Diastereoselective Metal-Catalyzed Synthesis of C-Aryl and C-Vinyl Glycosides

Authors

  • Dr. Lionel Nicolas,

    1. Laboratoire de Chimie Organique, ESPCI ParisTech, UMR CNRS 7084, 10 Rue Vauquelin—75231 Paris Cedex 05 (France)
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  • Dr. Patrick Angibaud,

    1. Janssen Research & Development, Oncology Medicinal Chemistry, Campus de Maigremont—BP615–27106, Val de Reuil Cedex (France)
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  • Dr. Ian Stansfield,

    1. Janssen Research & Development, Oncology Medicinal Chemistry, Campus de Maigremont—BP615–27106, Val de Reuil Cedex (France)
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  • Dr. Pascal Bonnet,

    1. Janssen Research & Development, Janssen Pharmaceutica N.V. Turnhoutsweg 30, 2340 Beerse (Belgium)
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  • Dr. Lieven Meerpoel,

    1. Janssen Research & Development, Janssen Pharmaceutica N.V. Turnhoutsweg 30, 2340 Beerse (Belgium)
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  • Dr. Sébastien Reymond,

    Corresponding author
    1. Laboratoire de Chimie Organique, ESPCI ParisTech, UMR CNRS 7084, 10 Rue Vauquelin—75231 Paris Cedex 05 (France)
    • Laboratoire de Chimie Organique, ESPCI ParisTech, UMR CNRS 7084, 10 Rue Vauquelin—75231 Paris Cedex 05 (France)
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  • Prof. Dr. Janine Cossy

    Corresponding author
    1. Laboratoire de Chimie Organique, ESPCI ParisTech, UMR CNRS 7084, 10 Rue Vauquelin—75231 Paris Cedex 05 (France)
    • Laboratoire de Chimie Organique, ESPCI ParisTech, UMR CNRS 7084, 10 Rue Vauquelin—75231 Paris Cedex 05 (France)
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  • Janssen Research & Development (grant to L.N.) is gratefully acknowledged.

Abstract

original image

Cobalt, the catalyst of choice: The diastereoselective cobalt-catalyzed cross-coupling of 1-bromo glycosides and aryl or vinyl Grignard reagents is described. A convenient and inexpensive catalyst, [Co(acac)3]/tmeda (acac=acetylacetonate, tmeda=N,N′-tetramethylethylenediamine), gives full α selectivity in the mannose and galactose series, and an α selectivity in the glucose series with α/β ratios of 1.3:1–3:1.

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