title: Synthesis of α,ω-polyfluorinated α-amino acid derivatives and δ,δ-difluoronorvaline.
abstract: Intending to synthesize ω,ω-difluoroalkyl amino acid derivatives by oxidative desulfurization-fluorination reactions of suitable arylthio-2-phthalimido butanoates and pentanoates, in addition to small amounts of the target products, mainly α,ω-polyfluorinated amino acid derivatives were formed by additional sulfur-assisted α-fluorination. This novel structural motif was verified spectroscopically as well as by X-ray analysis. A plausible mechanism of formation is suggested. Using a different approach, δ,δ-difluoronorvaline hydrochloride was synthesized with at least 36% enantiomeric excess via deoxofluorination of the corresponding aldehyde.
authors: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraße 40, D-48149 Münster, Germany. haufe@uni-muenster.de and Cells-in-Motion Cluster of Excellence, Westfälische Wilhelms-Universität, Waldeyerstraße 15, D-48149 Münster, Germany.
authors: Dirk
authors: D
authors: Ulbrich
authors: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraße 40, D-48149 Münster, Germany. haufe@uni-muenster.de.
authors: Constantin G
authors: CG
authors: Daniliuc
authors: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraße 40, D-48149 Münster, Germany. haufe@uni-muenster.de and Cells-in-Motion Cluster of Excellence, Westfälische Wilhelms-Universität, Waldeyerstraße 15, D-48149 Münster, Germany.
authors: Günter
authors: G
authors: Haufe
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005461:Fluorine / Q000737:chemistry*; D054879:Halogenation; D008958:Models, Molecular; D015394:Molecular Structure; D014633:Valine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000596:Amino Acids; D005461:Fluorine; C005313:norvaline; D014633:Valine