title: Gold-Catalyzed Vinyl Ether Hydroalkynylation: An Alternative Pathway for the Gold-Catalyzed Intermolecular Reaction of Alkenes and Alkynes.
abstract: In this report, the gold-catalyzed intermolecular reaction of vinyl ethers and terminal alkynes is investigated. Utilizing a triazole gold catalyst lessens gold decomposition in the presence of the vinyl ether and affords an alkynylation product instead of the [2 + 2] product. This protocol has been expanded to include glycal substrates, which undergo a one-pot alkynylation-Ferrier reaction to produce functionalized sugars in moderate to excellent yields with high diastereoselectivity.
authors.affiliation: The Department of Chemistry, University of South Florida , 4202 East Fowler Avenue, Tampa, Florida 33620, United States.
authors.forename: Seyedmorteza
authors.initials: S
authors.lastname: Hosseyni
authors.affiliation: The Department of Chemistry, University of South Florida , 4202 East Fowler Avenue, Tampa, Florida 33620, United States.
authors.forename: Courtney A
authors.initials: CA
authors.lastname: Smith
authors.affiliation: The Department of Chemistry, University of South Florida , 4202 East Fowler Avenue, Tampa, Florida 33620, United States.
authors.forename: Xiaodong
authors.identifier: 0000-0002-3189-1315
authors.initials: X
authors.lastname: Shi
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D050607:Organogold Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000480:Alkynes; D050607:Organogold Compounds; D014753:Vinyl Compounds; C100195:vinyl ether; D006046:Gold