Alkylation of carbonyl compounds in the TiCl4-promoted reaction of trimethylsilyl enol ethers with epoxides

Titanium tetrachloride promoted reaction of trimethylsilyl enol ethers with ethylene oxide affords homoaldol type products in moderate/good yields. Monosubstituted epoxides react regioselectively: the nucleophilic attack of the enolate occurs at the more substituted position of propene oxide whereas epichlorohydrin reacts at the less substituted end.