Stetter Reaction

The Stetter Reaction, catalyzed by cyanide or a thiazolium salt, involves a 1,4-addition (conjugate addition) of an aldehyde to an α, β-unsaturated compound. This 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.

The Stetter reaction is an organic chemistry reaction that forms carbon-carbon bonds through a 1,4-addition reaction using a nucleophilic catalyst. Although the Benzoin Condensation, a related 1,2-addition reaction, has been known since the 1830s, the Stetter reaction was first reported by Dr. Hermann Stetter in 1973.The reaction provides synthetically useful 1,4-dicarbonyl compounds and related derivatives from aldehydes and Michael acceptors.

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[1]El‐Hajj T, Martin J C, Descotes G. Dérivés de l'hydroxyméthyl‐5 furfural. I. Synthése de dérivés du di‐et terfuranne[J]. Journal of Heterocyclic Chemistry, 1983, 20(1): 233-235.

[2]Kikuchi K, Hibi S, Yoshimura H, et al. Syntheses and structure− activity relationships of 5, 6, 7, 8-tetrahydro-5, 5, 8, 8-tetramethyl-2-quinoxaline derivatives with retinoic acid receptor α agonistic activity[J]. Journal of medicinal chemistry, 2000, 43(3): 409-419.

[3]Enders D, Breuer K, Runsink J, et al. The first asymmetric intramolecular Stetter reaction. Preliminary communication[J]. Helvetica chimica acta, 1996, 79(7): 1899-1902.

[4]Read de Alaniz J, Rovis T. A highly enantio-and diastereoselective catalytic intramolecular Stetter reaction[J]. Journal of the American Chemical Society, 2005, 127(17): 6284-6289.

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