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

Chem Commun (Camb). 2018 Sep 27;54(78):10985-10988. doi: 10.1039/c8cc06833j.

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.