TiCl₃(OTf) and TiO(TFA)₂ Efficient Catalysts for Ring Opening of Epoxides with Alcohols, Acetic Acid and Water

Abstract

TiCl₃(OTf) and TiO(TFA)₂ can efficiently catalyze nucleophilic ring opening of epoxides in primary, secondary and tertiary alcohols, acetic acid and water to give the corresponding β-alkoxy alcohols, β-acetoxy alcohols and vicinal diols with high stereo- and regioselectivity in excellent yields. The reaction of optically active styrene oxide in MeOH with two titanium reagents was found to be highly stereospecific and afforded the corresponding S-(+)-2-methoxy-2-phenyl ethanol in 89-95% ee.