Heterohelicenes with Embedded P-Chiral 1H-Phosphindole or Dibenzophosphole Units: Diastereoselective Photochemical Synthesis and Structural Characterization

Authors

  • Keihann Yavari,

    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), Fax: (+33) 1-69077247
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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), Fax: (+33) 1-69077247
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  • Dr. Arnaud Voituriez,

    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), Fax: (+33) 1-69077247
    • Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Centre de Recherche de Gif, 1, av. de la Terrasse, 91198 Gif-sur-Yvette (France), Fax: (+33) 1-69077247
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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), Fax: (+33) 1-69077247
    • Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Centre de Recherche de Gif, 1, av. de la Terrasse, 91198 Gif-sur-Yvette (France), Fax: (+33) 1-69077247
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Abstract

The oxidative photocyclization reactions of olefins that contain 1H-phosphindole or dibenzophosphole substituents have been applied to the synthesis of P/N-bi-heterosubstituted dimeric helicenes, as well as of new [6]- and [8]phosphahelicenes. In these photocyclization processes, the configuration of the stereogenic phosphorus center dictates the sense of helical chirality. Thus, by starting from enantiomerically pure P-menthylphosphole-oxide units, this method affords enantiopure helical compounds. The helical phosphine oxides were characterized by X-ray diffraction. After reduction of the phosphine-oxides, the corresponding helical phosphines have been used as ligands in transition-metal complexes. The X-ray crystal structure of a gold chloride complex of a [6]helicene is reported.

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