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

Hartmut Schedel; Wojciech Dmowski; Klaus Burger

doi:10.1055/s-2000-8198

Synthesis 2000; 2000(12): 1681-1688
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

Hartmut Schedel^* , Wojciech Dmowski, Klaus Burger

^*Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany; Fax +49 (3 41) 9 73 65 99; E-mail: burger@organik.chemie.uni-leipzig.de

Abstract

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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

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