Aldol-type Reactions of Unmasked Iodoacetic Acid with Carbonyl Compounds Promoted by Samarium Diiodide:  Efficient Synthesis of Carboxylic 3-Hydroxyacids and Their Derivatives

José M. Concellón* and Carmen Concellón
Departamento de Qumica Orgnica e Inorgnica, Facultad de Qumica, Universidad de Oviedo, Julin Clavera 8, 33071 Oviedo, Spain
J. Org. Chem., 2006, 71 (12), pp 4428–4432
DOI: 10.1021/jo060118j
Publication Date (Web): May 10, 2006
Copyright © 2006 American Chemical Society
*

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

An easy, direct, general, and efficient samarium diiodide-mediated preparation of 3-hydroxyacids 1 in high yield by reaction of different aldehydes or ketones with commercially available iodoacetic acid is described. The application of different esterification procedures to the crude 3-hydroxyacids so obtained afforded the corresponding 3-hydroxyesters. Also, the cyclization of crude 3-hydroxycarboxylic acids allowed the preparation of β-lactones. A mechanism is proposed to explain the synthesis of 3-hydroxyacids 1.

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History

  • Published In Issue June 09, 2006
  • Received January 19, 2006

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