Short Communication

Highly Regio- and Diastereoselective Oxazol-5-one Addition to Nitrostyrenes

  1. Andrea-Nekane Balaguer1,
  2. Xavier Companyó1,
  3. Teresa Calvet2,
  4. Mercé Font-Bardía2,
  5. Albert Moyano1,
  6. Ramon Rios1,†

Article first published online: 2 DEC 2008

DOI: 10.1002/ejoc.200801005

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2009, Issue 2, pages 199–203, January 2009

Additional Information

How to Cite

Balaguer, A.-N., Companyó, X., Calvet, T., Font-Bardía, M., Moyano, A. and Rios, R. (2009), Highly Regio- and Diastereoselective Oxazol-5-one Addition to Nitrostyrenes. Eur. J. Org. Chem., 2009: 199–203. doi: 10.1002/ejoc.200801005

Author Information

  1. 1

    Departament de Química Orgánica, Universitat de Barcelona, Martí i Franqués 1–11, 08028 Barcelona, Spain, Fax: +34-933397878

  2. 2

    Departament de Cristal·lografia, Mineralogia i Dipòsits Minerals, Universitat de Barcelona, Martí i Franquès s/n, 08028 Barcelona, Spain

  1. †

    Dr. Ramon Rios ICREA researcher at University of Barcelona.

Publication History

  1. Issue published online: 2 JAN 2009
  2. Article first published online: 2 DEC 2008
  3. Manuscript Received: 15 OCT 2008

Funded by

  • Spanish Ministry of Science and Education. Grant Number: AYA2006-15648-C02-01

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Keywords:

  • Diastereoselective catalysis;
  • Organocatalysis;
  • Heterocycles;
  • Michael addition;
  • Nitrostyrenes;
  • N,O-Aminals

Abstract

A convenient and novel oxazol-5-one addition to nitrostyrenes is reported. The reaction is catalyzed by tertiary amines and yields the corresponding adducts with total regio- and diastereoselectivity. The addition exclusively takes place at the C-2 position of oxazol-5-ones, furnishing diastereopure N,O-aminals. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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