ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES

被引:153
作者
CAIN, CM [1 ]
COUSINS, RPC [1 ]
COUMBARIDES, G [1 ]
SIMPKINS, NS [1 ]
机构
[1] UNIV LONDON QUEEN MARY COLL,DEPT CHEM,LONDON E1 4NS,ENGLAND
关键词
D O I
10.1016/S0040-4020(01)85435-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A number of chiral secondary amines have been prepared and used as precursors to the corresponding chiral lithium amide bases. Treatment of either cis-2,6-dimethylcyclohexanone or 4-tert-butylcyclohexanone with a chiral lithium amide, followed by electrophilic quench, gives chiral products in up to 88% enantiomeric excess. The results with 4-tert-butylcyclohexanone are in disagreement with an earlier literature report, giving products of lower enantiomeric excess but higher optical rotation. © 1990.
引用
收藏
页码:523 / 544
页数:22
相关论文
共 28 条