Significant asymmetric amplification in enantioselective Cu/DiPPAM-catalyzed 1,6- and 1,4-conjugate additions of diethylzinc to (di)enones.

Org Lett

Ecole Nationale Supérieure de Chimie de Rennes , CNRS, UMR 6226, Avenue du Général Leclerc, CS 50837, 35708 Rennes Cedex 7, France, Department of Organic Chemistry, University of Geneva , Quai Ernest Ansermet 30, 1211 Geneva, Switzerland, and Université Européenne de Bretagne, 5 Bd Laënnec, 35000 Rennes, France.

Published: July 2012

An unprecedented and strong positive nonlinear effect (NLE) was observed in Cu/DiPPAM-catalyzed asymmetric 1,6-conjugate addition of Et2Zn on (E)-3-(prop-1-en-1-yl)cyclohex-2-enone (71% ee reached with a 40% ee ligand). Moreover, similar behaviors were observed in Cu/DiPPAM-catalyzed 1,4-asymmetric conjugate additions of Et2Zn on both cyclohexenone and (E)-3-non-3-en-2-one (83% and 70% ee, respectively, reached with a 40% ee ligand).

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Source
http://dx.doi.org/10.1021/ol300866pDOI Listing

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