title: Enantioselective fluorination of organic molecules. I. Synthetic studies of the agents for electrophilic, enantioselective fluorination of carbanions.
abstract: In order to develop novel methods for electrophilic and enantioselective fluorination of active methine compounds, preliminary experiments were carried out. The N-tosyl derivative 5 obtained from D-phenylglycine was fluorinated with FClO3 or diluted F2 gas to give the N-fluoro-N-tosyl derivative 6. N-tosyl- or N-mesyl-(S)-alpha-phenethylamine 7 or 8 was subjected to FClO3 fluorination to produce the corresponding N-fluoro derivative, 10 or 11, respectively. Enantioselective fluorination of some methine compounds was attempted employing the above N-fluoro agents. Best result was obtained when 2-benzyl-1-tetralone/KHMDS was treated with 10 to produce the fluorinated tetralone 17 in 53% yield with enantiomeric excess (ee) of 48%.
authors.affiliation: Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Takeuchi
authors.forename: A
authors.initials: A
authors.lastname: Satoh
authors.forename: T
authors.initials: T
authors.lastname: Suzuki
authors.forename: A
authors.initials: A
authors.lastname: Kameda
authors.forename: M
authors.initials: M
authors.lastname: Dohrin
authors.forename: T
authors.initials: T
authors.lastname: Satoh
authors.forename: T
authors.initials: T
authors.lastname: Koizumi
authors.forename: K L
authors.initials: KL
authors.lastname: Kirk
mesh_terms: D000838:Anions / Q000378:metabolism*; D002244:Carbon / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D005459:Fluorides / Q000737:chemistry; D005461:Fluorine / Q000378:metabolism*; D005663:Furans; D005998:Glycine / Q000031:analogs & derivatives; D006860:Hydrogen Bonding; D007202:Indicators and Reagents / Q000138:chemical synthesis*; D008956:Models, Chemical; D010627:Phenethylamines / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism; D013464:Sulfuric Acids / Q000737:chemistry
chemical_list: D000838:Anions; D005663:Furans; D007202:Indicators and Reagents; D010627:Phenethylamines; D013464:Sulfuric Acids; D005461:Fluorine; C029261:phenethylamine; C018674:tetrahydrofuran; D002244:Carbon; C046106:fluorosulfonic acid; D005459:Fluorides; D005998:Glycine