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Enantioselective SN1-type reaction via electrochemically generated chiral α-Imino carbocation intermediate

Author

Listed:
  • Qifeng Lin

    (Tsinghua University)

  • Yingdong Duan

    (Tsinghua University)

  • Yao Li

    (Tsinghua University)

  • Ruijun Jian

    (Tsinghua University)

  • Kai Yang

    (Tsinghua University)

  • Zongbin Jia

    (Tsinghua University)

  • Yu Xia

    (Tsinghua University)

  • Long Zhang

    (Tsinghua University
    Haihe Laboratory of Sustainable Chemical Transformations)

  • Sanzhong Luo

    (Tsinghua University
    Haihe Laboratory of Sustainable Chemical Transformations)

Abstract

Electrochemical reactions via carbocation intermediates remain fundamental transformations that build up molecular functionality and complexity in a sustainable manner. Enantioselective control of such processes is a great challenge in a highly ionic electrolyte solution. Here, we report an anodic generation of chiral α-imino carbocation intermediates by enamine catalysis. The chiral carbocation intermediates can be intercepted by a variety of nucleophiles such as alcohols, water and thiols with high stereoselectivity. The key SN1 step proceeds via a tertiary amine-mediated proton shuttle that facilitates facial selection in reacting with carbocation.

Suggested Citation

  • Qifeng Lin & Yingdong Duan & Yao Li & Ruijun Jian & Kai Yang & Zongbin Jia & Yu Xia & Long Zhang & Sanzhong Luo, 2024. "Enantioselective SN1-type reaction via electrochemically generated chiral α-Imino carbocation intermediate," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-50945-2
    DOI: 10.1038/s41467-024-50945-2
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    References listed on IDEAS

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    1. Jinbao Xiang & Ming Shang & Yu Kawamata & Helena Lundberg & Solomon H. Reisberg & Miao Chen & Pavel Mykhailiuk & Gregory Beutner & Michael R. Collins & Alyn Davies & Matthew Bel & Gary M. Gallego & Ji, 2019. "Hindered dialkyl ether synthesis with electrogenerated carbocations," Nature, Nature, vol. 573(7774), pages 398-402, September.
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