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Copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of 1,3-enynes and azomethine ylides

Author

Listed:
  • Bo-Ran Wang

    (Shanghai University of Traditional Chinese Medicine
    University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Yan-Bo Li

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Qi Zhang

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Dingding Gao

    (Shanghai University of Traditional Chinese Medicine)

  • Ping Tian

    (Shanghai University of Traditional Chinese Medicine)

  • Qinghua Li

    (Shanghai University of Traditional Chinese Medicine)

  • Liang Yin

    (Shanghai University of Traditional Chinese Medicine
    University of Chinese Academy of Sciences, Chinese Academy of Sciences)

Abstract

Herein, we report a copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides and 1,3-enynes, which provides a series of chiral poly-substituted pyrrolidines in high regio-, diastereo-, and enantioselectivities. Both 4-aryl-1,3-enynes and 4-silyl-1,3-enynes serve as suitable dipolarophiles while 4-alkyl-1,3-enynes are inert. Moreover, the method is successfully applied in the construction of both tetrasubstituted stereogenic carbon centers and chiral spiro pyrrolidines. The DFT calculations are also conducted, which imply a concerted mechanism rather than a stepwise mechanism. Finally, various transformations started from the pyrrolidine bearing a triethylsilylethynyl group and centered on the alkyne group are achieved, which compensates for the inertness of 4-alkyl-1,3-enynes in the present reaction.

Suggested Citation

  • Bo-Ran Wang & Yan-Bo Li & Qi Zhang & Dingding Gao & Ping Tian & Qinghua Li & Liang Yin, 2023. "Copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of 1,3-enynes and azomethine ylides," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-40409-4
    DOI: 10.1038/s41467-023-40409-4
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