Passerini Reaction

Passerini Reaction



This three-component reaction between a carboxylic acid, a carbonyl compound such as a ketone or aldehyde, and an isocyanide, offers direct access to α-hydroxy carboxamides.



Mechanism
The Passerini Reaction proceeds rapidly if the reaction is performed in aprotic solvents at room temperature. High yields are obtained with high concentrations of the starting materials in the reaction mixture.
From these findings, it is assumed that the Passerini Reaction does not follow an ionic pathway. Hydrogen bonding is believed to play a crucial role in the formation of the presumed cyclic transition state for this reaction.