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
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
收藏
页码:11295 / 11308
页数:14
相关论文
共 24 条