The First Cyclopropanation Reaction of Unmasked α,β-Unsaturated Carboxylic Acids:  Direct and Complete Stereospecific Synthesis of Cyclopropanecarboxylic Acids Promoted by Sm/CHI3

José M. Concellón,* Humberto Rodríguez-Solla, and Carmen Simal
Departamento de Qumica Orgnica e Inorgnica, Universidad de Oviedo, Julin Clavera 8, 33071 Oviedo, Spain
Org. Lett., 2007, 9 (14), pp 2685–2688
DOI: 10.1021/ol0709174
Publication Date (Web): June 19, 2007
Copyright © 2007 American Chemical Society

 This paper is dedicated with best wishes to Professor Vincente Gotor on the occasion of his 60th birthday.

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*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jmcg@uniovi.es

Abstract

Abstract Image

A samarium-promoted cyclopropanation of unmasked α,β-unsaturated acids is described. This reaction can be carried out on (E)- or (Z)-α,β-unsaturated carboxylic acids. In all cases the process is completely stereospecific and stereoselective. A mechanism has been proposed to explain the cyclopropanation reaction.

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History

  • Published In Issue July 05, 2007
  • Received April 19, 2007

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