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Synfacts 2006(11): 1177-1177
DOI: 10.1055/s-2006-949457
DOI: 10.1055/s-2006-949457
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Organocatalytic Transfer Hydrogenation of Cyclic Enones
J. B. Tuttle, S. G. Ouellet, D. W. C. MacMillan*
California Institute of Technology, Pasadena, USA
Further Information
Publication History
Publication Date:
24 October 2006 (online)

Significance
The authors describe a highly enantioselective organocatalytic transfer hydrogenation of cyclic α,β-unsaturated ketones 1. The reaction is mediated by imidazolidinone catalyst 3, which has previously been used in iminium catalytic Diels-Alder reactions of α,β-unsaturated ketones with dienes. Valuable chiral cyclic ketones 4 are obtained in moderate to good yields and good to excellent enantioselectivities in the presence of tert-butyl Hantzsch ester 2 as hydrogen source. This process was successfully applied to five-, six-, and seven-membered ring systems.