Further Information
Literature
Related Reactions
Biginelli Reaction
Ugi Reaction
Multicomponent Reactions
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.
Recent Literature
Stereochemical Control of the Passerini Reaction
P. R. Andreana, C. C. Liu, S. L. Schreiber, Org. Lett., 2004, 6, 4231-4233.
Revisiting the Passerini Reaction under Eco-Friendly Reaction Conditions
C. K. Z. Andrade, S. C. S. Takada, P. A. Z. Suarez, M. B. Alves, Synlett, 2006,
1539-1541.
A three-component addition of isocyanides to phenol derivatives and
aldehydes in methanol forms O-arylated compounds in a new
Passerini-type reaction. The key step is an irreversible Smiles rearrangement of intermediate phenoxyimidate adducts.
L. El Kaim, M. Gizolme, L. Grimaud, Org. Lett., 2006,
8, 5021-5023.
