Bioinspired Manganese and Iron Complexes with Tetradentate N Ligands for the Asymmetric Epoxidation of Olefins

Authors

  • Xiaoe Wang,

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

The manganese and iron complexes with the tetradentate N ligand (1R,2R)-N,N'-dimethyl-N,N'-bis(1-methyl-2-benzimidazolylmethyl)cyclohexane-1,2-diamine have been synthesized and characterized. The crystal structure of the manganese complex demonstrates a cis-α configuration. Both the manganese and iron complexes are active catalysts for the asymmetric epoxidation of olefins with H2O2 as an oxidant and acetic acid as an additive. Up to 96 % ee was observed for the epoxidation of α,β-unsaturated ketones at −20 °C.

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