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Dual Brønsted Acid/Nucleophilic Activation of Carbonylimidazole Derivatives

Stephen T. Heller, Tingting Fu and Richmond Sarpong*

*Department of Chemistry, University of California, Berkeley, California 94720, United States, Email: rsarpongberkeley.edu

S. T. Heller, T. Fu, R. Sarpong, Org. Lett., 2012, 14, 1970-1973.

DOI: 10.1021/ol300339q (free Supporting Information)


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Abstract

Carbonylimidazole derivatives are highly active acylation reagents for esterification and amidation in the presence of pyridinium salts as catalysts. These reactions are thought to involve both Brønsted acid and nucleophilic catalysis. This mode of activation has been applied to the synthesis of difficult to access oxazolidinones, as well as esters and amides.

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Key Words

Oxazolidinones, Benzoates, Esters


ID: J54-Y2012-1160