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Catalytic Selective Oxyamidation of Cyclic Enamides using Nitrenes

Authors

  • Nicolas Gigant,

    1. Institut de Chimie Organique et Analytiqe, UMR6005 CNRS, Université d'Orléans, 45067 Orléans Cedex 2 (France), Fax: (+33) 2 3841 7281
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  • Geoffroy Dequirez,

    1. Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301 CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette (France), Fax: (+33) 1-6907-7247
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  • Dr. Pascal Retailleau,

    1. Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301 CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette (France), Fax: (+33) 1-6907-7247
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  • Prof. Isabelle Gillaizeau,

    Corresponding author
    1. Institut de Chimie Organique et Analytiqe, UMR6005 CNRS, Université d'Orléans, 45067 Orléans Cedex 2 (France), Fax: (+33) 2 3841 7281
    • Institut de Chimie Organique et Analytiqe, UMR6005 CNRS, Université d'Orléans, 45067 Orléans Cedex 2 (France), Fax: (+33) 2 3841 7281
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  • Dr. Philippe Dauban

    Corresponding author
    1. Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301 CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette (France), Fax: (+33) 1-6907-7247
    • Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301 CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette (France), Fax: (+33) 1-6907-7247
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Abstract

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Yes, nitrenes did “N,O”! Intermolecular addition of nitrene to enecarbamates and enesulfonamides gives oxyamidated products in excellent yields of up to 98 % and with good levels of stereoselectivity. Complete regioselectivity is also observed, leading to the formation of N,O-acetals which can further react with various nucleophiles under acidic conditions (see scheme; TcesNH2=trichloroethylsulfamate).

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