Visible-Light-Induced [4 + 3]-Annulation of Carbonyl Ylides with Alkenyl Pyrazolinone for Constructing [4.2.1]-Oxo-Bridged Oxocine Skeleton
Dongsheng Ji, Xin Zhang, Peiqin Zhang, Xiazhen Bao, Yong Yuan, Congde Huo, Peng‐Fei Xu
Abstract
Herein, we present a visible-light-induced protocol for the synthesis of highly functionalized oxo-bridged oxocine skeletons. This method generates carbenes via visible-light-induced ortho-acyl diazo compounds, which are rapidly intercepted by the oxygen atom of an intermolecular acyl group to form a cyclic 1,3-dipole. The in situ generated highly reactive 1,3-dipole undergoes a facile formal [4 + 3] cycloaddition with alkenyl pyrazolinone, yielding [4.2.1]-oxo-bridged oxocine compounds.
Topics & Concepts
AnnulationChemistryCycloadditionDiazoVisible spectrumIntermolecular forceOxygen atomPhotochemistryFunctional groupStereochemistryMoleculeMedicinal chemistryOrganic chemistryCatalysisPhysicsPolymerOptoelectronicsCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions