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Simultaneous construction of axial and planar chirality by gold/TY-Phos-catalyzed asymmetric hydroarylation

Author

Listed:
  • Pei-Chao Zhang

    (East China Normal University)

  • Yin-Lin Li

    (East China Normal University)

  • Jiafeng He

    (East China Normal University)

  • Hai-Hong Wu

    (East China Normal University)

  • Zhiming Li

    (Fudan University)

  • Junliang Zhang

    (Fudan University
    CAS)

Abstract

The simultaneous construction of two different chiralities via a simple operation poses considerable challenge. Herein a cationic gold-catalyzed asymmetric hydroarylation of ortho-alkynylaryl ferrocenes derivatives is developed, which enable the simultaneous construction of axial and planar chirality. The here identified TY-Phos derived gold complex is responsible for the high yield, good diastereoselectivity (>20:1 dr), high enantioselectivities (up to 99% ee) and mild conditions. The catalyst system also shows potential application in the synthesis of chiral biaryl compounds. The cause of high enantioselectivity of this hydroarylation is investigated with density functional theory caculation.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-24678-5
    DOI: 10.1038/s41467-021-24678-5
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    Cited by:

    1. 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.

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