One-Pot Synthesis of Tetrahydrofuran Derivatives from Allylic Alcohols and Vinyl Ethers by Means of Palladium(II) Acetate

Article abstract of DOI:10.1246/bcsj.62.2050

Reaction of allylic alcohol with vinyl ether in the presence of Pd(OAc)2 afforded furan derivatives in good yield.Pd(OAc)2 was essential for the reaction.PdCl2 complex did not afford cyclized product but gave acetal exclusively.Three components were combined at once to produce 4-(3-butenyl)-2-butoxy-4-methyltetrahydrofuran upon treatment of a mixture of 2-methyl-2-propen-1-ol, butyl vinyl ether, and allyl bromide.The reaction could successfully be extended to the synthesis of nitrogen containing heterocycles by use of N-tosyl allylic amines in place of allylic alcohols.