Catalytic Addition of Metallo-Aldehyde Enolates to Ketones:  A New C−C Bond-Forming Hydrogenation

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 d...

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Bibliographic Details
Published in:Organic letters 2004-03, Vol.6 (5), p.691-694
Main Authors: Koech, Phillip K, Krische, Michael J
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Aldehydes - chemistry
Catalysis
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Hydrogenation
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Oxidation-Reduction
Rhodium - chemistry
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol030136c