Asymmetric polymerization of 1-(3-pyridyl)dibenzosuberyl methacrylate and chiral recognition by the obtained optically active polymer having single-handed helical conformation

1-(3-Pyridyl)dibenzosuberyl methacrylate was synthesized and polymerized using the complexes of N,N'-diphenylethylenediamine monolithium amide with (+)-1-(2-pyrrolidinylmethyl)pyrrolidine, (+)-2,3-dimethoxy-1,4-bis(dimethylamino)butane, and (-)-sparteine in toluene at -78 degrees C. The polymers obtained by the helix-sense-selective anionic polymerization were highly isotactic and exhibited large dextrorotation based on single-handed helical conformation. Free-radical polymerization in toluene with (iso-PrOCOO)(2) at 40 degrees C and with alpha,alpha'-azobisisobutyronitrile at 60 degrees C gave nearly perfectly isotactic polymers. The optically active polymer exhibited chiral recognition ability toward trans-stilbene oxide and Triiger's base as revealed by chiral adsorption experiments.