Benzyl and Phenylthiomethyl Silanes: A New Class of Bifunctional Linchpins for Type II Anion Relay Chemistry (ARC)

A new class of bifunctional linchpins bearing electrophilic sites β or γ to a silyl group have been designed, synthesized, and demonstrated to be competent in tricomponent unions exploiting Type II Anion Relay Chemistry (ARC). High diastereoselectivities were observed when a phenyl moiety (R2) served as an anion-stabilizing group (ASG) adjacent to a methyl susbtituent (R1), while diastereomeric mixtures were obtained when a phenylthiol moiety served as the ASG, irrespective of α-substitution.