The 2H-azirine functional group reacts with carboxylic acids to generate α-amido ketones. Remarkably, the presence of a second carboxylic acid functionality—geminal to the first acid—increases the reaction rate 40-fold in comparison to that with a single acid. A Hammett analysis and computational modeling with Gaussian 16 provided insight into the reaction mechanism and demonstrated the tunable nature of the 2H-azirine for the potential to selectively target dicarboxylic acids over monocarboxylic acids.