SYNTHESIS AND REACTIONS OF A POLY(METHACRYLATE) FROM AN OPTICALLY-ACTIVE AMINO ALCOHOL

Synthesis and radical polymerization of a novel optically active metha crylate, (S)-2-tert-butoxycarbonylamino-3-phenylpropyl methacrylate (M A-F-BOC), were examined. MA-F-BOC was synthesized from methacrylic aci d and N-protected (L)-phenylalaninol. Radical polymerization of MA-F-B OC quantitatively afforded the corresponding polymethacrylate with a r elatively 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 correspond ing optically active polymeric amine quantitatively. (C) 1998 John Wil ey & Sons, Inc.