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to give a racemic reaction product (assuming an achiral starting material is employed). This approach takes advantage of the fact that when using the
Sharpless alkaloid ligands, the dihydroxylation of alkenes is faster and higher yielding than in their absence. This phenomenon became known as
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byproduct formation. One of the peculiarities of the dihydroxylation of olefins is that the standard "racemic" method (the Upjohn dihydroxylation) is slower and often lower yielding than the asymmetric method (the
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Prior to this method, use of stoichiometric amounts of the toxic and expensive reagent osmium tetroxide was often necessary. The Upjohn dihydroxylation is still often used for the formation of
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Eames, Jason; Mitchell, Helen J.; Nelson, Adam; o'Brien, Peter; Warren, Stuart; Wyatt, Paul (1999). "An efficient protocol for
Sharpless-style racemic dihydroxylation".
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In response to these problems, Stuart Warren and co-workers employed similar reaction conditions to the
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Vanrheenen, V.; Kelly, R. C.; Cha, D. Y. (1976). "An improved catalytic OsO
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88:. It was developed by V. VanRheenen, R. C. Kelly and D. Y. Cha of the
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193:-1,2-glycols using tertiary amine oxides as the oxidant".
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121:-vicinal diols; however, it can be slow and is prone to
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107:. It is superior to previous catalytic methods.
147:"ligand accelerated catalysis", a term coined by
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103:(NMO) as stoichiometric re-oxidant for the
92:in 1976. It is a catalytic system using
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134:Improvements to Upjohn dihydroxylation
166:Sharpless asymmetric dihydroxylation
140:Sharpless asymmetric dihydroxylation
128:Sharpless asymmetric dihydroxylation
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224:J. Chem. Soc., Perkin Trans. 1
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208:10.1016/S0040-4039(00)78093-2
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262:Organic oxidation reactions
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49:Organic Chemistry Portal
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189:oxidation of olefins to
19:Upjohn dihydroxylation
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68:Upjohn dihydroxylation
54:upjohn-dihydroxylation
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161:Milas hydroxylation
257:Addition reactions
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97:-methylmorpholine
74:which converts an
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202:(23): 1973–1976.
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38:Addition reaction
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44:Identifiers
24:Named after
251:Categories
172:References
155:See also
83:vicinal
123:ketone
101:-oxide
76:alkene
70:is an
78:to a
229:1999
86:diol
66:The
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191:cis
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119:cis
80:cis
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99:N
95:N
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