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Highly atroposelective synthesis of nonbiaryl naphthalene-1,2-diamine N-C atropisomers through direct enantioselective C-H amination

Author

Listed:
  • He-Yuan Bai

    (Shanghai Jiao Tong University)

  • Fu-Xin Tan

    (Shanghai Jiao Tong University)

  • Tuan-Qing Liu

    (Shanghai Jiao Tong University)

  • Guo-Dong Zhu

    (Shanghai Jiao Tong University)

  • Jin-Miao Tian

    (Shanghai Jiao Tong University)

  • Tong-Mei Ding

    (Shanghai Jiao Tong University)

  • Zhi-Min Chen

    (Shanghai Jiao Tong University)

  • Shu-Yu Zhang

    (Shanghai Jiao Tong University)

Abstract

Nonbiaryl N-C atropisomer is an important structural scaffold, which is present in natural products, medicines and chiral ligands. However the direct enantioselective C-H amination to access optically pure N-C atropisomer is still difficult and rare. Here we report a π-π interaction and dual H-bond concerted control strategy to develop the chiral phosphoric acids (CPAs) catalyzed direct intermolecular enantioselective C-H amination of N-aryl-2-naphthylamines with azodicarboxylates as amino sources for the construction of atroposelective naphthalene-1,2-diamines. This type of N-C atropisomers is stabilized by intramolecular hydrogen bond and the method features a broad range of substrates, high yields and ee values, providing a strategy to chirality transfer via the modification of N-C atropisomers.

Suggested Citation

  • He-Yuan Bai & Fu-Xin Tan & Tuan-Qing Liu & Guo-Dong Zhu & Jin-Miao Tian & Tong-Mei Ding & Zhi-Min Chen & Shu-Yu Zhang, 2019. "Highly atroposelective synthesis of nonbiaryl naphthalene-1,2-diamine N-C atropisomers through direct enantioselective C-H amination," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-10858-x
    DOI: 10.1038/s41467-019-10858-x
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    Cited by:

    1. Le Wang & Cheng-Long Wang & Zi-Hao Li & Peng-Fei Lian & Jun-Chen Kang & Jia Zhou & Yu Hao & Ru-Xin Liu & He-Yuan Bai & Shu-Yu Zhang, 2024. "Cooperative Cu/azodiformate system-catalyzed allylic C–H amination of unactivated internal alkenes directed by aminoquinoline," Nature Communications, Nature, vol. 15(1), pages 1-10, December.

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