the
256:
27:Japanese chemist (1927β2018)
7:
790:Sir Derek Barton Gold Medal
632:Tokyo University of Science
590:namesake macrolactonization
294:, Mukaiyama found that the
239:
177:Tokyo University of Science
10:
1572:
1536:University of Tokyo alumni
794:Royal Society of Chemistry
746:Polish Academy of Sciences
665:followed by benzoylation.
541:and also serves as a good
408:titanium(IV) tetrachloride
1546:Japanese organic chemists
1526:People from Nagano (city)
1141:"New aldol type reaction"
768:American Chemical Society
692:
404:Friedel-Crafts alkylation
233:
221:
200:
190:
154:
144:
137:
105:
90:
82:
70:
48:
39:
32:
752:Person of Cultural Merit
659:Mukaiyama aldol addition
507:dehydration condensation
452:Mukaiyama aldol reaction
126:total synthesis of taxol
113:Mukaiyama aldol addition
489:could achieve over 90%
929:10.1002/anie.197600941
837:10.1002/anie.201902440
537:ester is an activated
1556:21st-century chemists
1551:20th-century chemists
885:10.1002/tcr.202000105
866:Murakami, M. (2021).
602:in the presence of a
1305:10.1246/bcsj.50.1863
1273:10.1246/cl.1975.1045
1159:10.1246/cl.1973.1011
1125:10.1246/cl.1973.1041
1027:10.1246/bcsj.44.3215
994:10.1246/bcsj.40.2380
948:Bull. Chem. Soc. Jpn
917:Angew. Chem. Int. Ed
824:Angew. Chem. Int. Ed
818:Seebach, D. (2019).
391:electron-withdrawing
267:Gakushuin University
162:Gakushuin University
1447:Tetrahedron Letters
1431:10.1246/cl.2001.846
1368:10.1246/cl.1994.677
1245:10.1246/cl.1983.297
1217:10.1246/cl.1982.353
1189:10.1021/ja01018a051
1092:10.1246/cl.1976.559
1063:10.1021/ja00784a079
961:10.1246/bcsj.40.935
872:The Chemical Record
760:from France in 1994
628:University of Tokyo
456:University of Tokyo
414:powder catalyzed a
389:, which has a more
330:in the presence of
296:mercury(II) acetate
277:Research and career
271:University of Tokyo
172:University of Tokyo
118:Mukaiyama hydration
99:University of Tokyo
1381:Nina Hall (2003).
1339:10.1246/cl.1976.49
776:from Japan in 1997
754:from Japan in 1992
663:Mitsunobu reaction
582:macrolactonization
559:Mukaiyama reagents
483:chiral auxiliaries
475:enantioselectivity
426:after reflux with
406:and in particular
340:Mitsunobu reaction
332:triphenylphosphine
304:redox condensation
182:Kitasato Institute
130:redox condensation
122:Mukaiyama reagents
1454:(59): 5115β5118.
1267:(10): 1045β1048.
1183:(16): 4462β4464.
1118:(10): 1041β1044.
1079:Chemistry Letters
987:(10): 2380β2382.
830:(18): 5803β5804.
714:Honors and awards
705:Chemistry Letters
700:Chemistry Letters
448:silyl enol ethers
251:organic synthesis
240:Mukaiyama Teruaki
228:Teruaki Mukaiyama
225:
224:
149:Organic Chemistry
139:Scientific career
74:November 17, 2018
34:Teruaki Mukaiyama
16:(Redirected from
1563:
1500:
1499:
1492:
1486:
1474:Clarendon Press.
1470:
1464:
1463:
1441:
1435:
1434:
1412:
1406:
1405:
1403:
1401:10.1039/b212248k
1378:
1372:
1371:
1350:
1344:
1343:
1341:
1316:
1310:
1309:
1307:
1298:(7): 1863β1866.
1283:
1277:
1276:
1255:
1249:
1248:
1227:
1221:
1220:
1199:
1193:
1192:
1170:
1164:
1163:
1161:
1152:(9): 1011β1014.
