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Catalytic enantioselective intramolecular hydroamination of alkenes using chiral aprotic cyclic urea ligand on manganese (II)

Author

Listed:
  • Bin Cui

    (Hebei University of Science and Technology)

  • Yuting Zheng

    (Hebei University of Science and Technology)

  • Hui Sun

    (Hebei University of Science and Technology)

  • Huijian Shang

    (Hebei University of Science and Technology)

  • Man Du

    (Hebei University of Science and Technology)

  • Yuxuan Shang

    (King Abdullah University of Science and Technology (KAUST))

  • Cafer T. Yavuz

    (King Abdullah University of Science and Technology (KAUST))

Abstract

Asymmetric catalysis for enantioselective intramolecular hydroamination of alkenes is a critical method in the construction of enantioenriched nitrogen-containing rings, often prevalent in biologically active compounds and natural products. Herein, we demonstrate a facile enantioselective intramolecular hydroamination of alkenes for the synthesis of chiral pyrrolidine, piperidine, and indoline moieties, using a manganese (II) chiral aprotic cyclic urea catalyst. The cyclic ligand hinders the inversion of the N atom of the urea and effectively discriminate between the enantiomers of substrates. High-resolution mass spectrometry, deuterium labeling experiments, and molecular orbital energy analysis clearly reveal the intermediates and mechanism of the transformation. As a key step, oxygen coordination by chiral aprotic urea presents a robust control over the asymmetric intra-HA reaction through the involvement of a convergent assembly of two vital intermediates (Mn-N and C-Mn-Br), providing access to chiral cyclic amine systems in high yields with excellent enantioselectivity.

Suggested Citation

  • Bin Cui & Yuting Zheng & Hui Sun & Huijian Shang & Man Du & Yuxuan Shang & Cafer T. Yavuz, 2024. "Catalytic enantioselective intramolecular hydroamination of alkenes using chiral aprotic cyclic urea ligand on manganese (II)," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-50757-4
    DOI: 10.1038/s41467-024-50757-4
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    References listed on IDEAS

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    1. Xuzhong Shen & Xu Chen & Jieping Chen & Yufeng Sun & Zhaoyang Cheng & Zhan Lu, 2020. "Ligand-promoted cobalt-catalyzed radical hydroamination of alkenes," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
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