Construction of Si‐Stereogenic Silanols by Palladium‐Catalyzed Enantioselective C−H Alkenylation

Abstract

AbstractThe construction of silicon‐stereogenic silanols via Pd‐catalyzed intermolecular C−H alkenylation with the assistance of a commercially available L‐pyroglutamic acid has been realized for the first time. Employing oxime ether as the directing group, silicon‐stereogenic silanol derivatives could be readily prepared with excellent enantioselectivities, featuring a broad substrate scope and good functional group tolerance. Moreover, parallel kinetic resolution with unsymmetric substrates further highlighted the generality of this protocol. Mechanistic studies indicate that L‐pyroglutamic acid could stabilize the Pd catalyst and provide excellent chiral induction. Preliminary computational studies unveil the origin of the enantioselectivity in the C−H bond activation step.