The Dakin-West reaction uses a base to convert an amino acid and anhydride to an acylamino ketone. Acylation of both the nitrogen atom and the carboxylic acid group occur first, followed by an intramolecular acyl substitution, producing a protonated oxazolone intermediate. Further acylation of the oxazolone, acetoxy group additions, and release of carbon dioxide gas result in the final acylamino ketone product.

• Reagents: Base (Pyridine, Alkylpyridine, Sodium Acetate), Solvent (Pyridine, Et₃N)
• Reactant: α-Amino Acid, Anhydride (Acetic, Propionic, etc.)
• Product: α-Acylamino Ketone
• Type of Reaction: Nucleophilic Acyl Substitution

Mechanism

Original Paper

Related Compounds