title: Intermolecular Homopropargyl Alcohol Addition to Alkyne and a Sequential 1,6-Enyne Cycloisomerization with Triazole-Gold Catalyst.
abstract: While gold-catalyzed homopropargyl alcohol cyclization is a known process, a triazole-gold catalyst prevented the intramolecular cyclization in the presence of terminal alkynes. As a result, an intermolecular addition to an alkyne was achieved. A sequential 1,6-enyne cycloisomerization gave the unusual 2,3-dihydrooxepine, which revealed another new reaction path. Diels-Alder reaction of oxepine followed by a 1,3-alkoxyl shift gave hydrobezofuran derivatives in high yields. Diasterioselective reaction of homopropargyl alcohol to final product enabled one-step formation of five stereogenic centers with excellent enantiomeric selectivity.
authors.affiliation: Department of Chemistry, University of South Florida , Tampa, Florida 33620, United States.
authors.forename: Seyedmorteza
authors.initials: S
authors.lastname: Hosseyni
authors.affiliation: Department of Chemistry, University of South Florida , Tampa, Florida 33620, United States.
authors.forename: Lukasz
authors.initials: L
authors.lastname: Wojtas
authors.affiliation: Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (MOE), School of Pharmacy, Shandong University , Jinan, Shandong 250012, China.
authors.forename: Minyong
authors.initials: M
authors.lastname: Li
authors.affiliation: Department of Chemistry, University of South Florida , Tampa, Florida 33620, United States.
authors.forename: Xiaodong
authors.initials: X
authors.lastname: Shi