title: Enantioselective synthesis of alpha-fluorinated beta2-amino acids.
abstract: A methodology for the enantioselective synthesis of alpha-fluorinated beta2-amino acids has been developed from readily available carboxylic acids 3. Conversion to the Evan's oxazolidinone followed by enantioselective fluorination and alkylation gave 7 in high diastereomeric excess (>95%). Subsequent removal of the oxazolidinone and amination at the Bn-protected hydroxyl center gave optically active alpha-fluorinated beta2-amino acids.
authors.affiliation: School of Applied Science, Christchurch Polytechnic Institute of Technology, Christchurch, New Zealand.
authors.forename: Michael K
authors.initials: MK
authors.lastname: Edmonds
authors.forename: Florian H M
authors.initials: FH
authors.lastname: Graichen
authors.forename: James
authors.initials: J
authors.lastname: Gardiner
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Abell
mesh_terms: D000586:Amination; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D002264:Carboxylic Acids; D006845:Hydrocarbons, Fluorinated; D023303:Oxazolidinones