Umpolung of Michael Acceptors Catalyzed by N-Heterocyclic Carbenes

Christian Fischer, Sean W. Smith, David A. Powell, and Gregory C. Fu*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
J. Am. Chem. Soc., 2006, 128 (5), pp 1472–1473
DOI: 10.1021/ja058222q
Publication Date (Web): January 17, 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.

, gcf@mit.edu

Abstract

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N-Heterocyclic carbenes can catalyze β-alkylations of a range of α,β-unsaturated esters, amides, and nitriles that bear pendant leaving groups to form a variety of ring sizes. In this process, the nucleophilic catalyst transiently transforms the normally electrophilic β carbon into a nucleophilic site through an unanticipated addition−tautomerization sequence.

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History

  • Published In Issue February 08, 2006
  • Received December 3, 2005

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