Stork Reaction

Abstract It is an enamine, an effective enol synthon, mediated alkylation or acylation at the α‐carbon of the carbonyl compounds (i.e., aldehyde or ketone) and the enamine‐based alkylation is referred to as the Stork alkylation, and the comparable acylation is termed as the Stork acylation. All these reactions are generally referred to as the Stork reaction. The study finds that the use of enamine as the enol synthon can effectively reduce the possibility of overalkylation. In addition, the double acylation of enamine also occurs when propionyl chloride or benzoyl chloride is used. It has been found that hexamethylenimine produces a high yield of monoalkylated ketones, whereas enamine from piperidine gives a low yield of monoalkylated ketones. The reaction between carbonyl compounds and primary amines usually gives imines, whereas the corresponding reaction with secondary amines yields enaminest. This general trend is also affected by the α‐substituents. This reaction has very broad application in organic synthesis.