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, Email: gcf
mit.edu
C. Fischer, S. W. Smith, D. A. Powell, G. C. Fu, J. Am. Chem. Soc., 2006, 128, 1472-1473.
DOI: 10.1021/ja058222q
Abstract
N-heterocyclic carbenes catalyze intramolecular β-alkylations of α,β-unsaturated esters, amides, and nitriles that bear pendant leaving groups to form a variety of ring sizes. The mechanism is discussed.
see article for more examples
proposed mechanism
Key Words
α,β-unsaturated compounds, cyclopentanes, cyclohexanes, organocatalysis
ID: J48-Y2006-1530
