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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: gcfmit.edu

C. Fischer, S. W. Smith, D. A. Powell, G. C. Fu, J. Am. Chem. Soc., 2006, 128, 1472-1473.

DOI: 10.1021/ja058222q (free Supporting Information)


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.

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proposed mechanism



Key Words

α,β-unsaturated compounds, cyclopentanes, cyclohexanes, organocatalysis


ID: J48-Y2006-1530