Asymmetric induction in the nucleophile addition to eta(6)-arene-tricarbonyl-chromium(0) complexes

被引:41
作者
Semmelhack, MF
Schmalz, HG
机构
[1] Department of Chemistry, Princeton University, Princeton
[2] Institute for Organic Chemistry, Technische Universitat Berlin, D-10623 Berlin
关键词
D O I
10.1016/0040-4039(96)00572-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The addition of 2-lithio-2-methylpropionitrile (1) to chirally modified eta(6)-arene-tricarbonylchromium complexes (5) leads to the formation of 2-(cyclohex-2-en-1-on-5-yl)-2-methylpropionitrile (4) in good yields and, under thermodynamically controlled conditions, with up to 48% ee. Copyright (C) 1996 Published by Elsevier Science Ltd
引用
收藏
页码:3089 / 3092
页数:4
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