Diastereoselective temporary silicon-tethered ring-closing-metathesis reactions with prochiral alcohols: A new approach to long-range asymmetric induction

被引：56

作者：

Evans, PA ^{[1
]}

Cui, B

Buffone, GP

机构：

[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

[2] Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 15期

关键词：

cyclization; diastereoselectivity; medium-sized rings; metathesis; silicon;

D O I：

10.1002/anie.200250486

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A useful approach to 1,4-, 1,5-, and 1,6-stereocontrol, diastereoselective ring-closing-metathesis reactions that utilize temporary silicon tethers represent a new strategy for long-range asymmetric induction. This method facilitates the construction of cis-1,4-silaketals (n = 0, d.r. = 20:1; see scheme), whereas the extension of this concept to higher alkenyl alcohols (n = 1-4) results in a reversal of diastereoselectivity that favors formation of the trans isomer.

引用

页码：1734 / 1737

页数：4

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