Abstract
Two kinds of N-substituted maleimides bearing L-leucine ester derivatives ((S)-RLMI), i.e. (S)-N-maleoyl-L-leucine methyl ester ((S)-MLMI) and (S)-N-maleoyl-L-leucine benzyl ester ((S)-BnLMI), were synthesized from maleic anhydride, L-leucine, and corresponding alcohols. Asymmetric polymerizations were carried out to obtain optically active polymers. Specific rotations of the poly (RLMI)s were influenced by N-substituents, initiators, solvents and temperature. Chiroptical properties and structures of the poly((S)-RLMI)s obtained were investigated by GPC, CD, and NMR measurements. Optical activities of the poly((S)-RLMI)s obtained with anionic polymerization were attributed to excessive chiral centers of the main chain induced through the polymerizations in addition to the chirality of the N-substituents. The chiral stationary phases (CSPs) for high performance liquid chromatography (HPLC) were prepared and the chiral recognition abilities of the optically active poly((S)-RLMI)s were also discussed.
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Oishi, T., Gao, H., Nakamura, T. et al. Asymmetric Polymerizations of N-Substituted Maleimides Bearing L-Leucine Ester Derivatives and Chiral Recognition Abilities of Their Polymers. Polym J 39, 1047–1059 (2007). https://doi.org/10.1295/polymj.PJ2007022
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DOI: https://doi.org/10.1295/polymj.PJ2007022
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