Exceptionally Mild, High‐Yield Synthesis of α‐Fluoro Acrylates.

Abstract

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Gold-Catalyzed Hydrofluorination of Electron-Deficient Alkynes: Stereoselective Synthesis of β-Fluoro Michael Acceptors

“…Monofluoroalkenes are isosteric with peptide bonds, and several bioactive compounds containing this motif have been reported. 2 Although several synthetic protocols exist to access α-fluoro, α,β-unsaturated carbonyl compoundsthe Horner−Wadsworth−Emmons reaction, 3 the Julia Olefination, 4 the Peterson Olefination, 5 and the Reformatsky reaction 6 the stereoselective synthesis of βfluoro, α,β-unsaturated carbonyl compounds has proven to be a challenge, especially if β-alkyl substituents are desired. 7 Previous methods to access (Z)-β-fluoro-α,β-unsaturated carbonyl compounds are limited by the formation of products with low diastereoselectivities or yields, 8 the requirement for prefunctionalized starting materials, 9 and narrow functional group tolerance.…”