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Palladium-Catalyzed (3 + 2) Annulation of Azaborines with Vinyl Epoxides for Constructing Polycyclic Oxazaborolidines

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    Palladium-Catalyzed (3 + 2) Annulation of Azaborines with Vinyl Epoxides for Constructing Polycyclic Oxazaborolidines
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    • Zi-Qi Zhu*
      Zi-Qi Zhu
      School of Petrochemical Engineering, Institute of Functional Heterocycles, Changzhou University, Changzhou 213164, China
      *Email: [email protected]
      More by Zi-Qi Zhu
    • Ding-Hao Ge
      Ding-Hao Ge
      School of Petrochemical Engineering, Institute of Functional Heterocycles, Changzhou University, Changzhou 213164, China
      More by Ding-Hao Ge
    • Zhi-Jie Cao
      Zhi-Jie Cao
      School of Petrochemical Engineering, Institute of Functional Heterocycles, Changzhou University, Changzhou 213164, China
      More by Zhi-Jie Cao
    • Feng Shi*
      Feng Shi
      School of Petrochemical Engineering, Institute of Functional Heterocycles, Changzhou University, Changzhou 213164, China
      School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, China
      School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China
      *Email: [email protected]; [email protected]
      More by Feng Shi
      Orcidhttps://orcid.org/0000-0003-3922-0708
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 13, 4690–4703
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    https://doi.org/10.1021/acs.joc.5c00104
    Published March 25, 2025
    Copyright © 2025 American Chemical Society
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    Abstract

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    A palladium-catalyzed (3 + 2) annulation of azaborines with vinyl epoxides has been established. By this strategy, various polycyclic oxazaborolidines with structural diversity were synthesized in generally high yields (up to 99%). The annulation can be scaled up and the polycyclic oxazaborolidines can be further functionalized through olefin metathesis and Heck reaction, which demonstrated good feasibility for downstream transformations. Moreover, the catalytic asymmetric version of this (3 + 2) annulation has been accomplished under the catalysis of palladium/chiral phosphoramidite ligand, producing chiral oxazaborolidines in overall good enantioselectivities (up to 98:2 er). This work not only represents the first catalytic asymmetric (3 + 2) annulation of 1,2-azaborines with vinyl epoxides but also offers an efficient strategy for constructing benzooxazaborolidine skeletons, particularly those in an enantioenriched fashion.

    Copyright © 2025 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.5c00104.

    • 1H and 13C{1H} NMR spectra of products (±)-3, 3, 4, and 5, and HPLC traces of products 3 (PDF)

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 13, 4690–4703
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.5c00104
    Published March 25, 2025
    Copyright © 2025 American Chemical Society
    Request reuse permissions

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