Platinum(II) Catalyzed Enantioselective Cycloisomerizations of 3-Hydroxylated 1,5-Enynes

Authors

  • Yang Zhang,

    1. Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Centre de Recherche de Gif, 1, av. de la Terrasse, 91198 Gif-sur-Yvette (France)
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  • Hélène Jullien,

    1. Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Centre de Recherche de Gif, 1, av. de la Terrasse, 91198 Gif-sur-Yvette (France)
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  • Dr. Delphine Brissy,

    1. Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Centre de Recherche de Gif, 1, av. de la Terrasse, 91198 Gif-sur-Yvette (France)
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  • Dr. Pascal Retailleau,

    1. Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Centre de Recherche de Gif, 1, av. de la Terrasse, 91198 Gif-sur-Yvette (France)
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  • Dr. Arnaud Voituriez,

    1. Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Centre de Recherche de Gif, 1, av. de la Terrasse, 91198 Gif-sur-Yvette (France)
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  • Dr. Angela Marinetti

    Corresponding author
    1. Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Centre de Recherche de Gif, 1, av. de la Terrasse, 91198 Gif-sur-Yvette (France)
    • Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Centre de Recherche de Gif, 1, av. de la Terrasse, 91198 Gif-sur-Yvette (France)

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Abstract

The enantioselective cycloisomerization of 3-hydroxylated 1,5-enynes into bicyclo[3.1.0]hexanones was investigated by using cyclometalated NHC-platinum phosphoramidite complexes as pre-catalysts. Several new complexes were prepared. They generate cationic, electrophilic PtII species that efficiently promote the cycloisomerization process. Enantiomeric excesses up to 81 % were obtained in the reactions of enynes with aryl-substituted alkyne functions (8 examples, 70–81 % ee).

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