Catalytic Addition of Metallo-Aldehyde Enolates to Ketones: A New C−C Bond-Forming Hydrogenation
- 30 January 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (5), 691-694
- https://doi.org/10.1021/ol030136c
Abstract
The first catalytic cross-aldolization of metallo-aldehyde enolates with ketone acceptors is enabled via hydrogenation of keto-enals with cationic rhodium catalysts. These results, in conjunction with prior studies involving the catalytic hydrogen-mediated reductive coupling of enones, dienes, and diynes with carbonyl acceptors, support the feasibility of developing a broad new class of catalytic C−C bond formations based on the electrophilic trapping of hydrogenation intermediates.Keywords
This publication has 14 references indexed in Scilit:
- A New Catalytic C-C Bond‐Forming Hydrogenation: Reductive Coupling of Dienes and Glyoxals under Catalytic Hydrogenation ConditionsAngewandte Chemie International Edition, 2003
- First Catalytic Reductive Coupling of 1,3-Diynes to Carbonyl Partners: A New Regio- and Enantioselective C−C Bond Forming HydrogenationJournal of the American Chemical Society, 2003
- Direct Catalytic Asymmetric Enolexo AldolizationsAngewandte Chemie International Edition, 2003
- The Direct Catalytic Asymmetric Cross‐Aldol Reaction of AldehydesAngewandte Chemie International Edition, 2003
- Reaction of Titanate-Type Aldehyde Enolate with Ketones To Provide 3-HydroxyaldehydesJournal of the American Chemical Society, 1999
- The Aldol Reaction: Acid and General Base CatalysisPublished by Elsevier ,1991
- Heterolytic Activation of Hydrogen by Transition Metal ComplexesProgress in Inorganic Chemistry, 1981
- Acyclic stereoselection. 7. Stereoselective synthesis of 2-alkyl-3-hydroxy carbonyl compounds by aldol condensationThe Journal of Organic Chemistry, 1980
- Tris(dialkylamino)sulfonium enolatesJournal of the American Chemical Society, 1980
- Catalytic hydrogenation using cationic rhodium complexes. I. Evolution of the catalytic system and the hydrogenation of olefinsJournal of the American Chemical Society, 1976