Simple Diastereoselectivity of the BF3·OEt2-Catalyzed Vinylogous Mukaiyama Aldol Reaction of 2-(Trimethylsiloxy)furans with Aldehydes

Carlos Silva López, Rosana Álvarez, Belén Vaz, Olalla Nieto Faza, and Ángel R. de Lera*
Departamento de Qumica Orgnica, Universidade de Vigo, Lagoas-Marcosende, 36310 Vigo, Galicia, Spain
J. Org. Chem., 2005, 70 (9), pp 3654–3659
DOI: 10.1021/jo0501339
Publication Date (Web): March 29, 2005
Copyright © 2005 American Chemical Society
*

 To whom correspondence should be addressed. Fax:  34986812556.

, qolera@uvigo.es

Abstract

Abstract Image

A comprehensive scan of the transition state space for the reaction of 2-(trimethylsiloxy)furan and methacrolein (24 combinations) offered a satisfactory explanation of the high like diastereoselectivity obtained experimentally in the Mukaiyama vinylogous aldol reaction of these and related partners. It was determined that the syn-γ-hydroxyalkylbutenolides are formed preferentially following a g+ orientation of the two reactants with the aldehyde in the s-trans conformation. Diastereoselectivity is shown to be caused by a combination of subtle effects favoring the formation of the like product.

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History

  • Published In Issue April 29, 2005
  • Received January 21, 2005

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