Abstract
Abstract Metal-free electrophilic fluoro-cyclizations of the respective unsaturated N-hydroxy- and N-acetoxy-amides under action of the 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2 2 2]octane bis(tetrafluoroborate) (F-TEDA-BF4; trade name Selectfluor™) and F-TEDA-FAP (FAP = [(C2F5)3PF3]−) were carried out in organic solvents and ionic liquid 1-ethyl-3-methylimidazolium triflate. The fluoro-cyclization of trans-N-acetoxy-4-phenylbut-3-enamide (1), trans-N-hydroxy-4-phenylbut-3-enamide (2), N-hydroxy-4-phenylpent-4-enamide (3) and N-acetoxy-4-phenylpent-4-enamide (4) results in the formation of cyclic imidates. The influence of the nature of fluorinating reagent and solvent on the stereoselectivity of fluoro-cyclization is discussed.
Published Version
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