1136:
1130:
1129:
1127:
1102:
1096:
1095:
1073:
1067:
1066:
1046:
1040:
1039:
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1005:
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998:
996:
972:
966:
965:
963:
939:
933:
932:
912:
906:
905:
887:
863:
850:
849:
839:
815:
774:Order of Culture
670:Swern oxidations
655:silyl enol ether
643:linear synthesis
620:Robert A. Holton
567:tertiary carbons
563:sterically large
545:in a subsequent
533:. The resulting
497:Namesake reagent
432:McMurry reaction
422:which formed an
418:of carbonyls in
416:pinacol coupling
313:carboxylic acids
300:acetic anhydride
244:
242:
236:
235:
201:Notable students
192:Doctoral advisor
77:
58:
56:
44:
30:
29:
21:
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1137:
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1002:
973:
969:
940:
936:
913:
909:
864:
853:
816:
809:
804:
799:
716:
695:
682:electronegative
612:
610:Taxol synthesis
597:carboxylic acid
511:carboxylic acid
499:
348:
328:carboxylic acid
284:
279:
259:
247:organic chemist
245:was a Japanese
230:
217:
208:Eiichi Nakamura
186:
133:
97:
91:Alma mater
75:
66:
60:
59:January 5, 1927
54:
52:
35:
28:
23:
22:
15:
12:
11:
5:
1569:
1559:
1558:
1553:
1548:
1543:
1538:
1533:
1528:
1523:
1518:
1502:
1501:
1487:
1484:978-0198556442
1465:
1436:
1425:(8): 846β847.
1407:
1394:(6): 661β664.
1373:
1362:(4): 677β680.
1345:
1311:
1278:
1250:
1239:(3): 297β298.
1222:
1211:(3): 353β356.
1194:
1165:
1131:
1097:
1086:(6): 559β562.
1068:
1057:(3): 967β968.
1041:
1000:
967:
954:(4): 935β939.
934:
907:
851:
806:
805:
803:
800:
798:
797:
787:
777:
771:
761:
755:
749:
742:
731:Imperial Prize
728:
721:
715:
712:
694:
691:
624:K. C. Nicolaou
611:
608:
588:developed his
498:
495:
479:stereospecific
352:aldol reaction
347:
344:
283:
280:
278:
275:
258:
255:
223:
222:
219:
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216:
215:
210:
204:
202:
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196:Toshio Hishino
194:
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128:
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115:
109:
107:
106:Known for
103:
102:
92:
88:
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84:
80:
79:
78:(aged 91)
72:
68:
67:
61:
50:
46:
45:
37:
36:
33:
26:
9:
6:
4:
3:
2:
1568:
1557:
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1539:
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1534:
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1511:
1497:
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1478:
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1457:
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1424:
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1411:
1402:
1397:
1393:
1390:
1389:
1388:Chem. Commun.
1384:
1377:
1369:
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1361:
1358:
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1349:
1340:
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1331:
1328:
1327:
1322:
1315:
1306:
1301:
1297:
1293:
1289:
1282:
1274:
1270:
1266:
1263:
1262:
1254:
1246:
1242:
1238:
1235:
1234:
1226:
1218:
1214:
1210:
1207:
1206:
1198:
1190:
1186:
1182:
1178:
1177:
1169:
1160:
1155:
1151:
1148:
1147:
1142:
1135:
1126:
1121:
1117:
1114:
1113:
1108:
1101:
1093:
1089:
1085:
1081:
1080:
1072:
1064:
1060:
1056:
1052:
1045:
1037:
1033:
1028:
1023:
1019:
1015:
1011:
1004:
995:
990:
986:
982:
978:
971:
962:
957:
953:
949:
945:
938:
930:
926:
923:(2): 94β103.
922:
918:
911:
903:
899:
895:
891:
886:
881:
877:
873:
869:
862:
860:
858:
856:
847:
843:
838:
833:
829:
825:
821:
814:
812:
807:
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743:
740:
739:Japan Academy
736:
735:Academy Prize
732:
729:
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723:
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690:
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583:
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543:leaving group
540:
536:
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51:
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31:
19:
1490:
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1468:
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1445:
1439:
1422:
1417:
1410:
1391:
1386:
1376:
1359:
1354:
1348:
1332:(1): 49β50.
