Enantioselective S<sub>N</sub>1-type reaction via electrochemically generated chiral α-Imino carbocation intermediate.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 39134515.
- Also identified by DOI 10.1038/s41467-024-50945-2 and PMC identifier 11319787.
- Licence recorded as CC BY-NC-ND.
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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 S<sub>N</sub>1 step proceeds via a tertiary amine-mediated proton shuttle that facilitates facial selection in reacting with carbocation.