Benzyl and phenylthiomethyl silanes: A new class of bifunctional linchpins for type II anion relay chemistry (ARC)

Abstract

"Chemical Equation Presented" 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 (R 1), while diastereomeric mixtures were obtained when a phenylthiol moiety served as the ASG, irrespective of α-substitution. © 2010 American Chemical Society.