A Highly Enantioselective Catalytic Intramolecular Stetter Reaction

Mark S. Kerr, Javier Read de Alaniz, and Tomislav Rovis*
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523
J. Am. Chem. Soc., 2002, 124 (35), pp 10298–10299
DOI: 10.1021/ja027411v
Publication Date (Web): August 10, 2002
Copyright © 2002 American Chemical Society
*

 To whom correspondence should be addressed. E-mail:  rovis@lamar.colostate.edu.

Abstract

Abstract Image

A family of chiral triazolium salts has been developed for inducing the asymmetric intramolecular Stetter reaction. The use of an aminoindanol-derived catalyst affords optimal results, with the product keto esters formed in 82−97% ee and very good chemical yield. Aromatic and aliphatic aldehydes are equally competent substrates for this reaction. The reaction conditions are reasonably mild and allow the isolation of the newly formed stereocenter without epimerization, although the presumed carbenic intermediates are strong bases.

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History

  • Published In Issue September 04, 2002
  • Received June 21, 2002

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