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Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction

Author

Listed:
  • Shi-Ming Xu

    (Wuhan University)

  • Liang Wei

    (Wuhan University)

  • Chong Shen

    (Wuhan University)

  • Lu Xiao

    (Wuhan University)

  • Hai-Yan Tao

    (Wuhan University)

  • Chun-Jiang Wang

    (Wuhan University
    Shanghai Institute of Organic Chemistry)

Abstract

Enantiomerically enriched indole-containing heterocycles play a vital role in bioscience, medicine, and chemistry. As one of the most attractive subtypes of indole alkaloids, highly substituted tetrahydro-γ-carbolines are the basic structural unit in many natural products and pharmaceuticals. However, the syntheses of tetrahydro-γ-carbolines with high functionalities from readily available reagents are significant challenging. In particular, the stereodivergent syntheses of tetrahydro-γ-carbolines containing multi-stereogenic centers remain quite difficult. Herein, we report an expedient and stereodivergent assembly of tetrahydro-γ-carbolines with remarkably high levels of stereoselective control in an efficient cascade process from aldimine esters and indolyl allylic carbonates via a synergistic Cu/Ir catalyst system. Control experiments-guided optimization of synergistic catalysts and mechanistic investigations reveal that a stereodivergent allylation reaction and a subsequent highly stereoselective iso-Pictet-Spengler cyclization are the key elements to success.

Suggested Citation

  • Shi-Ming Xu & Liang Wei & Chong Shen & Lu Xiao & Hai-Yan Tao & Chun-Jiang Wang, 2019. "Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction," Nature Communications, Nature, vol. 10(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-13529-z
    DOI: 10.1038/s41467-019-13529-z
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    Cited by:

    1. Cong Fu & Ling He & Hui Xu & Zongpeng Zhang & Xin Chang & Yanfeng Dang & Xiu-Qin Dong & Chun-Jiang Wang, 2024. "Modular access to chiral bridged piperidine-γ-butyrolactones via catalytic asymmetric allylation/aza-Prins cyclization/lactonization sequences," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    2. Ruimin Lu & Qinglin Zhang & Chang Guo, 2023. "Catalytic stereodivergent allylic alkylation of 2-acylimidazoles for natural product synthesis," Nature Communications, Nature, vol. 14(1), pages 1-10, December.

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