A simple and efficient diastereoselective Strecker synthesis of optically pure α-arylglycines

被引：32

作者：

Dave, RH ^{[1
]}

Hosangadi, BD ^{[1
]}

机构：

[1] Univ Bombay, Dept Chem, Bombay 400098, Maharashtra, India

来源：

TETRAHEDRON | 1999年 / 55卷 / 37期

关键词：

asymmetric Strecker reaction; 1,3 induction; (R)-2-amino-2-phenylethanol; alpha-arylglycines;

D O I：

10.1016/S0040-4020(99)00673-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and economical method for the synthesis of highly functionalised alpha-amino nitriles, precursors to alpha-arylglycines with high optical purity is reported. For this purpose, (R) or (S)-2-amino-2-phenylethanol were used as chiral auxiliaries in a 1,3 Strecker reaction. Reactions were studied with a broad range of reagent systems for the generation of cyano nucleophile. Methodology has been extended for the synthesis of (S)-alpha-(2-iodo-5-nitrophenyl)glycine, (S)-alpha-(4-methoxyphenyl)glycine and (R)-beta-(4-methoxyphenyl)alanine. (C) 1999 Published by Elsevier Science Ltd. ALI rights reserved.

引用

页码：11295 / 11308

页数：14

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