Halogeno Aldol Reaction of Ethyl Vinyl Ketone and Aldehydes Mediated by Titanium Tetrachloride

Abstract

A three-component halogeno aldol reaction has been developed by using titanium tetrachloride as the halogen source as well as the Lewis acid mediator. The dehydration and elimination of hydrogen chloride were inhibited by conducting the reaction at 0 °C in dichloromethane or at room temperature with a shortened reaction time. Seven examples were examined, giving good to high yields (61 - 92%) and modest stereoselectivity (syn/anti: 2.2/1.0 - 8.4/1.0).

Keywords

• halides
• aldol reaction
• titanium tetrachloride