AI Article Synopsis
- The study introduces a selective method for fluorinating chiral enamides, focusing on a specific part of the molecule.
- The reaction uses N-F reagents like Selectfluor to achieve this selectivity, targeting the electron-rich part of the enamide.
- After using a specific oxidizing agent, the process allows for the creation of chiral α-fluoro-imides and optically enriched α-fluoro-ketones.
Article 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.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4540344 | PMC |
| http://dx.doi.org/10.1021/ol503591d | DOI Listing |
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