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

Josep Mas-Roselló, Mary Okoh, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

5 Citations (Scopus)
106 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)10985-10988
Number of pages4
JournalChemical Communications
Volume54
Issue number78
Early online date10 Sep 2018
DOIs
Publication statusPublished - 7 Oct 2018

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