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SPA-PNN ligand for the kinetic resolution of carbocyclic and heterocyclic spiranes by asymmetric hydrogenation

Author

Listed:
  • Yong-Yao Li

    (Lanzhou University)

  • Ka Lu

    (Lanzhou University)

  • Ju-Song Yang

    (Lanzhou University)

  • Xiao-Ming Zhang

    (Lanzhou University)

  • Fu-Min Zhang

    (Lanzhou University)

  • Yong-Qiang Tu

    (Lanzhou University
    Shanghai Jiao Tong University)

Abstract

The chiral carbocyclic and heterocyclic spirane scaffolds are widely present in natural products and pharmaceutical molecules. Efficient, concise, and enantioenriched synthesis of these structures is a significant objective in both academic and industrial fields. Here, we design and synthesize a series of chiral SPA-PNN ligands, which are used to kinetically resolve racemic spirocyclic 1,3-diketones and their analogs via Ir-catalyzed asymmetric direct hydrogenation to afford the corresponding chiral spirocyclic 1,3-diketones and chiral hydroxyspiroketones. This asymmetric transformation features broad substrate scope (four different types of spirocycle), low catalyst loading (S/C = 5000), and an excellent kinetic resolution efficiency (selectivity factor of up to 207). Notably, the resulting chiral products are successfully used in the total and formal synthesis of four natural products, and in the preparation of key synthetic intermediates for structurally attractive ligands. Furthermore, control experiments and DFT calculations enable the origin of the observed enantioselectivity to be elucidated.

Suggested Citation

  • Yong-Yao Li & Ka Lu & Ju-Song Yang & Xiao-Ming Zhang & Fu-Min Zhang & Yong-Qiang Tu, 2025. "SPA-PNN ligand for the kinetic resolution of carbocyclic and heterocyclic spiranes by asymmetric hydrogenation," Nature Communications, Nature, vol. 16(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-61360-6
    DOI: 10.1038/s41467-025-61360-6
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    References listed on IDEAS

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    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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