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Synfacts 2005(3): 0347-0347  
DOI: 10.1055/s-2005-921650
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Asymmetric Reductive Michael Cyclization of Enal Enones

Contributor(s): Benjamin List, Nolwenn J. A. Martin
J. W. Yang, M. T. Hechavarria Fonseca, B. List*
Max-Planck-Institut für Kohlenforschung, Mühlheim/Ruhr, Germany
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

A highly enantioselective organocatalytic reductive Michael cyclization of enal enones is described. This tandem reaction is mediated by a single imidazolidinone organocatalyst in the presence of a commercially available ­Hantzsch ester under simple and mild conditions to provide cyclic keto aldehydes in high yields and enantioselectivities. The reaction sequence works well with aliphatic and aromatic substrates in the synthesis of five- and six-membered carbacyclic derivatives.