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Highly Enantioselective Reduction of β-Amino Nitroolefins with a Simple N-Sulfinyl Urea as Bifunctional Catalyst

Authors

  • Xiang-Wei Liu,

    1. Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P. R. China), Fax: (+86) 28-85222753
    2. Graduate University of the Chinese Academy of Sciences, Beijing 100049 (P. R. China)
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  • Yan Yan,

    1. Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P. R. China), Fax: (+86) 28-85222753
    2. Graduate University of the Chinese Academy of Sciences, Beijing 100049 (P. R. China)
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  • Yong-Qiang Wang,

    1. Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P. R. China), Fax: (+86) 28-85222753
    2. Graduate University of the Chinese Academy of Sciences, Beijing 100049 (P. R. China)
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  • Chao Wang,

    1. Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P. R. China), Fax: (+86) 28-85222753
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  • Prof. Dr. Jian Sun

    Corresponding author
    1. Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P. R. China), Fax: (+86) 28-85222753
    • Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P. R. China), Fax: (+86) 28-85222753
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Abstract

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Simple but effective: A structurally simple N-sulfinyl urea was found to be a highly efficient bifunctional catalyst, which allows for the development of a novel pathway for the construction of chiral β-amino nitroalkanes through enantioselective reduction of β-amino nitroolefins by trichlorosilane. High yields and excellent enantioselectivities were obtained for a broad range of β-arylamino nitroolefin substrates (see scheme).

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