Hexafluoroacetone as a protecting and activating reagent: Synthesis of new types of fluoro-substituted alpha-amino, alpha-hydroxy and alpha-mercapto acids

摘要

Starting from (S)-aspartic, (S)-malic, (S)-citramalic and (S,R)-thiomalic acid, new types of 4,4-difluoro-substituted alpha-amino-, alpha-hydroxy- and alpha-mercaptopentanoic acids have been synthesized, applying hexafluoroacetone as protecting and activating reagent. The new partially fluorinated alpha-functionalized carboxylic acids represent interesting monomers for peptide and depsipeptide modification and for rational design and elucidation of secondary structure.