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.

SUBMITTER: Xu YS 

PROVIDER: S-EPMC4540344 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature