title: Trapping Hemiacetals with Phosphono Substituted Palladium π-Allyl Complexes for the Synthesis of Substituted Cyclic Ethers.
abstract: Oxidation of hydroxy substituted phosphono allylic carbonates gave the aldehyde substituted phosphonates in good yield. Stereospecific palladium (0)-catalyzed cyclization in the presence of methanol or water gave acetal tetrahydrofuran and tetrahydropyran vinyl phosphonate products derived from hemiacetal trapping. The tetrahydrofuran acetals undergo Lewis acid catalyzed addition of nucleophiles to give diastereoisomeric mixtures of substituted tetrahydrofurans.
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri, 63121, USA.
authors.forename: Nongnuch
authors.initials: N
authors.lastname: Sutivisedsak
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri, 63121, USA.
authors.forename: Surendra
authors.initials: S
authors.lastname: Dawadi
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri, 63121, USA.
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Spilling
keywords: Acetal; Allyl phosphonates; Catalysis; Cyclization; Palladium π-allyl; Vinyl phosphonates