First enantioselective catalyst based on a chiral terpyridine:: synthesis of new C2-symmetric 2,2′:6′,2"-terpyridine ligands and copper-catalyzed enantioselective cyclopropanation of alkenes

被引：62

作者：

Kwong, HL ^{[1
]}

Lee, WS ^{[1
]}

机构：

[1] City Univ Hong Kong, Dept Biol & Chem, Kowloon, Hong Kong, Peoples R China

来源：

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

关键词：

D O I：

10.1016/S0957-4166(00)00182-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

New C-2-symmetric chiral 2,2':6',2 "-terpyridines were prepared from readily available homochiral materials. Copper complexes of these ligands were prepared in situ and their catalytic activities in cyclopropanations of alkenes with alkyl diazoacetate to give cyclopropyl esters were studied. In all cases, the cyclopropyl ester yields were excellent and enantioselectivities up to 94% ee were observed. Competition experiments revealed that electron-donating substituents on styrene accelerate the reaction. A Hammett plot exhibited a good linearity with a negative rho(+) value (-0.79). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2299 / 2308

页数：10

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