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A Highly Regio- and Stereoselective Synthesis of α-Fluorinated Imides via Fluorination of Chiral Enamides

Author:
Xu, Yan-Shuang, Tang, Yu, Feng, He-Jing, Liu, Ji-Tian, Hsung, Richard P.
Source:
Organic letters 2015 v.17 no.3 pp. 572-575
ISSN:
1523-7052
Subject:
chemical reactions, chemical structure, enantioselectivity, imides, olefin, regioselectivity, stereoselective synthesis
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.
Agid:
5790139