Asymmetric conjugate addition to α-halo enones:: Dramatic effect of styrene on the enantioselectivity

被引:49
作者
Li, Kangying [1 ]
Alexakis, Alexandre [1 ]
机构
[1] Univ Geneva, Dept Chim Organ, CH-1211 Geneva 4, Switzerland
关键词
asymmetric synthesis; conjugate addition; copper; homogeneous catalysis; radicals;
D O I
10.1002/anie.200602417
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple trick could prove generally valuable for asymmetric copper-catalyzed conjugate addition reactions. It was found that the enantioselectivities of such reactions of dialkyl zinc reagents with α-halo enones in the presence of chiral phosphorimidite ligands were dramatically improved upon the addition of styrene, which acts as a radical scavenger to suppress the competitive non-asymmetric radical pathway (see example). (Chemical Equation Presented) © 2006 Wiley-VCH Verlag GmbH &. Co. KGaA.
引用
收藏
页码:7600 / 7603
页数:4
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