Catalytic, enantioselective, conjugate alkyne addition

被引:164
作者
Knöpfel, TF [1 ]
Zarotti, P [1 ]
Ichikawa, T [1 ]
Carreira, EM [1 ]
机构
[1] ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
关键词
D O I
10.1021/ja052411r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We document a copper-catalyzed, enantioselective, conjugate addition involving the direct use of a terminal acetylene, which undergoes in situ metalation. The addition reactions of phenylacetylene to Meldrum's acid derived acceptors take place in aqueous media, without recourse to inert atmosphere. The success of the enantioselective process was enabled by the use of a new class of conveniently accessed P,N-ligands, which we have termed PINAP. These modular ligands are responsive to numerous electronic and steric modifications that permit optimization of the reaction. Copyright © 2005 American Chemical Society.
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页码:9682 / 9683
页数:2
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