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Enantioselective alkoxylation with electrogenerated chiral carbocation intermediates
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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 simple alcohols to deliver chiral tertiary ethers with high stereoselectivity. The key SN1 step proceeds via a tertiary amine-mediated proton shuttle that facilitates facial selection in reacting with carbocation. This study presents a viable electrochemical strategy for externally tuning enamine catalysis.
American Chemical Society (ACS)
Title: Enantioselective alkoxylation with electrogenerated chiral carbocation intermediates
Description:
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 simple alcohols to deliver chiral tertiary ethers with high stereoselectivity.
The key SN1 step proceeds via a tertiary amine-mediated proton shuttle that facilitates facial selection in reacting with carbocation.
This study presents a viable electrochemical strategy for externally tuning enamine catalysis.
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