Organocatalytic Michael Cycloisomerization of Bis(enones): The Intramolecular Rauhut−Currier Reaction
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- 26 February 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (11) , 2402-2403
- https://doi.org/10.1021/ja0121686
Abstract
The utilization of enones as latent enolates enables regioselective enolate formation from chemically robust presursors. In this communication, we report a catalytic Michael cycloisomerization of bis(enones) under Morita−Baylis−Hillman conditions. Upon exposure to 10 mol % tributylphosphine, bis(enone) substrates afford both five- and six-membered ring products. Notably, unsymmetrical bis(enones) possessing sufficient steric or electronic bias yield single isomeric products.Keywords
This publication has 7 references indexed in Scilit:
- Catalytic Dimerization of Alkyl Acrylates∗Catalysis Reviews, 1996
- Syntheses of Polycyclic Natural Products Employing the Intramolecular Double Michael ReactionAngewandte Chemie International Edition in English, 1993
- An intramolecular Baylis-Hillman reactionTetrahedron Letters, 1992
- Synthetic potential of the tertiary-amine-catalysed reaction of activated vinyl carbanions with aldehydesTetrahedron, 1988
- Novel synthesis of β-siloxy esters by condensation of carbonyls and trimethylsilane with α,β-unsaturated esters catalyzed by RhCl3Tetrahedron Letters, 1987
- Alkylation and Carbonation of Ketones by Trapping the Enolates from the Reduction of α,β-Unsaturated KetonesJournal of the American Chemical Society, 1965
- THE α-ALKYLATION OF ENOLATES FROM THE LITHIUM-AMMONIA REDUCTION OF α,β-UNSATURATED KETONESJournal of the American Chemical Society, 1961