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Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes

Author

Listed:
  • Zhenbo Yuan

    (China Pharmaceutical University)

  • Yuye Zeng

    (China Pharmaceutical University)

  • Ziwen Feng

    (China Pharmaceutical University)

  • Zhe Guan

    (China Pharmaceutical University)

  • Aijun Lin

    (China Pharmaceutical University)

  • Hequan Yao

    (China Pharmaceutical University)

Abstract

Transition-metal-catalyzed tandem Heck/carbonylation reaction has emerged as a powerful tool for the synthesis of structurally diverse carbonyl molecules, as well as natural products and pharmaceuticals. However, the asymmetric version was rarely reported, and remains a challenging topic. Herein, we describe a palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes. Alcohols, phenols and amines are employed as versatile coupling reagents for the construction of multifunctional chiral bicyclo[3.2.1]octanes with one all-carbon quaternary and two tertiary carbon stereogenic centers in high diastereo- and enantioselectivities. This study represents an important progress in both the asymmetric tandem Heck/carbonylation reactions and enantioselective difunctionalization of internal alkenes.

Suggested Citation

  • Zhenbo Yuan & Yuye Zeng & Ziwen Feng & Zhe Guan & Aijun Lin & Hequan Yao, 2020. "Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-16221-9
    DOI: 10.1038/s41467-020-16221-9
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    Cited by:

    1. Lei Su & Shen Gao & Jiawang Liu, 2024. "Enantioconvergent synthesis of axially chiral amides enabled by Pd-catalyzed dynamic kinetic asymmetric aminocarbonylation," Nature Communications, Nature, vol. 15(1), pages 1-14, December.
    2. Dongquan Zhang & Miaomiao Li & Jiajia Li & Aijun Lin & Hequan Yao, 2021. "Rhodium-catalyzed intermolecular enantioselective Alder–ene type reaction of cyclopentenes with silylacetylenes," Nature Communications, Nature, vol. 12(1), pages 1-7, December.

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