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Iron(III) p-Toluenesulfonate Catalyzed Synthesis of Homoallyl Ethers from Acetals and Aldehydes

Ram S. Mohan, Illinois Wesleyan University
Matthew J. Spafford
Erin D. Anderson
Joshua R. Lacey
Ann C. Palma

Abstract

Iron(III) p-toluenesulfonate, Fe(OTs)3.6H20, is an inexpensive, versatile and commercially available catalyst for the allylation of acetals using allyltrimethylsilane to yield homoallyl ethers in moderate to good yields. The one-pot conversion of aldehydes to homoallyl ethers using alkoxysilanes has also been accomplished using Fe(OTs)3.6H20 as a catalyst. The use of mild reaction conditions and a relatively non-corrosive catalyst make this method an attractive option for the synthesis of a range of homoallyl ethers.

Suggested Citation

Ram S. Mohan, Matthew J. Spafford, Erin D. Anderson, Joshua R. Lacey, and Ann C. Palma. "Iron(III) p-Toluenesulfonate Catalyzed Synthesis of Homoallyl Ethers from Acetals and Aldehydes" Tetrahedron Letters 48 (2007): 8665-8667.
Available at: http://works.bepress.com/ram_mohan/3