Stereospecific Electrophilic Fluorocyclization of α,β-Unsaturated Amides with Selectfluor

Haiyang Fei, Zheyuan Xu, Hongmiao Wu, Lin Zhu, Hitesh B. Jalani, Guigen Li, Yao Fu, Hongjian Lu

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)2651-2656
Number of pages6
JournalOrganic Letters
Volume22
Issue number7
DOIs
StatePublished - Apr 3 2020

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