STEREOCONTROL IN ORGANIC-SYNTHESIS USING SILICON-COMPOUNDS

被引：30

作者：

FLEMING, I

机构：

[1] University Chemical Laboratory, Cambridge CB2 1EW, Lensfield Road

来源：

PURE AND APPLIED CHEMISTRY | 1990年 / 62卷 / 10期

关键词：

D O I：

10.1351/pac199062101879

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereogenic centre carrying a silyl group, a carbon substituent, and a hydrogen atom adjacent to a double bond (1) induces highly diastereoselective attack by electrophiles. The reasons for the effectiveness of this combination and its limitations are discussed, and illustrated by electrophilic substitution reactions (3) and the hydroboration (4) of allylsilanes, and enolate alkylations of esters having a β-silyl group (5). Studies directed towards the synthesis of ebelactone-a (17) illustrate how well and with what versatility the silyl group can control relative stereochemistry. © 1990, IUPAC.

引用

页码：1879 / 1886

页数：8

共 44 条

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