Stereospecific Electrophilic Fluorocyclization of α,β-Unsaturated Amides with Selectfluor
2020
Fei, Haiyang | Xu, Zheyuan | Wu, Hongmiao | Zhu, Lin | Jalani, Hitesh B. | Li, Guigen | Fu, Yao | Lu, Hongjian
An efficient fluorocyclization of α,β-unsaturated amides through a formal halocyclization process is developed. The reaction proceeds under transition-metal-free conditions and leads to the formation of fluorinated oxazolidine-2,4-diones with excellent regio- and diastereoselectivity. The evaluation of the reaction mechanism based on preliminary experiments and density functional theory calculations suggests that a synergetic syn-oxo-fluorination occurs and is followed by an anti-oxo substitution reaction. The reaction opens a new window in the field of stereospecific fluorofunctionalization.
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