Reductive generation of enolates from enones using elemental hydrogen: catalytic C-C bond formation under hydrogenative conditions.
Exposure of enones to elemental hydrogen in the presence of a Rh(I) catalyst enables reductive enolate generation, as evidenced by electrophilic trapping of the enolate by appendant and exogenous aldehyde partners. The significance of these findings resides in the ability to regioselectivity generate and transform transition metal enolates under catalytic conditions that circumvent formation of stoichiometric byproducts.
Jang
Hye-Young
HY
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA.
Huddleston
Ryan R
RR
Krische
Michael J
MJ
D000438:Alcohols / Q000138:chemical synthesis*; D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D003500:Cyclization; D006859:Hydrogen / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D019163:Reducing Agents / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry
D000438:Alcohols; D000447:Aldehydes; D000475:Alkenes; D007659:Ketones; D009942:Organometallic Compounds; D019163:Reducing Agents; D006859:Hydrogen; D012238:Rhodium