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Enantioselective acyl-transfer catalysis by fluoride ions

Author:
Craig, Ryan, Litvajova, Mili, Cronin, Sarah A., Connon, Stephen J.
Source:
Chemical communications 2018 v.54 no.72 pp. 10108-10111
ISSN:
1364-548X
Subject:
Lewis acids, Lewis bases, anhydrides, catalysts, catalytic activity, cations, chemical reactions, enantioselectivity, fluorides, nuclear magnetic resonance spectroscopy, organofluorine compounds, spectral analysis
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.
Agid:
6167928