title: A highly regio- and stereoselective synthesis of α-fluorinated imides via fluorination of chiral enamides.
abstract: A highly π-facial selective and regioselective fluorination of chiral enamides is described. The reaction involves an enantioselective fluorination exclusively at the electron-rich enamide olefin with N-F reagents such as Selectfluor and N-fluoro-benzenesulfonimide [NFSI] accompanied by trapping of the β-fluoro-iminium cationic intermediate with water. The resulting N,O-hemiacetal could be oxidized using Dess-Martin periodinane, leading to an asymmetric sequence for syntheses of chiral α-fluoro-imides and optically enriched α-fluoro-ketones.
authors.affiliation: School of Pharmaceutical Science and Technology, Key Laboratory for Modern Drug Delivery and High-Efficiency, Collaborative Innovation Center of Chemical Science and Engineering, Tianjin University , Tianjin, 300072, P. R. China.
authors.forename: Yan-Shuang
authors.initials: YS
authors.lastname: Xu
authors.forename: Yu
authors.initials: Y
authors.lastname: Tang
authors.forename: He-Jing
authors.initials: HJ
authors.lastname: Feng
authors.forename: Ji-Tian
authors.initials: JT
authors.lastname: Liu
authors.forename: Richard P
authors.initials: RP
authors.lastname: Hsung
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000577:Amides; D006845:Hydrocarbons, Fluorinated; D006847:Hydrocarbons, Iodinated; C513869:1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one