title: Synthesis of fused-β-lactams through selective gold-catalyzed oxycyclization of dioxolane-tethered enynes.
abstract: The gold-catalyzed preparation of 2-azetidinone-fused oxacycles was accomplished from β-lactam-linked enynes through heterocyclization reaction taking advantage of the acetonide pendant group. While the synthesis of fused tetrahydrofuran-β-lactams from 1,3-enynes could be considered as an unusual metal-catalyzed cyclization of enynols, α-alkoxy dioxolane-tethered 1,3-enynes exclusively undergo bis-oxycyclization to afford tricyclic bridged acetals.
authors.affiliation: Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid , 28040 Madrid, Spain.
authors.forename: Benito
authors.initials: B
authors.lastname: Alcaide
authors.forename: Pedro
authors.initials: P
authors.lastname: Almendros
authors.forename: Teresa
authors.initials: T
authors.lastname: Martínez del Campo
authors.forename: M Rosario
authors.initials: MR
authors.lastname: Torres
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004148:Dioxolanes / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D008968:Molecular Conformation; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D004148:Dioxolanes; D047090:beta-Lactams; D006046:Gold; C010962:formal glycol