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synthesis of main-chain chiral quaternary ammonium polymers for asymmetric catalysis using quaternization polymerization对不对称催化合成主链聚合物手性季铵使用碱化反应聚合.pdf

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Molecules 2012, 17, 7569-7583; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis of Main-Chain Chiral Quaternary Ammonium Polymers for Asymmetric Catalysis Using Quaternization Polymerization Naoki Haraguchi *, Parbhej Ahamed, Md. Masud Parvez and Shinichi Itsuno Department of Environmental and Life Sciences, Graduate School of Engineering, Toyohashi University of Technology, 1-1 Hibarigaoka, Tenpaku-cho, Toyohashi, Aichi 441-8580, Japan * Author to whom correspondence should be addressed; E-Mail: haraguchi@ens.tut.ac.jp; Tel.: +81-532-44-6812; Fax: +81-532-48-5833. Received: 27 April 2012; in revised form: 4 June 2012 / Accepted: 13 June 2012 / Published: 19 June 2012 Abstract: Main-chain chiral quaternary ammonium polymers were successfully synthesized by the quaternization polymerization of cinchonidine dimer with dihalides. The polymerization occurred smoothly under optimized conditions to give novel type of main-chain chiral quaternary ammonium polymers. The catalytic activity of the polymeric chiral organocatalysts was investigated on the asymmetric benzylation of N-(diphenylmethylidene)glycine tert-butyl ester. Keywords: chiral polymer; quaternization polymerization; organocatalysis; cinchona alkaloid; quaternary ammonium salt 1. Introduction Cinchona alkaloids are among the most attractive chiral molecules because they represent readily available and inexpensive

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