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Published October 4, 2006 | Supplemental Material
Journal Article Open

Organocatalytic Transfer Hydrogenation of Cyclic Enones

Abstract

The first enantioselective organocatalytic transfer hydrogenation of cyclic enones has been accomplished. The use of iminium catalysis has provided a new organocatalytic strategy for the enantioselective reduction of β,β-substituted α,β-unsaturated cycloalkenones, to generate β-stereogenic cyclic ketones. The use of imidazolidinone 4 as the asymmetric catalyst has been found to mediate the hydrogenation of a large class of enone substrates with tert-butyl Hantzsch ester serving as an inexpensive source of hydrogen. The capacity of catalyst 4 to enable enantioselective transfer hydrogenation of cycloalkenones has been extended to five-, six-, and seven-membered ring systems. The sense of asymmetric induction is in complete accord with the stereochemical model first reported in conjunction with the use of catalyst 4 for enantioselective ketone Diels−Alder reactions.

Additional Information

© 2006 American Chemical Society. Received July 24, 2006. Publication Date (Web): September 8, 2006. Financial support was provided by the NIHGMS (R01 GM66142-01) and kind gifts from Amgen, Merck, and the Astellas Foundation. S.G.O. is grateful for an NSERC fellowship.

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August 19, 2023
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