ALPHA-(ARYLSULFONAMIDO)BORNEOLS AS AUXILIARIES IN ASYMMETRIC-SYNTHESIS - AN EFFICIENT AND HIGHLY STEREOSELECTIVE METHOD FOR THE REDUCTION OF ALPHA-KETO ESTERS

被引:56
作者
XIANG, YB
SNOW, K
BELLEY, M
机构
[1] Merck Frosst Centre for Therapeutic Research, Quebec, H9R 4P8, P.O. Box 1005, Pointe Claire-Dorval
关键词
D O I
10.1021/jo00057a004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for preparation of enantiomerically pure alpha-hydroxy esters by stereoselective reduction of chiral alpha-keto esters under convenient conditions (LiAlH(OCEt3)3, THF,0-degrees-C) has been developed. The compounds exo,exo-3-(arylsulfonamido)-2-borneol and exo,exo-2-(arylsulfonamido)-3-borneol have been used as novel auxiliaries to achieve highly diastereoselective reductions. The auxiliaries can be removed by mild saponification (LiOH, THF-H2O, rt) without racemization of the reduced products.
引用
收藏
页码:993 / 994
页数:2
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