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.
A tandem sequence of 5-endo halolactamization and direct C-H oxidative functionalization is described. A range of β-halo-pyrrolidinones can be efficiently synthesized using this method, making it an excellent approach for constructing natural products containing pyrrolidinones.
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