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Nucleophilic Catalysis by 4-(Dialkylamino)pyridines Revisited—The Search for Optimal Reactivity and Selectivity
Article first published online: 17 SEP 2004
DOI: 10.1002/anie.200460373
Copyright © 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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How to Cite
Spivey, A. C. and Arseniyadis, S. (2004), Nucleophilic Catalysis by 4-(Dialkylamino)pyridines Revisited—The Search for Optimal Reactivity and Selectivity. Angewandte Chemie International Edition, 43: 5436–5441. doi: 10.1002/anie.200460373
Publication History
- Issue published online: 13 OCT 2004
- Article first published online: 17 SEP 2004
- Abstract
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Keywords:
- asymmetric catalysis;
- esterification;
- N ligands;
- nucleophilic catalysis;
- organocatalysis
Graphical Abstract
A complex interplay between catalyst structure, acylating agent, auxiliary base, and solvent governs the reactivity and selectivity in 4-(dialkylamino)pyridine-catalyzed esterification reactions (see scheme). This highlight attempts a rationalization of the complicated mechanism and puts forward some explanations for seemingly contradictory experimental observations.