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 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. [reaction: see text]
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712, USA.
Phillip K
PK
Koech
Michael J
MJ
Krische
D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D006865:Hydrogenation; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D000447:Aldehydes; D006571:Heterocyclic Compounds; D007659:Ketones; C116609:3-hydroxybutanal; D012238:Rhodium