A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy Towards Oxazocine Scaffolds
Julian Garrec, Alexis Archambeau, Anaïs Scuiller, Xueyang Liu, Marie Cordier≈
Abstract
Abstract A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.
Topics & Concepts
CycloadditionRegioselectivityHydroxymethylCatalysisPalladiumChemistryCombinatorial chemistryStereochemistryOrganic chemistrySynthesis and Biological EvaluationCatalytic C–H Functionalization MethodsSynthesis of heterocyclic compounds