Diastereoselective synthesis of β-hydroxy allylic tertiary sulfides via nickel/photoredox cooperative catalysis

Abstract

β-Hydroxy allylic sulfides represent privileged motifs in bioactive molecules but remain challenging to synthesize owing to sulfur-mediated catalyst poisoning and stereocontrol issues. We report a nickel/photoredox cooperative catalysis system for the diastereoselective allylation of aldehydes with sulfur-substituted allylic acetates. Using an organic photocatalyst 4CzIPN under 450 nm blue light at room temperature, this protocol affords diverse β-hydroxy allylic tertiary sulfides in good yields with excellent diastereoselectivities (up to >20 : 1 dr). Broad substrate scope, mild conditions, and good functional group tolerance are demonstrated.