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Synthesis 2018; 50(20): 4104-4112
DOI: 10.1055/s-0037-1610540
paper
© Georg Thieme Verlag Stuttgart · New York

Isocyanide-Based MCRs: Straightforward Access to Perfluroalkyl­ated γ-Spiroiminolactones

Authors

  • Lili Tao

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn

  • Zhenhua Fan

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn

  • Xin Peng

    b   Qianweichang College, Shanghai University, Shanghai 200444, P. R. of China

  • Jing Han

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn

  • Weimin He

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn

  • Jie Chen

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn

  • Hongmei Deng

    c   Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai 200444, P. R. of China

  • Min Shao

    c   Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai 200444, P. R. of China

  • Hui Zhang*

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
    c   Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai 200444, P. R. of China

  • Weiguo Cao*

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
    d   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of S ciences, Shanghai 200032, P. R. of China
    e   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

The authors are grateful to the National Natural Science Foundation of China (NSFC) (Grant Nos. 21672138, 21542005, 21272152) for financial support.
Further Information

Publication History

Received: 07 May 2018

Accepted after revision: 06 June 2018

Publication Date:
16 July 2018 (online)

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Graphical Abstract

Abstract

A variety of perfluoroalkyl-substituted γ-spiroiminolactones have been synthesized via a one-pot, three-component cascade reaction in which isocyanides, methyl perfluoroalk-2-ynoates and 1,2-diketones undergo highly regioselective Michael addition, nucleophilic addition and cyclization. This reaction has the advantages of good to excellent chemical yields, operationally simple procedure, and short reaction times.

Key words

spiroiminolactones - perfluoroalkyl-substituted - isocyanide - multicomponent reaction - methyl perfluoroalk-2-ynoate

Supporting Information