Bismuth triflate-catalyzed one-pot method for the conversion of aldehydes to homoallyl ethers

ORGN 597

Ram S. Mohan, Peter W. Anzalone, Patrick D. Hayes, and Russell C. Smith. Laboratory for Environment Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, 201 East Beecher Street, Bloomington, IL 61701
A one-pot synthesis of homoallyl ethers from aldehydes has been developed using bismuth triflate as a catalyst. The procedure involves in situ generation of an acetal by treatment of the corresponding aldehyde with a trialkyl orthoformate followed by allylation with allyltrimethylsilane. Bismuth compounds are attractive as reagents in organic synthesis because of their remarkably low toxicity, low cost and ease of handling. The results of this study will be presented.