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Silylated Vinyloxiranes – Recent Advances and Synthetic Applications

  1. Frédéric Marion,
  2. Sandrine Calvet,
  3. Jean-Charles Marié,
  4. Christine Courillon,
  5. Max Malacria

Article first published online: 17 NOV 2005

DOI: 10.1002/ejoc.200500578

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2006, Issue 2, pages 453–462, January 2006

Additional Information

How to Cite

Marion, F., Calvet, S., Marié, J.-C., Courillon, C. and Malacria, M. (2006), Silylated Vinyloxiranes – Recent Advances and Synthetic Applications. Eur. J. Org. Chem., 2006: 453–462. doi: 10.1002/ejoc.200500578

Author Information

  1. Université Pierre et Marie Curie, Laboratoire de Chimie Organique, associé au CNRS, FR 2769, 4 place jussieu, 75252 Paris cedex 05, France, Fax: +33-1-4427-7360

Publication History

  1. Issue published online: 2 JAN 2006
  2. Article first published online: 17 NOV 2005
  3. Manuscript Received: 29 JUL 2005

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Keywords:

  • Aldehydes;
  • Lactones;
  • Michael addition;
  • Palladium;
  • Rearrangement

Abstract

Stereoselective preparation of α-silylated α-quaternary unsaturated aldehydes 2 from variously substituted silylated vinyloxiranes is achieved with the aid of palladium(0) catalysis under smooth experimental conditions. One example of a versatile application of this rearrangement reaction, in the case of the tert-butyldimethyl(3-vinyloxiran-2-yl)silane derivative 1a, has resulted in one-pot diastereoselective syntheses of the highly functionalized polysubstituted δ-lactones 33–39, the reactivity of which has been studied.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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