Preparation of Chiral Ligands Connected with Quaternary Ammonium Group for Recyclable Catalytic Asymmetric Transfer Hydrogenation in Ionic Liquid

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  • Uchimoto Hitomi
    School of Pharmaceutical Sciences, Mukogawa Women’s University
  • Tsuji Tomoko
    Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University
  • Kawasaki Ikuo
    School of Pharmaceutical Sciences, Mukogawa Women’s University Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University
  • Arimitsu Kenji
    School of Pharmaceutical Sciences, Mukogawa Women’s University
  • Yasui Hiroyuki
    Department of Analytical and Bioinorganic Chemistry, Division of Analytical and Physical Sciences, Kyoto Pharmaceutical University
  • Yamashita Masayuki
    Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University
  • Ohta Shunsaku
    Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University
  • Nishide Kiyoharu
    School of Pharmaceutical Sciences, Mukogawa Women’s University

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Reuse of chiral ruthenium catalyst in catalytic asymmetric transfer hydrogenation (CATH) has attracted attention from economic and environmental viewpoints, and reactions using ionic liquids (ILs) as solvent are recognized as one of the most useful methods for reuse of the catalyst. We synthesized (1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (TsDPEN) derivatives with various ionic moieties, and investigated the effect of their structure with respect to catalytic ability and recyclability in CATH with ILs. Ligand 3a having an imidazolium group showed the best results, and significant differences were observed depending on the structure of the ionic moiety or the length of the alkyl chain connecting the ligand site and the ionic moiety. Among various prochiral ketones used as substrates at various cycles, 3a showed a relatively good result.

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