Cyclodextrins in Polymer Synthesis: Enantiodiscrimination in Free-Radical Polymerization of Cyclodextrin-Complexed Racemic N -Methacryloyl-D,L -phenylalanine Methyl Ester

The enantiodiscriminating polymerization of racemic cyclodextrin-complexed N-methacryloylphenylalanine methyl ester is investigated 1 H NMR spectra of the complexes with methylated β-cyclodextrin in D 2 O manifest splittings due to chiral recognition. The different stabilities of the diastereomeric complexes influence the kinetics of the homopolymerization, particularly at 0°C. An enrichment of the residual N-methacryloyl-L-phenylalanine methyl ester of 14% was achieved after 21 h of polymerization.