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    Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.

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    Type
    Article
    Authors
    Mei, Guang-Jian
    Zheng, Wenrui
    Goncalves, Theo
    Tang, Xiwen
    Huang, Kuo-Wei cc
    Lu, Yixin
    KAUST Department
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2020-01-31
    Online Publication Date
    2020-01-31
    Print Publication Date
    2020-02
    Submitted Date
    2019-12-30
    Permanent link to this record
    http://hdl.handle.net/10754/661577
    
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    Abstract
    Chiral phosphoric acid-catalyzed highly enantioselective formal [3 + 2] cycloaddition reaction of azoalkenes with 3-vinylindoles has been established. Under mild conditions, the projected cycloaddition proceeded smoothly, affording a variety of 2,3-dihydropyrroles in high yields and excellent enantioselectivities, and also in a diastereospecific manner. As opposed to the common 4-atom synthons in the previous literature reports, azoalkenes served as 3-atom synthons. Besides, the observed selectivity was supported by primary theoretical calculation. The unique chemistry of azoalkenes disclosed herein will empower asymmetric synthesis of nitrogen-containing ring structural motifs in a broader context.
    Citation
    Mei, G.-J., Zheng, W., Gonçalves, T. P., Tang, X., Huang, K.-W., & Lu, Y. (2020). Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles. iScience, 100873. doi:10.1016/j.isci.2020.100873
    Sponsors
    Y.L. thanks the Singapore National Research Foundation, Prime Minister’s Office for the NRF Investigatorship Award (R-143-000-A15-281). Financial supports from the National University of Singapore (R-143-000-695-114 & C-141-000-092-001) and the National Natural Science Foundation of China (21672158 & 21702077) are also gratefully acknowledged.
    Publisher
    Elsevier BV
    Journal
    iScience
    DOI
    10.1016/j.isci.2020.100873
    Additional Links
    https://linkinghub.elsevier.com/retrieve/pii/S2589004220300572
    http://www.cell.com/article/S2589004220300572/pdf
    Relations
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    • [Dataset]
      Mei, Guang-Jian, Zheng, Wenrui, Gonçalves, Théo P., Tang, Xiwen, Huang, Kuo-Wei, & Lu, Yixin. (2020). CCDC 1957145: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC23PKQ3. DOI: 10.5517/ccdc.csd.cc23pkq3 Handle: 10754/664854
    ae974a485f413a2113503eed53cd6c53
    10.1016/j.isci.2020.100873
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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