Conversion of α,β-Unsaturated Aldehydes into Saturated Esters: An Umpolung Reaction Catalyzed by Nucleophilic Carbenes

Audrey Chan and Karl A. Scheidt*
Department of Chemistry, Northwestern University, Evanston, Illinois 60208
Org. Lett., 2005, 7 (5), pp 905–908
DOI: 10.1021/ol050100f
Publication Date (Web): February 4, 2005
Copyright © 2005 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.

, scheidt@northwestern.edu

Abstract

Abstract Image

N-Heterocyclic carbenes derived from benzimidazolium salts are effective catalysts for generating homoenolate species from α,β-unsaturated aldehydes. These nucleophilic intermediates can be protonated, and the resulting activated carbonyl unit is trapped with an alcohol nucleophile, thereby promoting a highly efficient conversion of an α,β-unsaturated aldehyde into a saturated ester. A kinetic resolution of secondary alcohols can be achieved using chiral imidazoylidene catalysts.

View: Full Text HTML | Hi-Res PDF

Tools

History

  • Published In Issue March 03, 2005
  • Received January 18, 2005

Recommend & Share

Related Content

Other ACS content by these authors: