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Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes

Author

Listed:
  • Shengnan Jin

    (Huaqiao University)

  • Jinxia Li

    (Southern University of Science and Technology)

  • Kang Liu

    (Huaqiao University)

  • Wei-Yi Ding

    (Southern University of Science and Technology)

  • Shuai Wang

    (Huaqiao University)

  • Xiujuan Huang

    (Huaqiao University)

  • Xue Li

    (Huaqiao University)

  • Peiyuan Yu

    (Southern University of Science and Technology)

  • Qiuling Song

    (Huaqiao University
    Henan Normal University
    Nankai University)

Abstract

Chiral organoborons are of great value in asymmetric synthesis, functional materials, and medicinal chemistry. The development of chiral bis(boryl) alkanes, especially optically enriched 1,1-diboron compounds, has been greatly inhibited by the lack of direct synthetic protocols. Therefore, it is very challenging to develop a simple and effective strategy to obtain chiral 1,1-diborylalkanes. Herein, we develop an enantioselective copper-catalyzed cascade double hydroboration of terminal alkynes and highly enantioenriched gem-diborylalkanes were readily obtained. Our strategy uses simple terminal alkynes and two different boranes to construct valuable chiral gem-bis(boryl) alkanes with one catalytic and one ligand pattern, which represents the simplest and most straightforward strategy for constructing such chiral gem-diborons.

Suggested Citation

  • Shengnan Jin & Jinxia Li & Kang Liu & Wei-Yi Ding & Shuai Wang & Xiujuan Huang & Xue Li & Peiyuan Yu & Qiuling Song, 2022. "Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes," Nature Communications, Nature, vol. 13(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31234-2
    DOI: 10.1038/s41467-022-31234-2
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    References listed on IDEAS

    as
    1. Wei Jie Teo & Xiaoxu Yang & Yeng Yeng Poon & Shaozhong Ge, 2020. "Cobalt-catalyzed deoxygenative triborylation of allylic ethers to access 1,1,3-triborylalkanes," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    2. Ming Hu & Shaozhong Ge, 2020. "Versatile cobalt-catalyzed regioselective chain-walking double hydroboration of 1,n-dienes to access gem-bis(boryl)alkanes," Nature Communications, Nature, vol. 11(1), pages 1-10, December.
    3. Shao-Hua Xiang & Bin Tan, 2020. "Advances in asymmetric organocatalysis over the last 10 years," Nature Communications, Nature, vol. 11(1), pages 1-5, December.
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    Cited by:

    1. Shanglin Chen & Ya-Nan Wang & Jinhui Xie & Wangyang Li & Mingxing Ye & Xingxing Ma & Kai Yang & Shijun Li & Yu Lan & Qiuling Song, 2024. "Chemo-, regio- and stereoselective access to polysubstituted 1,3-dienes via Nickel-catalyzed four-component reactions," Nature Communications, Nature, vol. 15(1), pages 1-14, December.
    2. Lei Dai & Xueting Zhou & Jiami Guo & Xuan Dai & Qingqin Huang & Yixin Lu, 2023. "Diastereo- and atroposelective synthesis of N-arylpyrroles enabled by light-induced phosphoric acid catalysis," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    3. Yaqin Lei & Yu Kong & Zi-Qiang Rong & Wanxiang Zhao, 2024. "Asymmetric dihydroboration of allenes enabled by ligand relay catalysis," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    4. Heng Wang & Xiaofeng Jie & Qinglei Chong & Fanke Meng, 2024. "Pathway-divergent coupling of 1,3-enynes with acrylates through cascade cobalt catalysis," Nature Communications, Nature, vol. 15(1), pages 1-10, December.

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