Annelated Pyridine Bases for the Selective Acylation of 1,2-Diols

Mayr, Stefanie and Zipse, Hendrik (2022): Annelated Pyridine Bases for the Selective Acylation of 1,2-Diols. In: European Journal of Organic Chemistry, Vol. 2022, No. 29

Abstract

A set of 24 annelated derivatives of 4-diaminopyridine (DMAP) has been synthesized and tested with respect to its catalytic potential in the regioselective acylation of 1,2-diol substrates. The Lewis basicities of the catalysts as quantified through quantum chemical calculations vary due to inductive substituent effects and intramolecular stacking interactions between side chain pi-systems and the pyridinium core ring system. The primary over secondary hydroxyl group selectivities in catalytic acylations of 1,2-diol substrates depend on the size and the steric demand of the Lewis base and the anhydride reagent.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1434-193X
• Language: English
• DFG: Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 491502892