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Issue 78, 2018
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Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles

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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.

Graphical abstract: Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles

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Supplementary files

Article information


Submitted
22 Aug 2018
Accepted
07 Sep 2018
First published
10 Sep 2018

Chem. Commun., 2018,54, 10985-10988
Article type
Communication

Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles

J. Mas-Roselló, M. Okoh and J. Clayden, Chem. Commun., 2018, 54, 10985
DOI: 10.1039/C8CC06833J

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