Stetter Reaction

Stetter Reaction

Stetter Reaction

In 1973, Hermann Stetter reported the conjugate addition of aldehydes to α, β-unsaturated compounds, which yield 1,4-dicarbonyl compounds in the presence of cyanide anion or thiazolium salt as a catalyst. Since then 1,4 addition of aldehydes to Michael acceptors in the presence of cyanide anion or thiazolium or triazolium salt catalyst has been known as Stetter reaction.
Stetter reaction competes with the corresponding 1,2-addition, which is the Benzoin Condensation. However, the Benzoin Condensation is reversible, and since the Stetter Reaction leads to more stable products, the main product will be derived from 1,4-addition.
Stetter Reaction

Mechanism of Stetter Reaction

The possible mechanism is given below-
Mechanism of Stetter Reaction

Examples of Stetter Reaction

Example of Stetter Reaction