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Bidentate Hydroxyalkyl NHC Ligands for the Copper-Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Grignard Reagents

Authors

  • Magaly Magrez,

    1. Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Av. du Général Leclerc, CS 50837, 35708 Rennes Cedex 7 (France), Fax: (+33) 223238108
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  • Yann Le Guen,

    1. Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Av. du Général Leclerc, CS 50837, 35708 Rennes Cedex 7 (France), Fax: (+33) 223238108
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  • Dr. Olivier Baslé,

    1. Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Av. du Général Leclerc, CS 50837, 35708 Rennes Cedex 7 (France), Fax: (+33) 223238108
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  • Dr. Christophe Crévisy,

    Corresponding author
    1. Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Av. du Général Leclerc, CS 50837, 35708 Rennes Cedex 7 (France), Fax: (+33) 223238108
    • Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Av. du Général Leclerc, CS 50837, 35708 Rennes Cedex 7 (France), Fax: (+33) 223238108
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  • Dr. Marc Mauduit

    Corresponding author
    1. Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Av. du Général Leclerc, CS 50837, 35708 Rennes Cedex 7 (France), Fax: (+33) 223238108
    • Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Av. du Général Leclerc, CS 50837, 35708 Rennes Cedex 7 (France), Fax: (+33) 223238108
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Abstract

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Demonstrating their potential: Bidentate alkoxy NHC ligands have been used in the copper-catalyzed asymmetric allylic alkylation of allyl phosphates with Grignard reagents (see scheme). The method provides access to tertiary and quaternary chiral centers with high regio- and enantioselectivity. The system is also applied to the synthesis of chiral E,E-dienes, a key structural motif prevalent in natural products.

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