Cinchona Alkaloid Amide Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Synthesis of 2,4-Disubstituted Azetidines

Authors

  • Jean-Baptiste Denis,

    1. Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France), Fax: (+33) 1-6907-7247
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  • Dr. Géraldine Masson,

    Corresponding author
    1. Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France), Fax: (+33) 1-6907-7247
    • Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France), Fax: (+33) 1-6907-7247
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  • Dr. Pascal Retailleau,

    1. Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France), Fax: (+33) 1-6907-7247
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  • Prof. Dr. Jieping Zhu

    Corresponding author
    1. Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France), Fax: (+33) 1-6907-7247
    2. Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), EPFL-SB-ISIC-LSPN, 1015 Lausanne (Switzerland), Fax: (+41) 21-693-9740
    • Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France), Fax: (+33) 1-6907-7247
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  • Financial supports from CNRS and ICSN are gratefully acknowledged. J.B.D. thanks ANR for a doctoral fellowship.

Abstract

original image

Mix and go: The quinidine amide 1 catalyzed [2+2] cycloaddition between N-sulfonylimines 2 and alkyl 2,3-butadienoates 3 afforded the R-configured azetidines 4 in excellent yields and enantioselectivities (M.S.=molecular sieve). The S enantiomer was obtained when a quinine amide catalyst, the pseudoenantiomer of 1, was used.

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