Enantioselective acyl-transfer catalysis by fluoride ions

Abstract

The asymmetric nucleophilic catalysis by fluoride ions at a carbon-based electrophile has been demonstrated for the first time. Using a library of ad hoc designed bifunctional phase-transfer catalysts in which both the anion and the cation are directly involved in the reaction, the desymmetrisation of meso-succinic and -glutaric anhydrides is possible. ¹⁹F NMR spectroscopic studies support the intermediacy of an acyl fluoride intermediate.