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Ruthenium-Catalyzed Coupling of Oxabenzonorbornadienes with Alkynes Bearing a Propargylic Oxygen Atom: Access to Stereodefined Benzonorcaradienes

Authors

  • Dr. Alphonse Tenaglia,

    Corresponding author
    1. Equipe Chirosciences-ISM2-UMR CNRS 6263, Université Aix-Marseille III, Av. Escadrille Normandie Niemen, 13397 Marseille cedex 20 (France)
    • Equipe Chirosciences-ISM2-UMR CNRS 6263, Université Aix-Marseille III, Av. Escadrille Normandie Niemen, 13397 Marseille cedex 20 (France)
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  • Sylvain Marc,

    1. Equipe Chirosciences-ISM2-UMR CNRS 6263, Université Aix-Marseille III, Av. Escadrille Normandie Niemen, 13397 Marseille cedex 20 (France)
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  • Laurent Giordano,

    1. Equipe Chirosciences-ISM2-UMR CNRS 6263, Université Aix-Marseille III, Av. Escadrille Normandie Niemen, 13397 Marseille cedex 20 (France)
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  • Innocenzo De Riggi

    1. Equipe Chirosciences-ISM2-UMR CNRS 6263, Université Aix-Marseille III, Av. Escadrille Normandie Niemen, 13397 Marseille cedex 20 (France)
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  • We thank Dr. M. Giorgi (Spectropole, Université Aix-Marseille) for the X-ray analyses. Financial support from CNRS and MESR is gratefully acknowledged.

Abstract

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Stereodefined: The title reaction provides an atom-economic route to benzonorcaradienes. The diastereoselectivity of the coupling relies upon the structure of the alkene; unsubstituted bicyclic alkenes afforded exclusively exo-benzonorcaradienes (see scheme) whereas the bicyclic alkenes with substituents at the bridgehead positions resulted in endo-benzonorcaradienes.

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