Enantioselective Heck Arylations of Acyclic Alkenyl Alcohols Using a Redox-Relay Strategy

Abstract

From C=C to C=O The palladium-catalyzed Heck reaction is widely used to form carbon-carbon bonds between aryl rings and olefins, after which elimination of a hydrogen atom restores the olefin's double bond. Werner et al. (p. 1455 ; see the Perspective by Gilbertson ) present a variant of this reaction in which a hydrogen atom is instead lost from an alcohol center elsewhere in the molecule, yielding a ketone and a chiral center where the arene is bound. The process is highly enantioselective and also versatile: The alcohol can be sited one, two, or even three carbons away from the olefin.