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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.

SUBMITTER: Teegardin KA

PROVIDER: S-EPMC5549939 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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

Teegardin Kip A KA Weaver Jimmie D JD

Chemical communications (Cambridge, England) 20170401 35

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. ...[more]

PMID: 28357423

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