Complex Bioactive Alkaloid-Type Polycycles through Efficient Catalytic Asymmetric Multicomponent Aza-Diels–Alder Reaction of Indoles with Oxetane as Directing Group

Authors

  • Zhilong Chen,

    1. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China)
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  • Beilei Wang,

    1. Department of Biology and Chemistry, City University of Hong Kong, Kowloon Tong, Hong Kong SAR (China)
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  • Zhaobin Wang,

    1. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China)
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  • Prof. Dr. Guangyu Zhu,

    Corresponding author
    1. Department of Biology and Chemistry, City University of Hong Kong, Kowloon Tong, Hong Kong SAR (China)
    • Department of Biology and Chemistry, City University of Hong Kong, Kowloon Tong, Hong Kong SAR (China)
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  • Prof. Dr. Jianwei Sun

    Corresponding author
    1. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China)
    • Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China)
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  • Financial support was provided by HKUST, City University of Hong Kong (7002759), and Hong Kong RGC (HKUST604411). We thank Prof. Hongkai Wu for sharing equipment. We also thank Dr. H. H.-Y. Sung and Prof. I. Williams for their assistance with the structure determination.

Abstract

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Starting from three achiral compounds, the title reaction provides rapid access to a variety of molecules that contain indoline, tetrahydroquinoline, and tetrahydroisoquinoline moieties (see scheme). The process features the efficient formation of multiple new bonds and chiral centers, excellent stereoselectivity, oxetane desymmetrization, and easy product purification through filtration.

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