1329:
1324:
1314:
1295:
1291:
1281:
1264:
1259:
1253:
1236:
1231:
1225:
1208:
1203:
1197:
1180:
1174:
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1134:
1115:
1110:
1100:
1083:
1077:
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1054:
1050:
1044:
1017:
1013:
1003:
984:
980:
970:
951:
947:
937:
920:
916:
910:
875:
871:
827:
823:
717:
709:
704:
698:
696:
667:
651:Ojima lactam
640:
613:
586:Isamu Shiina
558:
554:
539:electrophile
502:
500:
464:
441:
398:
383:formaldehyde
376:
372:electrophile
360:tautomerized
349:
334:to yield an
317:
285:
260:
227:
226:
213:Isamu Shiina
155:Institutions
138:
76:(2018-11-17)
1521:2018 deaths
1516:1927 births
1419:Chem. Lett.
1356:Chem. Lett.
1326:Chem. Lett.
1261:Chem. Lett.
1233:Chem. Lett.
1205:Chem. Lett.
1146:Chem. Lett.
1112:Chem. Lett.
878:(1): 2β16.
686:sulfenamide
584:. In 1994,
551:nucleophile
473:and induce
428:1,4-dioxane
401:dehydrative
368:nucleophile
83:Citizenship
1510:Categories
802:References
616:paclitaxel
606:catalyst.
604:Lewis acid
509:between a
444:Lewis acid
292:phosphines
282:Early work
55:1927-01-05
1036:0009-2673
902:228101971
792:from the
766:from the
737:from the
600:anhydride
523:displaces
487:L-proline
273:in 1957.
257:Education
18:Mukaiyama
894:33305537
846:30861285
784:Elsevier
647:L-serine
594:aromatic
394:triflate
356:carbonyl
796:in 1998
786:in 1998
770:in 1996
748:in 1986
741:in 1983
727:in 1973
571:bromine
535:pyridyl
527:halogen
515:alcohol
513:and an
471:ligands
436:McMurry
370:or the
101:(Ph.D.)
65:, Japan
1482:
1034:
900:
892:
844:
693:Legacy
634:. The
578:arenes
468:chiral
424:alkene
379:ketene
324:amides
320:esters
145:Fields
63:Nagano
898:S2CID
782:from
519:ester
460:Stork
336:ester
308:redox
234:εε±± ε
ζ
86:Japan
1480:ISBN
1477:2003
1032:ISSN
890:PMID
842:PMID
733:and
674:DMSO
622:and
575:aza-
531:base
525:the
412:zinc
387:DBBT
350:The
322:and
71:Died
49:Born
1456:doi
1427:doi
1396:doi
1364:doi
1334:doi
1300:doi
1269:doi
1241:doi
1213:doi
1185:doi
1154:doi
1120:doi
1088:doi
1059:doi
1022:doi
989:doi
956:doi
925:doi
880:doi
832:doi
678:DMS
420:THF
364:pKa
1512::
1452:11
1450:.
1423:30
1385:.
1360:23
1323:.
1296:50
1294:.
1290:.
1237:12
1209:11
1181:90
1179:.
1143:.
1109:.
1082:.
1055:95
1053:.
1030:.
1018:44
1016:.
1012:.
985:40
983:.
979:.
952:40
950:.
946:.
921:15
919:.
896:.
888:.
876:21
874:.
870:.
854:^
840:.
828:58
826:.
822:.
810:^
493:.
491:ee
434:-
342:.
237:,
1498:.
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1458::
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1429::
1404:.
1398::
1392:6
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1336::
1330:5
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1271::
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1247:.
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1215::
1191:.
1187::
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1156::
1150:2
1128:.
1122::
1116:2
1094:.
1090::
1084:5
1065:.
1061::
1038:.
1024::
997:.
991::
964:.
958::
931:.
927::
904:.
882::
848:.
834::
555:N
503:N
231:(
57:)
53:(
20:)
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