Copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers

被引:249
作者
Martin, David
Kehrli, Stefan
d'Augustin, Magali
Clavier, Herve
Mauduit, Marc
Alexakis, Alexandre
机构
[1] Univ Geneva, Dept Chim Organ, CH-1211 Geneva 4, Switzerland
[2] Ecole Natl Super Chim Rennes, CNRS, UMR 6226, F-35700 Rennes, France
关键词
D O I
10.1021/ja0629920
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted cyclic enones affords enantioenriched all-carbon quaternary centers with up to 96% ee. The chiral ligand is a diaminocarbene, directly generated in situ. The combination of Grignard reagent and diaminocarbene is unprecedented in conjugate addition, and the additon of the phenyl group, on such enones, cannot be done by other conjugate addition methods. Copyright © 2006 American Chemical Society.
引用
收藏
页码:8416 / 8417
页数:2
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