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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 05期

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.

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页码：993 / 994

页数：2

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