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

Anthoni W. van Zijl, Fernando López, Adriaan J. Minnaard and Ben L. Feringa*

*Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747AG, Groningen, The Netherlands, Email: B.L.Feringarug.nl

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

DOI: 10.1021/jo0625655 (free Supporting Information)


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Abstract

Enantioselective copper-catalyzed allylic alkylations of Grignard reagents were performed on allylic bromides with a protected hydroxyl or amine functional group using Taniaphos as a ligand. The terminal olefin moiety in the products can be transformed into various functional groups without racemization.

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Copper Catalyzed Asymmetric Synthesis of Chiral Allylic Esters

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


Key Words

Allylation, Grignard Reagents


ID: J42-Y2007-1020