STEREOSELECTIVE SYNTHESIS OF VICINAL DIAMINES

被引：151
作者：
REETZ, MT
JAEGER, R
DREWLIES, R
HUBEL, M
机构：
[1] Fachbereich Chemie, Universität Marburg, W-3550, Hans-Meerwein-Strasse
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1991年 / 30卷 / 01期
关键词：
D O I：
10.1002/anie.199101031
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
alpha-Amino aldimines such as 1, which are readily accessible from amino acids, react with alkyllithium and -cerium compounds in a chelation-controlled manner to give the vicinal diamines 2 in optical yields of up to 90%. However, if the donor strength of the aldimine nitrogen atom is weakened by the electron-withdrawing tosyl group, the chelation effect is suppressed and reaction with Grignard reagents gives preferentially the stereoisomeric adducts with opposite relative configuration. Bn = benzyl.
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页码：103 / 106
页数：4
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