title: Conjugate hydrotrifluoromethylation of α,β-unsaturated acyl-oxazolidinones: synthesis of chiral fluorinated amino acids.
abstract: A novel conjugate hydrofluoroalkylation of α,β-unsaturated acyl-oxazolidinones is described. Using this method, enantiomerically pure β-trifluoromethylated amino acids were prepared. Trifluorovaline and trifluoroisoleucine were incorporated into peptides and found to show extremely low α-helix propensities.
authors.affiliation: Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, D-14195 Berlin, Germany.
authors.forename: Holger
authors.initials: H
authors.lastname: Erdbrink
authors.forename: Ilona
authors.initials: I
authors.lastname: Peuser
authors.forename: Ulla I M
authors.initials: UI
authors.lastname: Gerling
authors.forename: Dieter
authors.initials: D
authors.lastname: Lentz
authors.forename: Beate
authors.initials: B
authors.lastname: Koksch
authors.forename: Constantin
authors.initials: C
authors.lastname: Czekelius
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D023303:Oxazolidinones