Bis(oxazoline)-copper(I)-catalyzed enantioselective cyclopropanation of cinnamate esters with diazomethane

被引：34

作者：

Charette, AB ^{[1
]}

Janes, MK ^{[1
]}

Lebel, H ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 07期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0957-4166(03)00076-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral bis(oxazoline)-copper(l) complexes were found to be effective catalysts for the enantioselective cyclopropanation reaction of trans-cinnamate esters exploiting an argon flow mediated diazomethane addition method. After optimization of the catalyst structure, good yields and enantiomeric excesses were obtained with electron-poor methyl cinnamate derivatives. Sterically demanding esters gave lower yields and enantioselectivities. The correlation between the product enantiopurities and the sigma(+) values of the aromatic para-substituents was shown to be linear in a Hammet-type plot. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：867 / 872

页数：6

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