Gold(I)-Catalyzed [8+4] Cycloaddition of 1,4-All-Carbon Dipoles with Tropone
Shouzhi Zhang, Ruyu Xie, Aijie Tang, Panpan Chen, Zhiqiang Zhao, Maozhong Miao, Hongjun Ren
Abstract
Herein, we describe a gold(I)-catalyzed generation of nonclassical gold-containing 1,4-all-carbon dipoles from cycloisomerization/1,2-carbene transfer/ring opening cascade reactions of readily accessible allenyl ketones bearing a cyclopropyl moiety and its cyclization with tropone. This method features an unprecedented formal [8+4] high-order cycloaddition under mild conditions for delivering structurally complex 7,7,5-tricycles in generally moderate to high yields.
Topics & Concepts
TroponeCycloisomerizationCycloadditionChemistryMoietyCatalysisCarbeneRing (chemistry)PhotochemistryMedicinal chemistryCombinatorial chemistryStereochemistryOrganic chemistryCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsSynthetic Organic Chemistry Methods