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

页码：6035 / 6044

页数：10

共 28 条

[1]

ACHMATOWICZ O, 1976, TETRAHEDRON LETT, P1205

[2]

DUAX WL, 1975, ATLAS STEROID STRUCT, P16

[3] CATALYTIC TELOMERIZATION REACTION OF ETHYLENE WITH AROMATIC HYDROCARBONS [J].