Issue 35, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
03 Mar 2017
Accepted
17 Mar 2017
First published
30 Mar 2017

Chem. Commun., 2017,53, 4771-4774

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

K. A. Teegardin and J. D. Weaver, Chem. Commun., 2017, 53, 4771 DOI: 10.1039/C7CC01606A

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