In the presence of TiCl4, trimethylsilyl enol ethers of ketones react smoothly with ketones or aldehydes at room temperature to give the aldol type addition products, β-hydroxyketones, in good yields.
It was found that silyl enol ethers react with α,β-unsaturated ketones and esters in the presence of TiCl4 under mild (−78°C) conditions to give 1,5-dicarbonyl compounds in good yields. Further, it was also found that 1-phenyl-1,5-hexanedione and its monoacetal were obtained by the TiCl4-promoted reaction of methyl vinyl ketone ethylene acetal with α-trimethylsiloxystyrene.
Substituted pyrroles are synthesized from γ,δ-unsaturated ketone O-pentafluorobenzoyloximes by the intramolecular Heck-type amination of the olefinic moiety catalyzed by Pd(PPh3)4.
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