Tetrahedron Letters p. 1049 - 1052 (1997)
Update date:2022-07-30
Topics:
Andres, Didier F.
Laurent, Eliane G.
Marquet, Bernard S.
A new synthetic method to substituted α-carboxy-γ-fluorothiophenes 2F is reported. They were prepared by the reaction between two equivalents of methyl thioglycolate anion and α-fluoro-β-(phenylthio)enones (or -enals) 1F, in DMSO (70°C) in yields ranging from 41% to 85%. We show from the reaction of (Z)-α-fluoro-β-(phenylthio)but-enone 1aF, that cyclisation to fluorothiophene 2aF occurs via the formation of stable enolates of α-fluoro-β-(dithianyl)butanone.
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