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Enantioselective synthesis of saddle-shaped eight-membered lactones with inherent chirality via organocatalytic high-order annulation

Author

Listed:
  • Shao-Qing Shi

    (Jiangsu Normal University)

  • Chen-Chang Cui

    (Jiangsu Normal University)

  • Lin-Lin Xu

    (Xuzhou Medical University)

  • Jin-Peng Zhang

    (Xuzhou Medical University)

  • Wen-Juan Hao

    (Jiangsu Normal University)

  • Jianyi Wang

    (Guangxi University)

  • Bo Jiang

    (Jiangsu Normal University)

Abstract

Inherently chiral medium-ring derivatives have important applications in many research fields, such as materials science, molecular recognition, and asymmetric catalysis. However, the enantioselective assembly of these molecules, especially by organocatalytic strategies, remains a formidable challenge, and few methods are available. Here, we report the enantioselective NHC-catalyzed (NHC: N-heterocyclic carbenes) formal high-order (5 + 3) annulation of 1-(2-indolyl)naphthalen-2-ols with ynals. In the presence of an NHC pre-catalyst, base, Lewis acid and oxidant, this protocol enables the catalytic formation of C–C and C-O bonds, providing practical and facile access to an array of inherently chiral saddle-shaped eight-membered lactones featuring an oxocin-2-one scaffold with structural diversity in good efficiency and excellent enantiocontrol. Moreover, the scale-up preparation and representative late-stage transformations of the eight-membered lactones further demonstrate the application potential of this synthetic technology.

Suggested Citation

  • Shao-Qing Shi & Chen-Chang Cui & Lin-Lin Xu & Jin-Peng Zhang & Wen-Juan Hao & Jianyi Wang & Bo Jiang, 2024. "Enantioselective synthesis of saddle-shaped eight-membered lactones with inherent chirality via organocatalytic high-order annulation," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-52823-3
    DOI: 10.1038/s41467-024-52823-3
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    References listed on IDEAS

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