Enantioselective cyclopropanation of allylic alcohols with dioxaborolane ligands: Scope and synthetic applications

被引：193

作者：

Charette, AB ^{[1
]}

Juteau, H ^{[1
]}

Lebel, H ^{[1
]}

Molinaro, C ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1998年 / 120卷 / 46期

关键词：

D O I：

10.1021/ja982055v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A very effective chiral controller has been found for the conversion of allylic alcohols into the corresponding enantiomerically enriched cyclopropanes using bis(iodomethyl)zinc. A variety of chiral, nonracemic cyclopropylmethanols could be obtained according to this method. This methodology was extended with success to the cyclopropanation of unconjugated and conjugated polyenes and homoallylic alcohols. The cyclopropanation of allylic carbamates has also been investigated with this system, but it was found that enantioenriched cyclopropylmethylamines are best prepared from enantioenriched cyclopropylmethanols.

引用

页码：11943 / 11952

页数：10

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