Synthesis and reactions of a poly(methacrylate) from an optically active amino alcohol

Synthesis and radical polymerization of a novel optically active methacrylate, (S)-2.-tert-butoxycarbonylamino-3-phenylpropyl methacrylate (MA-F-BOC), were examined. MA-F-BOC was synthesized from methacrylic acid and N-protected (L)-phenylalaninol. Radical polymerization of MA-F-BOC quantitatively afforded the corresponding polymethacrylate with a relatively high molecular weight. Radical copolymerizations of MA-F-BOC were carried out with styrene and acrylamide to afford the copolymers. Radical polymerization of MA-F-BOC in the presence of n-butanethiol afforded the oligomers, whose degrees of polymerizations were 3.3-8.0. The BOC group was completely cloven with HBr to afford the corresponding optically active polymeric amine quantitatively.