title: ZnII - and AuI-catalyzed regioselective hydrative oxidations of 3-en-1-ynes with Selectfluor: realization of 1,4-dioxo and 1,4-oxohydroxy functionalizations.
abstract: Catalytic 1,4-dioxo functionalizations of 3-en-1-ynes to (Z)- and (E)-2-en-1,4-dicarbonyl compounds are described. This regioselective difunctionalization was achieved in one-pot operation through initial alkyne hydration followed by in situ Selectfluor oxidation. The presence of pyridine alters the reaction chemoselectivity to give 4-hydroxy-2-en-1-carbonyl products instead. A cooperative action of pyridine and Zn(II) assists the hydrolysis of key oxonium intermediate.
authors.affiliation: Department of Chemistry, National Tsing Hua University, Hsinchu, 30013 (Taiwan), Fax: (+886) 3-5711082.
authors.forename: Appaso Mahadev
authors.initials: AM
authors.lastname: Jadhav
authors.forename: Sagar Ashok
authors.initials: SA
authors.lastname: Gawade
authors.forename: Dhananjayan
authors.initials: D
authors.lastname: Vasu
authors.forename: Ramesh B
authors.initials: RB
authors.lastname: Dateer
authors.forename: Rai-Shung
authors.initials: RS
authors.lastname: Liu
keywords: 1,4-enediones; 1,4-oxohydroxy; 3-en-1-ynes; hydrative oxidations; regioselective difunctionalizations