THE PRODUCT OF BAKERS-YEAST REDUCTION OF ETHYL 2-CHLORO-3-OXOBUTANOATE AS A PRECURSOR OF THE 1-ETHOXYCARBONYL 2(S)-HYDROXYPROPYL RADICAL

被引：13
|
作者：
HAMDANI, M [1 ]
DEJESO, B [1 ]
DELEUZE, H [1 ]
SAUX, A [1 ]
MAILLARD, B [1 ]
机构：
[1] UNIV BORDEAUX 1,CHIM ORGAN LAB,CNRS,URA 35,351 COURS LIBERAT,F-33405 TALENCE,FRANCE
来源：
TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 06期
关键词：
D O I：
10.1016/S0957-4166(00)80233-5
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Baker's yeast treatment of ethyl 2-chloro-3-oxobutanoate 1, diethyl 2-acetylmalonate 2 and ethyl 2-cyano-3-oxobutanoate 3 was effected in order to obtain enantiomerically enriched compounds. In contrast to the reaction of 2 and 3, efficient diastereo- and enantioselective reduction of 1 provided ethyl 2(R)-chloro-3(S)-hydroxybutanoate. This product was used as precursor of the 1-ethoxycarbonyl-2(S)-hydroxypropyl radical and the diastereoselectivity of the addition of this intermediate to alkenes was studied.
引用
收藏
页码：1233 / 1236
页数：4
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