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Synfacts 2007(11): 1162-1162  
DOI: 10.1055/s-2007-991264
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Conjugate Addition to 2- or 3-Substituted Cylcopent-2-en-1-ones

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
M. Vuagnoux-d’Augustin, S. Kehrli, A. Alexakis*
Université de Genève, Switzerland
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Publication History

Publication Date:
23 October 2007 (online)

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Significance

This paper describes the synthesis of enantioenriched, all-carbon quaternary stereocenters. A variety of both 2- and 3-substituted cyclopentenone substrates work well in this reaction. The use of phosphoramidite ligands 1 or 2 with a Cu(OTf)2 source gave high conversion with good enantioselectivity. Michael addition reactions are one of the best synthetic routes for this purpose but truly reliable asymmetric processes are still not far developed.