Synthesis of Homoallyl Ethers via Allylation of Acetals in Ionic Liquids Catalyzed by Trimethylsilyl Trifluoromethanesulfonate

Abstract

The chemoselective allylation of acetals using allyltrimethylsilane in ionic liquids is catalyzed by TMS triflate (5.0-20.0 mol %). The reaction proceeds smoothly at room temperature to afford the corresponding homoallyl ether in good yield. Since the ionic liquids are easily recovered and recycled, they are a useful alternative to dichloromethane, which is the commonly used solvent for allylations. [reaction--see text]