Dakin-West Reaction

H. D. Dakin, R. West, J. Biol. Chem. 78, 91, 745, 757 (1928).

Reaction of α-amino acids with acetic anhydride in the presence of base to give α-acetamido ketones. The reaction occurs via the intermediate azlactone:



Mechanism: R. Knorr, R. Huisgen, Ber. 103, 2598 (1970); W. Steglich, et al., Chem. Ber. 104, 3644 (1971); G. Holfe et al., Chem. Ber. 105, 1718 (1972); N. Allinger et al., J. Org. Chem. 39, 1730 (1974); M. Kawase et al., Chem. Pharm. Bull. 48, 114 (2000). Synthetic applications: J. R. Casimir et al., Tetrahedron Letters 36, 4797 (1995); T. T. Curran, J. Chem. 74, 107 (1995). Review: G. L. Buchanan, Chem. Soc. Rev. 17, 91 (1988).