Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids

• Main Authors: Bandar, Jeffrey (Contributor), Ascic, Erhad (Contributor), Buchwald, Stephen Leffler (Contributor)
• Other Authors: Massachusetts Institute of Technology. Department of Chemistry (Contributor)
• Format: Article
• Language: English
• Published: American Chemical Society (ACS), 2018-01-10T15:24:08Z.
• Subjects: Article
• Online Access: Get fulltext

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.
National Institutes of Health (U.S.) (Grant GM46059)
National Institutes of Health (U.S.) (Grant GM112197)