title: Gold-catalyzed oxidative reactions of propargylic carbonates involving 1,2-carbonate migration: stereoselective synthesis of functionalized alkenes.
abstract: A gold-catalyzed oxidative reaction of propargylic carbonates or acetates using 3,5-dichloropyridine as the oxidant has been developed. The reaction provides efficient access to α-functionalized-α,β-unsaturated ketones with excellent regio- and diastereocontrol via a regioselective attack of the N-oxide to the gold-activated alkyne followed by a 1,2-carbonate migration. In addition, the alkene products could be further transformed into the valuable 5-hydroxycyclopent-2-enones via cyclocondensation with acetone or cyclodimerization under basic conditions.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, People's Republic of China.
authors.forename: Ning
authors.initials: N
authors.lastname: Sun
authors.forename: Ming
authors.initials: M
authors.lastname: Chen
authors.forename: Yuanhong
authors.initials: Y
authors.lastname: Liu