Asymmetric induction in the arenethiolatocopper(I)-catalyzed substitution reaction of Grignard reagents with allylic substrates

被引：72

作者：

Meuzelaar, GJ

Karlström, ASE

van Klaveren, M

Persson, ESM

del Villar, A

van Koten, G

Bäckvall, JE

机构：

[1] Univ Utrecht, Dept Met Mediated Synth, Debye Inst, NL-3584 CH Utrecht, Netherlands

[2] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden

来源：

TETRAHEDRON | 2000年 / 56卷 / 18期

关键词：

asymmetric induction; copper catalysis; allylic substitution; cross-coupling;

D O I：

10.1016/S0040-4020(00)00145-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The influence of some experimental parameters on the regio- and enantioselectivity in the gamma-selective substitution reaction of Grignard reagents RMgX with acyclic allylic acetates catalyzed by the arenethiolatocopper(I) complex (S)-1 was studied. When more bulky arenethiolatocopper(I) complexes than (S)-1 were employed in a reaction of allylic acetate 3 with n-BuMgI, the enantioselectivities observed for the gamma-product were lower. With an arenethiolatocopper(I) catalyst prepared in situ, several Grignard reagents were studied in a substitution reaction with acetate 2. Compared to n-BuMgI, more bulky Grignard reagents gave no improvement of the enantioselectivity in the formation of the gamma-product. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2895 / 2903

页数：9

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