Enantioselective Organocatalytic Michael Additions of Aldehydes to Enones with Imidazolidinones: Cocatalyst Effects and Evidence for an Enamine Intermediate
- 21 July 2005
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (33) , 11598-11599
- https://doi.org/10.1021/ja0532584
Abstract
An enantioselective intermolecular Michael addition of aldehydes to enones catalyzed by imidazolidinones has been achieved. Chemoselectivity (Michael addition vs aldol) can be controlled through judicious choice of hydrogen-bond-donating cocatalysts. The optimal imidazolidinone/hydrogen-bond-donor pair affords Michael addition products in excess of 90% ee. Furthermore, we have isolated and characterized an enamine intermediate and demonstrated its efficacy as a nucleophile in the observed Michael addition reactions.Keywords
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