ASYMMETRIC CONJUGATE ADDITIONS TO CHIRAL BICYCLIC LACTAMS - A STEREOSELECTIVE, CONCISE SYNTHESIS OF CHIRAL 2-ALKYL-3,4-AZIRIDINOPYRROLIDINES

被引:11
作者
ANDRES, CJ [1 ]
MEYERS, AI [1 ]
机构
[1] COLORADO STATE UNIV, DEPT CHEM, FT COLLINS, CO 80523 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/0040-4039(95)00573-U
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereoselective, conjugate additions of primary amines to chiral alpha-iodo alpha, beta- unsaturated bicyclic lactams are described. Typical yields of the resulting aziridinolactams ranged from 60-90% with facial diastereoselectivities of >98:2 in all cases. Selected optically pure aziridinobicyclic lactams were transformed, by reductive cleavage, into chiral 2-alkyl, 3, 4-aziridinopyrrolidines.
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页码:3491 / 3494
页数:4
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