Copper Catalyzed Asymmetric Synthesis of Chiral Allylic Esters

Koen Geurts, Stephen P. Fletcher and 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

K. Geurts, S. P. Fletcher, B. L. Feringa, J. Am. Chem. Soc., 2006, 128, 15572-15573.

DOI: 10.1021/ja065780b

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Abstract

A chemo- and regioselective, Cu-catalyzed asymmetric addition of Grignard reagents to 3-bromopropenyl esters provides allylic esters in high yields and enantioselectivities using Taniaphos as ligand. The method is a practical route to chiral, nonracemic allylic alcohols.

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Synthesis of Optically Active Bifunctional Building Blocks through Enantioselective Copper-Catalyzed Allylic Alkylation Using Grignard Reagents

A. W. van Zijl, F. López, A. J. Minnaard, B. L. Feringa, J. Org. Chem., 2007, 72, 2558-2563.

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Key Words

allylic alcohols, allylation

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ID: J48-Y2006-4000