1,3-ASYMMETRIC INDUCTION IN THE REDUCTION OF ALPHA-ALKYL BETA-KETOSULFOXIDES WITH DIBAL/ZNBR2

被引：0
|
作者：
BARROS, D [1 ]
CARRENO, MC [1 ]
RUANO, JLG [1 ]
MAESTRO, MC [1 ]
机构：
[1] UNIV AUTONOMA MADRID,FAC CIENCIAS,DEPT QUIM CI,CANTOBLANCO,E-28049 MADRID,SPAIN
来源：
TETRAHEDRON LETTERS | 1992年 / 33卷 / 19期
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D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The highly stereoselective reduction of chiral alpha-alkyl beta-ketosulfoxides with DIBAL/ZnBr2 is governed by the configuration at the sulfur (1-3-induction) and not by that of the C-alpha (1,2-induction) as it has been previously reported. This fact considerably increases the scope of the Solladie's methodology to synthesize optically pure secondary carbinols. Those substituents decreasing the capability of the carbonyl oxygen to chelate the ZnBr2 induce a decrease in the stereoselectivity.
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页码：2733 / 2736
页数：4
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