Highly Selective Reaction of α-Halo-α,β-unsaturated Esters with Ketones or Aldehydes Promoted by SmI2:  An Efficient Alternative Access to Baylis−Hillman Adducts

José M. Concellón* and Mónica Huerta
Departamento de Qumica Orgnica e Inorgnica, Facultad de Qumica, Universidad de Oviedo, C/Julin Clavera 8, 33071 Oviedo, Spain
J. Org. Chem., 2005, 70 (12), pp 4714–4719
DOI: 10.1021/jo0504969
Publication Date (Web): May 6, 2005
Copyright © 2005 American Chemical Society
*

 Address correspondence to this author. Fax:  +349853446. Phone:  +34985103457.

, jmcg@fq.uniovi.es

Abstract

Abstract Image

A samarium diiodide promoted addition of aromatic or aliphatic β-substituted-α-halo-α,β-unsaturated esters 1 or 3 to both ketones (in THF) and aldehydes (in acetonitrile) led to (Z)-2-(1-hydroxyalkyl)-2,3-alkenoates 2 and 4 in good yields and very high stereoselectivity. This method constitutes an efficient and valuable alternative to the synthesis of Baylis−Hillman adducts. A mechanism is proposed to explain this transformation.

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History

  • Published In Issue June 10, 2005
  • Received March 11, 2005

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