SYNTHESIS OF HOMOCHIRAL 3-SUBSTITUTED GLUTAMIC ACIDS AND PROLINES FROM PYROGLUTAMIC ACID

被引：52

作者：

HERDEIS, C ^{[1
]}

HUBMANN, HP ^{[1
]}

LOTTER, H ^{[1
]}

机构：

[1] UNIV MUNICH,INST PHARMAZEUT BIOL,D-80333 MUNICH,GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 03期

关键词：

D O I：

10.1016/S0957-4166(00)86204-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Efficient syntheses of (2S,3S)-methylproline (5a) and (2S,3R)-phenylproline (5b) are described, starting from the readily available pyroglutaminol derivatives 2a and 2b via conjugate 1-4-addition of organocuprates to 1. Catalytic hydrogenation of 3 from the least hindered alpha-side furnishes 6, which is transformed to (2S,3R)-methylproline (7). 3-Substituted glutamic acids 8c,d are provided by a four step procedure from 2c,d.

引用

页码：351 / 354

页数：4

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