Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Asymmetric Reactions. III. Stereoselectivity Difference between Grignard and Alkyllithium Reactions with 2,3-O-Substituted-D-glyceraldehydes
Yoshiaki OhgoJuji YoshimuraMasami KonoTetsuo Sato
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1969 Volume 42 Issue 10 Pages 2957-2961

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Abstract

Stereoselectivity has been investigated in addition reactions of 2,3-O-isopropylidene-D-glyceraldehyde (I) or 2,3-di-O-benzyl-D-glyceraldehyde (II) with phenylmagnesium bromide or phenyllithium. Stereoselectivity difference between the Grignard and phenyllithium reactions occurred in the case of compound (I): the phenyllithium reaction gives threo and the Grignard reaction erythro products predominantly. On the other hand, no difference in stereoselectivity has been observed between the reactions with 2,3-di-O-benzyl-D-glyceraldehyde (II): both reactions gave threo product predominantly.

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