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Copper-Catalyzed Asymmetric Conjugate Addition of Grignard Reagents to Trisubstituted Enones. Construction of All-Carbon Quaternary Chiral Centers

Supporting Info

David Martin,^† Stefan Kehrli,^† Magali d'Augustin,^† Hervé Clavier,^‡ Marc Mauduit,*^‡ and Alexandre Alexakis*^†

Dpartement de Chimie Organique, Universit de Genve, 30, quai Ernest Ansermet CH-1211 Genve 4, Switzerland, and UMR CNRS 6226 Sciences Chimiques de Rennes, Ecole Nationale Suprieure de Chimie de Rennes, Av. du Gnral Leclerc, 35700 Rennes, France

J. Am. Chem. Soc., 2006, 128 (26), pp 8416–8417

DOI: 10.1021/ja0629920

Publication Date (Web): June 14, 2006

†

Université de Genève.

‡

Ecole Nationale Supérieure de Chimie de Rennes.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, alexandre.alexakis@chiorg.unige.ch

Abstract

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.

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Published In Issue July 05, 2006
Received April 29, 2006

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Communication

Copper-Catalyzed Asymmetric Conjugate Addition of Grignard Reagents to Trisubstituted Enones. Construction of All-Carbon Quaternary Chiral Centers