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

Qifeng Lin, Yingdong Duan, Yao Li, Ruijun Jian, Kai Yang, Zongbin Jia, Yu Xia, Long Zhang () and Sanzhong Luo ()
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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
Sanzhong Luo: Tsinghua University

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: 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.

Date: 2024
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DOI: 10.1038/s41467-024-50945-2

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