Metal-catalyzed silacyclopropanation of mono- and disubstituted alkenes

被引：64

作者：

Cirakovic, J ^{[1
]}

Driver, TG ^{[1
]}

Woerpel, KA ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 32期

关键词：

D O I：

10.1021/ja020566i

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

As an alternative to the strongly reducing conditions necessary for the formation of silacyclopropanes, silylene transfer was developed as a mild, functional group tolerant method of silacyclopropanation. Complex silacyclopropanes were formed from functionalized alkenes using cyclohexane di-tert-butyl silacyclopropane, 1, as the source of t-Bu2Si. Di-tert-butyl silylene can be generated from 1 through the use of a catalytic amount of a metal salt. At -27 °C, silver triflate catalyzes the transfer of t-Bu2Si from 1 to mono- and disubstituted alkenes stereospecifically and diastereoselectively. In situ functionalization of silacyclopropanes with catalytic zinc bromide and methyl formate provides for an expedient one-flask synthesis of complex oxasilacyclopentanes from alkenes. Copyright © 2002 American Chemical Society.

引用

页码：9370 / 9371

页数：2

共 18 条

[1] A stable silylene in a reactive environment:: Synthesis, reactivity, and silicon extrusion chemistry of a coordinatively unsaturated ruthenium silylene complex containing chloride and η3-P-C-P ligands [J].