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Synthesis of dienes from pyrrolidines using skeletal modification

Author

Listed:
  • Haitao Qin

    (Nanjing University
    Soochow University)

  • Ting Guo

    (Nanjing University)

  • Ken Lin

    (Nanjing University)

  • Guigen Li

    (Texas Tech University)

  • Hongjian Lu

    (Nanjing University
    Anhui Normal University)

Abstract

Saturated N-heterocyclic pyrrolidines are common in natural products, medicinal compounds and agrochemicals. However, reconstruction of their skeletal structures creating new chemical space is a challenging task, and limited methods exist for this purpose. In this study, we report a skeletal modification strategy for conversion of polar cyclic pyrrolidines into nonpolar linear dienes through a N-atom removal and deconstruction process. This involves N-sulfonylazidonation followed by rearrangement of the resulting sulfamoyl azide intermediates. This can be an energetically unfavorable process, which involves the formation of active C–C π bonds, the consumption of inert C–N and C–C σ bonds and the destruction of stable five-membered rings, but we have used it here to produce versatile conjugated and nonconjugated dienes with links of varying lengths. We also studied the application of this method in late-stage skeletal modification of bioactive compounds, formal traceless C(sp2)–H functionalization and formal N-atom deletion.

Suggested Citation

  • Haitao Qin & Ting Guo & Ken Lin & Guigen Li & Hongjian Lu, 2023. "Synthesis of dienes from pyrrolidines using skeletal modification," Nature Communications, Nature, vol. 14(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-43238-7
    DOI: 10.1038/s41467-023-43238-7
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    References listed on IDEAS

    as
    1. William P. Unsworth & Alyssa-Jennifer Avestro, 2021. "Nitrogen deletion offers fresh strategy for organic synthesis," Nature, Nature, vol. 593(7858), pages 203-204, May.
    2. Sean H. Kennedy & Balu D. Dherange & Kathleen J. Berger & Mark D. Levin, 2021. "Skeletal editing through direct nitrogen deletion of secondary amines," Nature, Nature, vol. 593(7858), pages 223-227, May.
    3. Jose B. Roque & Yusuke Kuroda & Lucas T. Göttemann & Richmond Sarpong, 2018. "Deconstructive diversification of cyclic amines," Nature, Nature, vol. 564(7735), pages 244-248, December.
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