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Deconstructive diversification of cyclic amines

Author

Listed:
  • Jose B. Roque

    (University of California)

  • Yusuke Kuroda

    (University of California)

  • Lucas T. Göttemann

    (University of California)

  • Richmond Sarpong

    (University of California)

Abstract

Deconstructive functionalization involves carbon–carbon (C–C) bond cleavage followed by bond construction on one or more of the constituent carbons. For example, ozonolysis1 and olefin metathesis2,3 have allowed each carbon in C=C double bonds to be viewed as a functional group. Despite the substantial advances in deconstructive functionalization involving the scission of C=C double bonds, there are very few methods that achieve C(sp3)–C(sp3) single-bond cleavage and functionalization, especially in relatively unstrained cyclic systems. Here we report a deconstructive strategy to transform saturated nitrogen heterocycles such as piperidines and pyrrolidines, which are important moieties in bioactive molecules, into halogen-containing acyclic amine derivatives through sequential C(sp3)–N and C(sp3)–C(sp3) single-bond cleavage followed by C(sp3)–halogen bond formation. The resulting acyclic haloamines are versatile intermediates that can be transformed into various structural motifs through substitution reactions. In this way we achieve the skeletal remodelling of cyclic amines, an example of scaffold hopping. We demonstrate this deconstructive strategy by the late-stage diversification of proline-containing peptides.

Suggested Citation

  • 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.
  • Handle: RePEc:nat:nature:v:564:y:2018:i:7735:d:10.1038_s41586-018-0700-3
    DOI: 10.1038/s41586-018-0700-3
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    Citations

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    Cited by:

    1. 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.
    2. Ruining Li & Ya Dong & Shah Nawaz Khan & Muhammad Kashif Zaman & Junliang Zhou & Pannan Miao & Lifu Hu & Zhankui Sun, 2022. "Decarboxylative oxidation-enabled consecutive C-C bond cleavage," Nature Communications, Nature, vol. 13(1), pages 1-12, December.
    3. Hong Lu & Yu Zhang & Xiu-Hong Wang & Ran Zhang & Peng-Fei Xu & Hao Wei, 2024. "Carbon–nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes," Nature Communications, Nature, vol. 15(1), pages 1-8, December.

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