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Lewis Acid Catalyzed Enlargement of Cyclic β-Alkoxyenals and One-Pot Synthesis of Polyfunctional Enoxysilanes Derived from Aucubin with Trimethylsilyldiazomethane

Authors

  • Dr. Christelle Lemus,

    1. Laboratoire de Pharmacognosie de l'Université Paris - Descartes, Sorbonne Paris Cité, U.M.R./C.N.R.S. n°8638, Faculté des Sciences Pharmaceutiques et Biologiques, 4, Avenue de l'Observatoire, 75006 Paris (France), Fax: (+33) 1-40-46-96-58
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  • Dr. Marko Poleschak,

    1. Laboratoire de Pharmacognosie de l'Université Paris - Descartes, Sorbonne Paris Cité, U.M.R./C.N.R.S. n°8638, Faculté des Sciences Pharmaceutiques et Biologiques, 4, Avenue de l'Observatoire, 75006 Paris (France), Fax: (+33) 1-40-46-96-58
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  • Sophie Gailly,

    1. Laboratoire de Pharmacognosie de l'Université Paris - Descartes, Sorbonne Paris Cité, U.M.R./C.N.R.S. n°8638, Faculté des Sciences Pharmaceutiques et Biologiques, 4, Avenue de l'Observatoire, 75006 Paris (France), Fax: (+33) 1-40-46-96-58
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  • Dr. Marine Desage-El Murr,

    1. Laboratoire de Pharmacognosie de l'Université Paris - Descartes, Sorbonne Paris Cité, U.M.R./C.N.R.S. n°8638, Faculté des Sciences Pharmaceutiques et Biologiques, 4, Avenue de l'Observatoire, 75006 Paris (France), Fax: (+33) 1-40-46-96-58
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  • Prof. Michel Koch,

    1. Laboratoire de Pharmacognosie de l'Université Paris - Descartes, Sorbonne Paris Cité, U.M.R./C.N.R.S. n°8638, Faculté des Sciences Pharmaceutiques et Biologiques, 4, Avenue de l'Observatoire, 75006 Paris (France), Fax: (+33) 1-40-46-96-58
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  • Prof. Brigitte Deguin

    Corresponding author
    1. Laboratoire de Pharmacognosie de l'Université Paris - Descartes, Sorbonne Paris Cité, U.M.R./C.N.R.S. n°8638, Faculté des Sciences Pharmaceutiques et Biologiques, 4, Avenue de l'Observatoire, 75006 Paris (France), Fax: (+33) 1-40-46-96-58
    • Laboratoire de Pharmacognosie de l'Université Paris - Descartes, Sorbonne Paris Cité, U.M.R./C.N.R.S. n°8638, Faculté des Sciences Pharmaceutiques et Biologiques, 4, Avenue de l'Observatoire, 75006 Paris (France), Fax: (+33) 1-40-46-96-58
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Abstract

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Pyrane to oxepane in one step: Highly regio- and stereoselective homologations dependent on the nature of carbonyl function and catalysts have been observed during the formation of enoxysilanes (see scheme). Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and AlCl3 were identified as suitable catalysts to promote the homologation and ring-enlargement.

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