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Tunable 2H-azirines for kinetically favored reactions with geminal dicarboxylic acids
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DOI：10.1016/j.tetlet.2026.156009.png)
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Abstract
En 中文
The 2H-azirine functional group reacts with carboxylic acids to generate alpha-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.
Keywords:
Azirine
Geminal dicarboxylic acid
Kinetic study
Hammett plot
Anchimeric assistance
Natural bonding orbital analysis
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1.5
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