title: Gold-catalyzed oxidative cycloadditions to activate a quinoline framework.
abstract: Going for gold! Gold-catalyzed reactions of 3,5- and 3,6-dienynes with 8-alkylquinoline oxides results in an oxidative cycloaddition with high stereospecificity (see scheme; EWG = electron-withdrawing group); this process involves a catalytic activation of a quinoline framework. The reaction mechanism involves the intermediacy of α-carbonyl pyridinium ylides (I) in a concerted [3+2]-cycloaddition with a tethered alkene.
authors.affiliation: Department of Chemistry, National Tsing Hua University, Hsinchu, 30013 (Taiwan), Fax: (+886) 3-5711082.
authors.forename: Deepak B
authors.initials: DB
authors.lastname: Huple
authors.forename: Satish
authors.initials: S
authors.lastname: Ghorpade
authors.forename: Rai-Shung
authors.initials: RS
authors.lastname: Liu
keywords: catalysis; cycloaddition; gold; oxidative cyclization; stereoselectivity