A highly regio- and stereoselective synthesis of α-fluorinated imides via fluorination of chiral enamides.
作者： Yan-Shuang Xu , Yu Tang , He-Jing Feng , Ji-Tian Liu , Richard P. Hsung
DOI: 10.1021/OL503591D
关键词:
摘要: A highly π-facial selective and regioselective fluorination of chiral enamides is described. The reaction involves an enantioselective exclusively at the electron-rich enamide olefin with N–F reagents such as Selectfluor N-fluoro-benzenesulfonimide [NFSI] accompanied by trapping β-fluoro-iminium cationic intermediate water. resulting N,O-hemiacetal could be oxidized using Dess-Martin periodinane, leading to asymmetric sequence for syntheses α-fluoro-imides optically enriched α-fluoro-ketones.
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