Issue 72, 2018

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.

Graphical abstract: Enantioselective acyl-transfer catalysis by fluoride ions

Supplementary files

Article information

Article type
Communication
Submitted
13 jul 2018
Accepted
13 aug 2018
First published
20 aug 2018

Chem. Commun., 2018,54, 10108-10111

Enantioselective acyl-transfer catalysis by fluoride ions

R. Craig, M. Litvajova, S. A. Cronin and S. J. Connon, Chem. Commun., 2018, 54, 10108 DOI: 10.1039/C8CC05692G

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