Catalytic Enantioselective Ring-Opening Reaction of meso-Aziridines with α-Isothiocyanato Imides

Authors

  • Yi-Ming Cao,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu, Province, State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, School of Life Science, Lanzhou University, Lanzhou 730000 (P. R. China)
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  • Fu-Ting Zhang,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu, Province, State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, School of Life Science, Lanzhou University, Lanzhou 730000 (P. R. China)
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    • These two authors contributed equally to this work.

  • Fang-Fang Shen,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu, Province, State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, School of Life Science, Lanzhou University, Lanzhou 730000 (P. R. China)
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    • These two authors contributed equally to this work.

  • Prof. Dr. Rui Wang

    Corresponding author
    1. Key Laboratory of Preclinical Study for New Drugs of Gansu, Province, State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, School of Life Science, Lanzhou University, Lanzhou 730000 (P. R. China)
    2. State Key Laboratory of Chiroscience, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong (P. R. China)
    • Key Laboratory of Preclinical Study for New Drugs of Gansu, Province, State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, School of Life Science, Lanzhou University, Lanzhou 730000 (P. R. China)

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Abstract

original image

Open up your chemistry! By using cinchonine-based trimeric quaternary ammonium salts as catalysts, meso-aziridines can be ring-opened, in an enantioselective manner, through nucleophilic addition of the sulfur atom of α-isothiocyanato imides (see scheme; PG=protecting group). This synthetic method provides an efficient way to access useful chiral β-aminothiooxazole compounds.

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