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Synthesis 2005(16): 2661-2663  
DOI: 10.1055/s-2005-872112
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Trimethylsilyl Trifluoromethanesulfonate Catalyzed One-Pot Method for the Conversion of Aldehydes to Homoallyl Ethers in an Ionic Liquid

Peter W. Anzalone, Ram S. Mohan*
Laboratory for Environment Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, IL 61701, USA
e-Mail: rmohan@iwu.edu;
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Publication History

Received 3 April 2005
Publication Date:
04 August 2005 (online)

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Abstract

A mild method for the trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed one-pot synthesis of homoallyl ethers from aldehydes has been developed in the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate ([bmim] [OTf]). The advantages of this method include the use of a recyclable ionic liquid, facile product isolation without employing excess organic solvent, elimination of an aqueous waste stream, and mild reaction conditions.

Keywords

ionic liquids - homoallyl ethers - aldehydes - allylations