Reversal of the stereochemical course of the addition of phenylmagnesium bromide to N-benzylimines derived from R-glyceraldehyde depending on the O-protecting group and its application to the synthesis of both enantiomers of phenylglycine

被引：47

作者：

Badorrey, R ^{[1
]}

Cativiela, C ^{[1
]}

DiazdeVillegas, MD ^{[1
]}

Galvez, JA ^{[1
]}

机构：

[1] UNIV ZARAGOZA,CSIC,INST CIENCIA MAT ARAGON,DEPT QUIM ORGAN,E-50009 ZARAGOZA,SPAIN

来源：

TETRAHEDRON | 1997年 / 53卷 / 04期

关键词：

D O I：

10.1016/S0040-4020(96)01053-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The N-Benzyl imines derived from 2,3-di-O-benzyl-D-glyceraldehyde and 2,3-di-O-isopropylidene-D-glyceraldehyde reacted with phenylmagnesium bromide to afford fully protected aminodiols with total diastereoselectivity. The stereochemical course of the addition reaction depends on the nature of the O-protecting group. These compounds can be easily transformed to enantiomerically pure (R) and (S)alpha-phenylglycine. (C) 1997, Elsevier Science Ltd.

引用

页码：1411 / 1416

页数：6

共 25 条

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