THE SAEGUSA OXIDATION AND RELATED PROCEDURES

摘要

α,β-Unsaturated carbonyl compounds are highly useful synthetic materials in organic synthesis, and regioselective dehydrogenation of carbonyl compounds to the corresponding α,β-un saturated carbonyl compounds is an important transformation in synthetic chemistry. One-pot, palladium-mediated dehydrogenation reactions of ketones, aldehydes, esters, lactones, and amides are known, but such reactions are limited primarily to simple substrates. Moreover, they suffer from lack of regiocontrol in the case of unsymmetrical ketones. In 1977, Ito, Hirato, and Saegusa reported the conversion of silyl enol ethers to the corresponding αβ-unsaturated ketones and aldehydes using stoichiometric or substoichiometric amounts of palladium(II) salts. Although silyl enol ethers are easily prepared from saturated ketones or aldehydes, several years passed before the first application of the Saegusa Reaction was reported.