title: A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers.
abstract: The Au(I)-catalyzed cyclization of hydroxyallylic ethers to form tetrahydropyrans is reported. Employing (acetonitrile)[(o-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate, the cyclization reactions were complete within minutes to hours, depending on the substrate. The reaction progress was monitored by GC, and comparisons between substrates demonstrate that reactions of allylic alcohols are faster than the corresponding ethers. Additionally, it is reported that Reaxa QuadraPure(TM) MPA is an efficient scavenging reagent that halts the reaction progress.
authors.affiliation: Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611, U.S.A.
authors.forename: Berenger
authors.initials: B
authors.lastname: Biannic
authors.forename: Thomas
authors.initials: T
authors.lastname: Ghebreghiorgis
authors.forename: Aaron
authors.initials: A
authors.lastname: Aponick