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Copper-Catalyzed Enantioselective Conjugate Addition of Grignard Reagents to α,β-Unsaturated Esters

Fernando López, Syuzanna R. Harutyunyan, Auke Meetsma, Adriaan J. Minnaard, Ben L. Feringa*

*Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands, Email: b.l.feringarug.nl

F. Lopez, S. R. Harutyunyan, A. Meetsma, A. J. Minnaard, B. L. Feringa, Angew. Chem. Int. Ed., 2005, 44, 2752-2756.

DOI: 10.1002/anie.200500317


Abstract

Inexpensive and readily available Grignard reagents and stable dinuclear Cu complexes can be used for the catalytic enantioselective conjugate addition to simple acyclic α,β-unsaturated methyl esters providing β-substituted chiral esters in good yields and with excellent enantioselectivities.

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Key Words

asymmetric catalysis, conjugate addition, copper, enantioselectivity, Grignard reagents


ID: J06-Y2005-450