Enantioselective catalytic cyclopropanation of styrenes by copper complexes with chiral pinene-[5,6]-bipyridine ligands

被引：70

作者：

Lötscher, D

Rupprecht, S

Stoeckli-Evans, H

von Zelewsky, A ^{[1
]}

机构：

[1] Univ Fribourg, Inst Inorgan & Analyt Chem, CH-1700 Fribourg, Switzerland

[2] Univ Neuchatel, Inst Chem, CH-2000 Neuchatel, Switzerland

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 21期

关键词：

D O I：

10.1016/S0957-4166(00)00401-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Substituted mono- and bis-pinene-[5,6]-bipyridines are useful ligands in asymmetric copper-catalyzed cyclopropanation by styrenes. Copper complexes were prepared either in situ or prior to the reaction. The catalytic reaction of styrene with ethyl diazoacetate and Cu-11b yields ethyl trans-phenylcyclopropane carboxylate in >99% yield and 87% e.e. at 0 degreesC. The corresponding cis-configured cyclopropane was produced with an e.e. of 90%. The cis/trans ratio is 22:78. Other ligands of this series are less effective, Various olefins were tested as substrates but exo-methylene olefins show the best results. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4341 / 4357

页数：17