Highly Enantioselective Azadiene Diels−Alder Reactions Catalyzed by Chiral N-Heterocyclic Carbenes

Ming He, Justin R. Struble, and Jeffrey W. Bode*
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106-9510
J. Am. Chem. Soc., 2006, 128 (26), pp 8418–8420
DOI: 10.1021/ja062707c
Publication Date (Web): June 9, 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.

, bode@chem.ucsb.edu

Abstract

Abstract Image

Highly enantioselective, N-heterocyclic carbene (NHC)-catalyzed aza-Diels−Alder reactions are described. A novel chiral triazolium salt based on the cis-1,2-aminoindanol platform serves as an efficient precatalyst for the NHC-catalyzed redox generation of enolate dienophiles that undergo LUMOdiene-controlled Diels−Alder reactions with N-sulfonyl-α,β-unsaturated imines in good yields and with exceptional diastereo- and enantioselectivities (>99% ee). In contrast to uncatalyzed variants, this organocatalytic process proceeds at room temperature without stoichiometric reagents, producing synthetically valuable, enantiomerically pure cis-3,4-disubstituted dihydropyridinone products.

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History

  • Published In Issue July 05, 2006
  • Received April 18, 2006

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