Improved Zinc-Catalyzed Simmons-Smith Reaction: Access to Various 1,2,3-Trisubstituted Cyclopropanes

被引：49

作者：

Levesque, Eric ^{[1
]}

Goudreau, Sebastien R. ^{[1
]}

Charette, Andre B. ^{[1
]}

机构：

[1] Univ Montreal, FAS Dept Chem, Ctr Green Chem & Catalysis, Stn Downtown, Montreal, PQ H3C 3J7, Canada

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 05期

基金：

加拿大自然科学与工程研究理事会;

关键词：

1,2,3-SUBSTITUTED CYCLOPROPANES; ENANTIOSELECTIVE SYNTHESIS; REAGENTS; DECOMPOSITION; BIOSYNTHESIS; STABILITY; STRATEGY;

D O I：

10.1021/ol500267w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Simmons-Smith reaction of zinc carbenoids with alkenes is a powerful method to access cyclopropanes containing various substitution patterns. This work exploits the high reactivity of aryldiazomethanes toward zinc halides to generate aryl-substituted carbenoids catalytically. These carbenoids are able to cyclopropanate various alkenes diastereoselectively, including unfunctionalized substrates such as styrenes. The zinc catalyst can be modified to tolerate the use of free allylic alcohols.

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页码：1490 / 1493

页数：4

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