Enantioselective SN1-type Reaction via Electrochemically Generated Chiral α-Imino Carbocation Intermediate

03 May 2024, Version 2
This content is a preprint and has not undergone peer review at the time of posting.


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, thiols and water with high stereoselectivity. The key SN1 step proceeds via a tertiary amine-mediated proton shuttle that facilitates facial selection in reacting with carbocation.


chiral carbocation
electrochemical synthesis
asymmetric catalysis
amine catalysis


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