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Polyfluoroarylation of oxazolones: access to non-natural fluorinated amino acids

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Abstract

Herein, conditions are provided for the formation and use of the oxazolone enolate for the nucleophilic substitution of highly fluorinated (hetero)arenes, which after unmasking yield highly fluorinated non-natural amino acids and derivatives. In addition, the properties and chemical behavior of this new class of amino acids are explored. The utility is demonstrated in the one pot synthesis of medicinally relevant 2-aminohydantoins.

Graphical abstract: Polyfluoroarylation of oxazolones: access to non-natural fluorinated amino acids

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Publication details

The article was received on 03 Mar 2017, accepted on 17 Mar 2017 and first published on 30 Mar 2017


Article type: Communication
DOI: 10.1039/C7CC01606A
Citation: Chem. Commun., 2017, Advance Article
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    Polyfluoroarylation of oxazolones: access to non-natural fluorinated amino acids

    K. A. Teegardin and J. D. Weaver, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC01606A

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