Dakin-West reaction

Schematic of the Dakin-West reaction. Reagents: amino acid, anhydride, base (pyridine), heat. Product: acylamino ketone.

The Dakin-West reaction is an organic reaction used to convert an amino acid and an anhydride to an acylamino ketone using a base and thermal conditions. The reaction begins with acylation of the amino acid on both terminals, first on the amine group, and then on the carboxylic acid group. An intramolecular reaction then follows to give a lactone intermediate. A series of addition and elimination steps and the release of carbon dioxide gas provide the acylamino ketone product.[1][2][3]

Mechanism

Mechanism of the Dakin-West reaction.

References:

1.
Dakin, H. D.; West, R. J. Biol. Chem. 1928, 78, 91
2.
Dakin, H. D.; West, R. J. Biol. Chem. 1928, 78, 745
3.
Dakin, H. D.; West, R. J. Biol. Chem 1928, 78, 757