Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles
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Updated: Feb 5, 2026

In Situ Lithiated Reference Electrode: Four Electrode Design for In-operando Impedance Spectroscopy
Published on: September 12, 2018
Josep Mas-Roselló1, Mary Okoh, Jonathan Clayden
1School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK. j.clayden@bristol.ac.uk.
Abstract:
Lithiation of N'-arylureas derived from amino nitriles incorporating a (1R,2R)-2-aminocyclohexanol chiral auxiliary leads to diastereoselective migration of the aryl ring to the position α to the nitrile. The resulting N'-lithiated ureas undergo spontaneous cyclisation to iminohydantoins, which may be hydrolysed to give chiral 5,5-diarylhydantoins related to phenytoin, in enantioenriched form.
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