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Enantioselective functionalization at the C4 position of pyridinium salts through NHC catalysis

Author

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  • Hangyeol Choi

    (Korea Advanced Institute of Science and Technology (KAIST)
    Institute for Basic Science (IBS))

  • Gangadhar Rao Mathi

    (Korea Advanced Institute of Science and Technology (KAIST)
    Institute for Basic Science (IBS))

  • Seonghyeok Hong

    (Korea Advanced Institute of Science and Technology (KAIST)
    Institute for Basic Science (IBS))

  • Sungwoo Hong

    (Korea Advanced Institute of Science and Technology (KAIST)
    Institute for Basic Science (IBS))

Abstract

A catalytic method for the enantioselective and C4-selective functionalization of pyridine derivatives is yet to be developed. Herein, we report an efficient method for the asymmetric β-pyridylations of enals that involve N-heterocyclic carbene (NHC) catalysis with excellent control over enantioselectivity and pyridyl C4-selectivity. The key strategy for precise stereocontrol involves enhancing interactions between the chiral NHC-bound homoenolate and pyridinium salt in the presence of hexafluorobenzene, which effectively differentiates the two faces of the homoenolate radical. Room temperature is sufficient for this transformation, and reaction efficiency is further accelerated by photo-mediation. This methodology exhibits broad functional group tolerance and enables facile access to a diverse range of enantioenriched β-pyridyl carbonyl compounds under mild and metal-free conditions.

Suggested Citation

  • Hangyeol Choi & Gangadhar Rao Mathi & Seonghyeok Hong & Sungwoo Hong, 2022. "Enantioselective functionalization at the C4 position of pyridinium salts through NHC catalysis," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-29462-7
    DOI: 10.1038/s41467-022-29462-7
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    References listed on IDEAS

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    1. Yuki Matsuki & Nagisa Ohnishi & Yuki Kakeno & Shunsuke Takemoto & Takuya Ishii & Kazunori Nagao & Hirohisa Ohmiya, 2021. "Aryl radical-mediated N-heterocyclic carbene catalysis," Nature Communications, Nature, vol. 12(1), pages 1-8, December.
    2. Yonghoon Moon & Bohyun Park & Inwon Kim & Gyumin Kang & Sanghoon Shin & Dahye Kang & Mu-Hyun Baik & Sungwoo Hong, 2019. "Visible light induced alkene aminopyridylation using N-aminopyridinium salts as bifunctional reagents," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
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    Cited by:

    1. Xiaochen Wang & Rongxin Yang & Binbing Zhu & Yuxiu Liu & Hongjian Song & Jianyang Dong & Qingmin Wang, 2023. "Direct allylic acylation via cross-coupling involving cooperative N‑heterocyclic carbene, hydrogen atom transfer, and photoredox catalysis," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    2. Changha Kim & Yuhyun Kim & Sungwoo Hong, 2024. "1,3-Difunctionalization of [1.1.1]propellane through iron-hydride catalyzed hydropyridylation," Nature Communications, Nature, vol. 15(1), pages 1-10, December.

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