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Manganese Catalysts with C1-Symmetric N4 Ligand for Enantioselective Epoxidation of Olefins

Authors

  • Bin Wang,

    1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000 (P.R. China), Fax: (+86) 931-827-7088
    2. Graduate School of the Chinese Academy of Sciences, Beijing, 100039 (P.R. China)
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  • Dr. Chengxia Miao,

    1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000 (P.R. China), Fax: (+86) 931-827-7088
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  • Shoufeng Wang,

    1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000 (P.R. China), Fax: (+86) 931-827-7088
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  • Prof. Dr. Chungu Xia,

    1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000 (P.R. China), Fax: (+86) 931-827-7088
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  • Prof. Dr. Wei Sun

    Corresponding author
    1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000 (P.R. China), Fax: (+86) 931-827-7088
    • State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000 (P.R. China), Fax: (+86) 931-827-7088
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Abstract

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Bioinspired manganese complexes based on N4 ligands, with a more rigid, chiral diamine derived from proline and two benzimidazoles, were synthesized and applied to epoxidize olefins with hydrogen peroxide as a clean oxidant. Notably, 60–99 % isolated yields and excellent ee values (up to 95 %) were obtained by using low catalyst loadings (0.01–0.2 mol %; see scheme; F green, S yellow).

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