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Catalytic Asymmetric Michael Addition/Cyclization of Isothiocyanato Oxindoles: Highly Efficient and Versatile Approach for the Synthesis of 3,2′-Pyrrolidinyl Mono- and Bi-spirooxindole Frameworks

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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  • 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 authors contributed equally to this work

  • 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 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

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A-spiro-ing to greatness: The catalytic asymmetric Michael addition/cyclization of isothiocyanato oxindoles has been realized. This versatile approach provides an easy and highly efficient way to access not only the enantioselective synthesis of 3,2′-pyrrolidinyl spirooxindole frameworks, but also the construction of enatiomerically enriched bi-spirooxindoles containing three contiguous stereocenters and two spiro-quaternary centers (see scheme).

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