Gold(I)-Catalyzed Asymmetric Heterocyclization/(5 + 3) Cycloaddition of Yne-enones with Imidazolidines: Access to Cycloocta[<i>c</i>]furan Frameworks
Yuncheng Liu, Xiaoai Liu, Song Gao, Junyang Liu, Ming Lang, Shiyong Peng
Abstract
Herein, we report a gold(I)-catalyzed heterocyclization/(5 + 3) cycloaddition cascade of yne-enones with imidazolidines, providing a modular, atom-economical and efficient strategy for the synthesis of cycloocta[ c ]furans in moderate to excellent yields. This method features readily available substrates, simple operation, mild reaction conditions, and broad substrate scope. More importantly, the asymmetric version is also achieved by employing ( R )- C 2 -TunePhos ligand ( L7 ), leading to optically active cycloocta[ c ]furans with up to 98:2 er.
Topics & Concepts
ChemistryFuranCycloadditionCatalysisMedicinal chemistryCombinatorial chemistryStereochemistryOrganic chemistryCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods