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Synfacts 2006(8): 0840-0840  
DOI: 10.1055/s-2006-942031
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

NHC-Catalyzed Azadiene Diels-Alder Reaction

Contributor(s): Benjamin List, Sebastian Hoffmann
M. He, J. R. Struble, J. W. Bode*
University of California, Santa Barbara, USA
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

The first NHC-catalyzed Diels-­Alder reaction is described in which a reactive dienophile was generated in situ from a carbene and an α,β-unsaturated aldehyde. In the course of the reaction the dienophiles react with α,β-unsaturated aldimines, leading to chiral dihydropyridinone products in high yields and excellent enantio­selectivities. This is a rare example of a highly enantioselective NHC-organocatalyzed intermolecular C-C bond forming reaction.