title: Lewis acid catalyzed intramolecular condensation of ynol ether-acetals. Synthesis of alkoxycycloalkene carboxylates.
abstract: Treatment of ynol ether-tethered dialkyl acetals with catalytic quantities of scandium triflate in CH(3)CN gives rise to five-, six-, and seven-membered alkoxycycloalkene carboxylates in good to excellent yields. Tri- and tetrasubstituted carbocyclic and heterocyclic alkenes may be formed by this method, and the products obtained may serve as useful intermediates for natural product synthesis.
authors.affiliation: Department of Chemistry and Biochemistry, California State University, Northridge 18111 Nordhoff Street, Northridge, California 91330, USA.
authors.forename: Vincent
authors.initials: V
authors.lastname: Tran
authors.forename: Thomas G
authors.initials: TG
authors.lastname: Minehan
mesh_terms: D000080:Acetals / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D058116:Lewis Acids / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure; D012538:Scandium / Q000737:chemistry
chemical_list: D000080:Acetals; D002264:Carboxylic Acids; D058116:Lewis Acids; D008698:Mesylates; C436603:scandium triflate; D012538:Scandium