Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids.
A new method for the enantioselective reductive coupling of aryl alkenes with activated carboxylic acid derivatives via copper hydride catalysis is described. Dual catalytic cycles are proposed, with a relatively fast enantioselective hydroacylation cycle followed by a slower diastereoselective ketone reduction cycle. Symmetrical aryl carboxyclic anhydrides provide access to enantioenriched α-substituted ketones or alcohols with excellent stereoselectivity and functional group tolerance.
Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Jeffrey S
JS
Bandar
Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Erhad
E
Ascic
Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Stephen L
SL
Buchwald
D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D000812:Anhydrides / Q000138:chemical synthesis / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013343:Styrenes / Q000138:chemical synthesis / Q000737:chemistry
D000438:Alcohols; D000475:Alkenes; D000812:Anhydrides; D002264:Carboxylic Acids; D006571:Heterocyclic Compounds; D007659:Ketones; D013343:Styrenes; D003300:Copper