Construction of <scp>3‐Azabicyclo</scp>[3.1.0]hexane Backbone by the Reaction of Allenes with Allylamines <i>via</i> Tandem Michael Addition and <scp>Copper‐Mediated</scp> Oxidative Carbanion Cyclization
Hui Xu, Teng Han, Xiaoyan Luo, Wei‐Ping Deng
Abstract
Main observation and conclusion A facile synthetic method for the construction of 3‐azabicyclo[3.1.0]hexane in the presence of copper catalyst system was developed. The reaction proceeds through Michael addition of allylamines with allenes followed by copper‐mediated intramolecular oxidative carbanion 5‐exo‐trig radical cyclization, affording potential biologically active 3‐azabicyclo[3.1.0]hexane derivatives in moderate to high yields (42%—85%).
Topics & Concepts
ChemistryCarbanionHexaneTandemCopperMichael reactionIntramolecular forceOxidative phosphorylationMedicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryCatalysisBiochemistryComposite materialMaterials scienceCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCatalytic Alkyne Reactions