A Transient Directing Group Strategy Enables Enantioselective Reductive Heck Hydroarylation of Alkenes

Abstract

<p>Metal-coordinating directing groups have seen extensive use in the field of transition-metal-mediated functionalization of alkenes; however, their waste-generating installation and removal steps limit the efficiency and practicality of reactions that rely on their use. Inspired by developments in the field of C–H activation, herein we report a transient directing group approach to reductive Heck hydroarylation of alkenyl benzaldehyde substrates that proceeds under mild conditions. Highly stereoselective migratory insertion is facilitated by in situ formation of an imine from catalytic amounts of commercially available amino acid additive. Computational studies reveal an unusual mode of enantioinduction by the remote chiral center in the transient directing group.</p>