Silver(I)-Mediated Cascade Reaction of 2-(1-Alkynyl)-2-alken-1-ones with 2-Naphthols
Zhanhuan Li, Jingyi Peng, Chonglong He, Jianfeng Xu, Hongjun Ren
Abstract
An efficient cascade reaction of 2-(1-alkynyl)-2-alken-1-ones with 2-naphthols promoted by silver trifluoroacetate is disclosed, providing an expeditious access to 1,2-dihydronaphtho[2,1-b]furans with moderate to good yields. This domino process involves highly regio- and diastereoselective sequential cyclization/nucleophilic addition/oxidative ring opening/oxa-Michael addition reactions to construct three new chemical bonds and one new five-membered ring. A gram-scale experiment and the preliminary results to develop an asymmetric variant are also presented to show the practicality and potential of the current reaction.
Topics & Concepts
ChemistryCascade reactionDominoRing (chemistry)NucleophileCascadeReaction conditionsCombinatorial chemistryMedicinal chemistryOxidative phosphorylationNucleophilic additionStereochemistryOrganic chemistryCatalysisBiochemistryChromatographyCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms