Asymmetric Polymerization of Dialdehyde and Bis(allylsilane) in the Presence of Chiral (Acyloxy)borane Catalyst

Abstract

We present a study of the asymmetric polymerization of dialdehyde and bis(allylsilane) based on the enantioselective addition of allylsilane to aldehyde in the presence of chiral Lewis acid. Chiral (acyloxy)borane (CAB) derived from enantiopure tartaric acid was used as a chiral Lewis acid to promote the asymmetric polymerization. Repetitive allylation reaction between these monomers in the presence of CAB yielded optically active polymers having asymmetric carbons in their main chain. The corresponding model asymmetric reaction of β-substituted allylsilane with benzaldehyde was also studied.