STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED TETRAHYDROFURANS VIA SELENOETHERIFICATION OF 2-SILYL-3-ALKENOLS - A STUDY OF ALLYLIC STEREOCONTROL

被引：42

作者：

LANDAIS, Y

PLANCHENAULT, D

WEBER, V

机构：

[1] Institut de Chimie Organique, Université de Lausanne Collège Propédeutique

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 17期

关键词：

D O I：

10.1016/0040-4039(95)00410-E

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-endo-trig selenoetherifications of substituted 2-silyl-3-alkenols gave tri- or tetrasubstituted 2,4-cis tetrahydrofurans in moderate to good yields with excellent diastereoselectivities. Opposite stereoselectivities were found with an analogous allylic diol. A transition state model has been proposed to rationalize this stereochemical outcome.

引用

页码：2987 / 2990

页数：4

共 30 条

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