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

Herbert M. Zerth, Nicholas M. Leonard and Ram S. Mohan*

*Laboratory for Environmentally Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, Illinois 61701, Email: rmohaniwu.edu

H. M. Zerth, N. M. Leonard, R. S. Mohan, Org. Lett., 2003, 5, 55-57.

DOI: 10.1021/ol0271739 (free Supporting Information)


Abstract

The chemoselective allylation of acetals catalyzed by TMS triflate proceeds smoothly at room temperature in ionic liquids to provide the corresponding homoallyl ethers in good yield. The ionic liquids can be recycled and are therefore an alternative to dichloromethane, which is the standard solvent for allylations.

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Key Words

Hosomi-Sakurai Reaction, allylation, Ionic Liquids


ID: J54-Y2003-050