Chiral Polymers for Resolution of Enantiomers

In 1979, the formation of one-handed helical poly(triphenylmethyl methacrylate) (PTrMA) was found through the helix-sense-selective polymerization of methacrylate using chiral anionic initiators, and the existence of a stable helical polymer without chiral side chains was proved. The chiral polymer exhibited unexpected high chiral recognition of various racemic compounds when used as the chiral packing material (CPM) for HPLC, which was commercialized in 1982 as the first chiral column based on an optically active polymer. This success encouraged us to develop further useful commercial chiral packing materials (CPMs) based oil polysaccharides, cellulose, and amylose. By using these polysaccharide-based CPMs, particularly phenylcarbamate derivatives, nearly 90% of chiral compounds can be resolved not only analytically but also preparatively, and several chiral drugs have been produced using the CPMs. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 1731-1739, 2009