Enantioselective Michael/Cyclization Reaction Sequence: Scaffold-Inspired Synthesis of Spirooxindoles with Multiple Stereocenters

Authors

  • Dr. Yiming 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, Lanzhou University, Lanzhou 730000 (China)
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    • These authors contributed equally to this work.

  • Dr. Xianxing Jiang,

    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, Lanzhou University, Lanzhou 730000 (China)
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    • These authors contributed equally to this work.

  • Luping Liu,

    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, Lanzhou University, Lanzhou 730000 (China)
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  • Fangfang 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, Lanzhou University, Lanzhou 730000 (China)
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  • Futing 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, Lanzhou University, Lanzhou 730000 (China)
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  • 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, Lanzhou University, Lanzhou 730000 (China)
    2. State Key Laboratory of Chiroscience, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong (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, Lanzhou University, Lanzhou 730000 (China)
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  • We are grateful for the grants from the National Natural Science Foundation of China (nos. 20932003 and 90813012), the Key National S&T Program “Major New Drug Development” of the Ministry of Science and Technology of China (2009ZX09503-017).

Abstract

original image

A-spiro-ing: The title reaction of α-isothiocyanato imides and methyleneindolinones has been realized for the first time using 1 as the catalyst. This newly developed synthetic method provides a simple, efficient, and environmentally friendly way to access, in an enantioselective manner, densely functionalized spirooxindoles having three contiguous stereogenic centers.

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