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Copper-catalysed asymmetric reductive cross-coupling of prochiral alkenes

Author

Listed:
  • Wan Seok Yoon

    (Sungkyunkwan University)

  • Won Jun Jang

    (Sungkyunkwan University
    Dong-A University)

  • Woojin Yoon

    (Ajou University)

  • Hoseop Yun

    (Ajou University)

  • Jaesook Yun

    (Sungkyunkwan University)

Abstract

Asymmetric construction of C(sp3)–C(sp3) bond with good stereocontrol of the two connecting carbon centres retaining all carbon or hydrogen substituents is a challenging target in transition metal catalysis. Transition metal-catalysed reductive coupling of unsaturated π-substrates is considered as a potent tool to expediently develop the molecular complexity with high atom efficiency. However, such an asymmetric and intermolecular process has yet to be developed fully. Herein, we report an efficient strategy to reductively couple two prochiral conjugate alkenes using a copper-catalysed tandem protocol in the presence of diboron. Notably, this transformation incorporates a wide range of terminal and internal enynes as coupling partners and facilitates highly diastereo- and enantioselective synthesis of organoboron derivatives with multiple adjacent stereocentres in a single operation.

Suggested Citation

  • Wan Seok Yoon & Won Jun Jang & Woojin Yoon & Hoseop Yun & Jaesook Yun, 2022. "Copper-catalysed asymmetric reductive cross-coupling of prochiral alkenes," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30286-8
    DOI: 10.1038/s41467-022-30286-8
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    References listed on IDEAS

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    1. Yuqiang Li & Yixin Luo & Long Peng & Yangyang Li & Binzhi Zhao & Wang Wang & Hailiang Pang & Yi Deng & Ruopeng Bai & Yu Lan & Guoyin Yin, 2020. "Reaction scope and mechanistic insights of nickel-catalyzed migratory Suzuki–Miyaura cross-coupling," Nature Communications, Nature, vol. 11(1), pages 1-13, December.
    2. Chang-Yun Shi & Zhi-Zhou Pan & Ping Tian & Liang Yin, 2020. "Copper(I)-catalyzed asymmetric 1,6-conjugate allylation," Nature Communications, Nature, vol. 11(1), pages 1-10, December.
    3. Fanke Meng & Xiben Li & Sebastian Torker & Ying Shi & Xiao Shen & Amir H. Hoveyda, 2016. "Catalytic enantioselective 1,6-conjugate additions of propargyl and allyl groups," Nature, Nature, vol. 537(7620), pages 387-393, September.
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