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Atroposelective synthesis of biaxial bridged eight-membered terphenyls via a Co/SPDO-catalyzed aerobic oxidative coupling/desymmetrization of phenols

Author

Listed:
  • Shuang-Hu Wang

    (Shanghai Jiao Tong University)

  • Shi-Qiang Wei

    (Shanghai Jiao Tong University)

  • Ye Zhang

    (Shanghai Jiao Tong University)

  • Xiao-Ming Zhang

    (Lanzhou University)

  • Shu-Yu Zhang

    (Shanghai Jiao Tong University)

  • Kun-Long Dai

    (Shanghai Jiao Tong University)

  • Yong-Qiang Tu

    (Shanghai Jiao Tong University
    Lanzhou University)

  • Ka Lu

    (Lanzhou University)

  • Tong-Mei Ding

    (Shanghai Jiao Tong University)

Abstract

Bridged chiral biaryls are axially chiral compounds with a medium-sized ring connecting the two arenes. Compared with plentiful methods for the enantioselective synthesis of biaryl compounds, synthetic approaches for this subclass of bridged atropisomers are limited. Here we show an atroposelective synthesis of 1,3-diaxial bridged eight-membered terphenyl atropisomers through an Co/SPDO (spirocyclic pyrrolidine oxazoline)-catalyzed aerobic oxidative coupling/desymmetrization reaction of prochiral phenols. This catalytic desymmetric process is enabled by combination of an earth-abundant Co(OAc)2 and a unique SPDO ligand in the presence of DABCO (1,4-diaza[2.2.2]bicyclooctane). An array of diaxial bridged terphenyls embedded in an azocane can be accessed in high yields (up to 99%) with excellent enantio- (>99% ee) and diastereoselectivities (>20:1 dr).

Suggested Citation

  • Shuang-Hu Wang & Shi-Qiang Wei & Ye Zhang & Xiao-Ming Zhang & Shu-Yu Zhang & Kun-Long Dai & Yong-Qiang Tu & Ka Lu & Tong-Mei Ding, 2024. "Atroposelective synthesis of biaxial bridged eight-membered terphenyls via a Co/SPDO-catalyzed aerobic oxidative coupling/desymmetrization of phenols," Nature Communications, Nature, vol. 15(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-48858-1
    DOI: 10.1038/s41467-024-48858-1
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    References listed on IDEAS

    as
    1. Shuai Zhu & Ye-Hui Chen & Yong-Bin Wang & Peiyuan Yu & Shao-Yu Li & Shao-Hua Xiang & Jun-Qi Wang & Jian Xiao & Bin Tan, 2019. "Organocatalytic atroposelective construction of axially chiral arylquinones," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
    2. Pei-Chao Zhang & Yin-Lin Li & Jiafeng He & Hai-Hong Wu & Zhiming Li & Junliang Zhang, 2021. "Simultaneous construction of axial and planar chirality by gold/TY-Phos-catalyzed asymmetric hydroarylation," Nature Communications, Nature, vol. 12(1), pages 1-8, December.
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