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Synthesis 2000; 2000(12): 1681-1688
DOI: 10.1055/s-2000-8198
DOI: 10.1055/s-2000-8198
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New Stereoconservative Syntheses of β,β,β- and γ,γ,γ-Trifluoro-α-amino, α-Hydroxy, and α-Mercapto Acids and Their Incorporation into a Peptide and Depsipeptide Fragment
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Publication History
Publication Date:
31 December 2000 (online)

Syntheses of β,β,β- and γ,γ,γ-trifluoro-α-amino, α-hydroxy and α-mercapto acids using hexafluoroacetone as protecting and activating reagent are described. The key step of the syntheses is the transformation of an ω-carboxy group into a trifluoromethyl group on treatment with sulfur tetrafluoride. The carboxy activated species obtained are suitable for direct incorporation into peptide and depsipeptide fragments. RP-HPLC experiments and Mosher's TMPA method (1H and 19F) demonstrate that the reaction sequence occurs without racemization.
amino acids - heterocycles - hexafluoroacetone - lactones - peptides - sulfur tetrafluoride