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 Environment Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, Illinois 61701
Org. Lett., 2003, 5 (1), pp 55–57
DOI: 10.1021/ol0271739
Publication Date (Web): December 10, 2002
Copyright © 2003 American Chemical Society

Abstract

Abstract Image

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.

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History

  • Published In Issue January 09, 2003
  • Received October 25, 2002

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