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Ir-catalyzed enantioselective B−H alkenylation for asymmetric synthesis of chiral-at-cage o‑carboranes

Author

Listed:
  • Ruofei Cheng

    (Chinese Academy of Sciences)

  • Jie Zhang

    (The Chinese University of Hong Kong)

  • Huifang Zhang

    (Chinese Academy of Sciences
    Henan Normal University)

  • Zaozao Qiu

    (Chinese Academy of Sciences
    Chinese Academy of Sciences)

  • Zuowei Xie

    (Chinese Academy of Sciences
    The Chinese University of Hong Kong)

Abstract

The asymmetric synthesis of chiral-at-cage o-carboranes, whose chirality is associated with the substitution patterns on the polyhedron, is of great interest as the icosahedral carboranes have wide applications in medicinal and materials chemistry. Herein we report an intermolecular Ir-catalyzed enantioselective B−H alkenylation for efficient and facile synthesis of chiral-at-cage o-carboranes with new skeletons under mild reaction conditions. Generally very good to excellent yields with up to 99% ee can be achieved in this Ir-catalyzed B−H alkenylation. The enantiocontrol model is proposed based on Density Functional Theory calculations in which the use of chiral phosphoramidite ligand is essential for such asymmetric o-carborane B−H alkenylation.

Suggested Citation

  • Ruofei Cheng & Jie Zhang & Huifang Zhang & Zaozao Qiu & Zuowei Xie, 2021. "Ir-catalyzed enantioselective B−H alkenylation for asymmetric synthesis of chiral-at-cage o‑carboranes," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-27441-y
    DOI: 10.1038/s41467-021-27441-y
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    References listed on IDEAS

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    1. Fangrui Zheng & Tsz Hin Yui & Jiji Zhang & Zuowei Xie, 2020. "Synthesis and X-ray characterization of 15- and 16-vertex closo-carboranes," Nature Communications, Nature, vol. 11(1), pages 1-5, December.
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