Dakin–West reaction

In 2016 Schreiner and coworkers reported the first asymmetric variant of this reaction employing short oligopeptides as catalysts.

[7] However, with the addition of 4-dimethylaminopyridine (DMAP) as a catalyst, the reaction can take place at room temperature.

The reaction mechanism involves the acylation and activation of the acid 1 to the mixed anhydride 3.

Subsequent ring-opening of 6 and decarboxylation give the final keto-amide product.

This reactivity is attributed in part to generation of acetylimidazolium, a powerful cationic acetylating agent, in situ.