ASYMMETRIC-SYNTHESIS OF N-METHYL-ALPHA-AMINO ESTERS FROM A GLYOXAL DERIVED CHIRAL HETEROCYCLE

被引：32
作者：
AGAMI, C
COUTY, F
PRINCE, B
PUCHOT, C
机构：
[1] Laboratoire de Chimie Organique (URA CNRS 408), Université P.et M. Curie, 75005 Paris
来源：
TETRAHEDRON | 1991年 / 47卷 / 25期
关键词：
D O I：
10.1016/S0040-4020(01)87103-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction between a chiral template derived from glyoxal with organometallic reagents leads ultimately to the optically active tile compounds. The sterochemical outcome of the key-step which involves substitution of a thiophenol group depends on the organometallic: predominantly inversion with alkyl copper or complete retention with alkyl zinc halides. The stereodirecting effect of an allylic hydroxy group in an iminium intermediate is evidenced in the case of the organozinc reagent.
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页码：4343 / 4354
页数：12
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