Photocatalytic (3 + 3) Annnulation of Vinyldiazo Compounds and Aminocyclopropanes
Sen Li, Lei Zhou
Abstract
A (3 + 3) annulation of aminocyclopropanes and vinyldiazo compounds enabled by organo-photocatalysis is described. The reaction allows the regioselective synthesis of cyclohexenes bearing adjacent amino and carbonyl groups with broad functional group tolerance. In a departure from previous reports, our work demonstrated that a distonic radical cation can be preferentially intercepted by weakly nucleophilic vinyldiazo compounds, followed by an exclusive 6- endo radical cyclization for ring closure. Based on the interaction between adjacent amino and ester groups, the products can be further converted to cyclohexene-fused 1,3-oxazinane and azetidine.
Topics & Concepts
ChemistryAzetidineNucleophileRegioselectivityPhotocatalysisAnnulationCyclohexeneRing (chemistry)Functional groupGroup (periodic table)Medicinal chemistryCatalysisPhotochemistryOrganic chemistryStereochemistryPolymerCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions