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Enantioselective Construction of Spirooxindole Derivatives through [3+2] Annulation Catalyzed by a Bisthiourea as a Multiple-Hydrogen-Bond Donor

Authors

  • Yan Shi,

    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China), Fax: (+86) 25-83594886
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  • Aijun Lin,

    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China), Fax: (+86) 25-83594886
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  • Haibin Mao,

    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China), Fax: (+86) 25-83594886
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  • Zhijie Mao,

    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China), Fax: (+86) 25-83594886
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  • Weipeng Li,

    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China), Fax: (+86) 25-83594886
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  • Prof. Dr. Hongwen Hu,

    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China), Fax: (+86) 25-83594886
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  • Prof. Dr. Chengjian Zhu,

    Corresponding author
    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China), Fax: (+86) 25-83594886
    2. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 (P. R. China)
    • School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China), Fax: (+86) 25-83594886
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  • Prof. Dr. Yixiang Cheng

    Corresponding author
    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China), Fax: (+86) 25-83594886
    • School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China), Fax: (+86) 25-83594886
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Abstract

original image

Anything between ureas? Spiro[isoxazolidine-3,3′-oxindole]s have been constructed by employing methyleneindolinones and nitrones as the starting materials through [3+2] annulation catalyzed by a bisthiourea. Products with three contiguous stereocenters, including one spiroquaternary stereocenter, are obtained in good yields with excellent enantio- and diastereoselectivity. The bisthiourea catalyst acts as a multiple-hydrogen-bond donor to simultaneously activate both substrates.

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