title: Au-catalyzed tandem cyclization/[1,2]-alkyl migration reaction of epoxy alkynes: synthesis of spiropyranones.
abstract: A novel gold-catalyzed tandem cyclization/[1,2]-alkyl migration process of epoxy alkynes to spiropyranones has been discovered. From this process, the construction of adjacent multiple stereocenters with a new quaternary carbon atom is achieved. The gold-catalyzed domino process is stereospecific with respect to the migrating carbon atom. A type of unusual C-C bond cleavage of epoxide systems has also been discovered, which can lead to the formation of two Z alkenes and a carbonyl functional group in one step with excellent stereoselectivity. Furthermore, this efficient domino process could be achieved in the presence of the simplest and least expensive gold catalyst [NaAuCl(4)].2H(2)O with a low catalyst loading.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, PR China.
authors.forename: Xing-Zhong
authors.initials: XZ
authors.lastname: Shu
authors.forename: Xue-Yuan
authors.initials: XY
authors.lastname: Liu
authors.forename: Ke-Gong
authors.initials: KG
authors.lastname: Ji
authors.forename: Hui-Quan
authors.initials: HQ
authors.lastname: Xiao
authors.forename: Yong-Min
authors.initials: YM
authors.lastname: Liang