Addition of organolithium reagents to some carbohydrate enones

被引：9
|
作者：
Achmatowicz, O [1 ]
Szechner, B [1 ]
Maurin, JK [1 ]
机构：
[1] INST ATOM ENERGY,PL-05400 OTWOCK,POLAND
来源：
TETRAHEDRON | 1997年 / 53卷 / 17期
关键词：
ALPHA-ENONES;
D O I：
10.1016/S0040-4020(97)00253-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Addition of organolithium reagents to the sugar enones: alkyl 2,3,6-trideoxy-alpha-L- and 2,3-dideoxy-alpha-D-hex-2-enopyranosid-4-ulose has been examined. Butyl, benzyl and 2,5-dimethoxy-4-methylphenyllithium add with increasing stereoselectivity, to the carbonyl group of the alpha,beta-unsaturated ketosugars, whereas 2,5-dimethoxybenzyllithium undergoes stereospecific conjugate addition and 1,2-addition in the ratio of 1.7:1. The structure of the resultant carbinols is based on X-ray crystallographic evidence. (C) 1997 Published by Elsevier Science Ltd.
引用
收藏
页码：6035 / 6044
页数：10
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