Rearrangement of allyl homoallyl ethers to gamma,delta-unsaturated carbonyl compounds catalyzed by iridium complexes
Iridium complexes were found to promote the conversion of allyl homoallyl ethers to gamma,delta-unsaturated carbonyl compounds. For example, treatment of 1-allyl-1-allyloxycyclohexane in the presence of catalytic amounts of [Ir(cod)Cl](2), PCy(3), and Cs(2)CO(3) in toluene at 100 degrees C afforded 4-cyclohexyliden-2, 3-dimethylbutanal in 74% yield. The reaction presumably proceeds through double bond migration to allyl vinyl ethers, which then undergo the Claisen rearrangement.
Higashino
T
Department of Applied Chemistry, Faculty of Engineering & High Technology Research Center, Kansai University, Suita, Osaka 564-8680, Japan.
Sakaguchi
S
Ishii
Y