TMSCl-Mediated catalytic carbocupration of alkynoates: An unprecedented and remarkable effect of catalyst loading on highly selective stereochemical induction via a TMS-allenoate intermediate

被引:19
作者
Jennings, MP [1 ]
Sawant, KB [1 ]
机构
[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA
关键词
carbocupration; cuprates; grignard reaction; propiolates; TMS-allenoate;
D O I
10.1002/ejoc.200400314
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The TMSCl-mediated catalytic carbocupration of alkynoates has been investigated. It has been shown that catalyst loadings as low as 30 mol% readily allow for high yields and diastereoselectivities for a series of Grignard reagents. In addition, an unprecedented and remarkable effect of catalyst loading on stereochemical induction has been observed. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
引用
收藏
页码:3201 / 3204
页数:4
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