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. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.