Anionic Bisoxazoline Ligands Enable Copper‐Catalyzed Asymmetric Radical Azidation of Acrylamides
Lianqian Wu, Zhihan Zhang, Dunqi Wu, Fei Wang, Pinhong Chen, Zhenyang Lin, Guosheng Liu
Abstract
Abstract Asymmetric radical azidation for the synthesis of chiral alkylazides remains a tremendous challenge in organic synthesis. We report here an unprecedented highly enantioselective radical azidation of acrylamides catalyzed by 1 mol % of a copper catalyst. The substrates were converted to the corresponding alkylazides in high yield with good‐to‐excellent enantioselectivity. Notably, employing an anionic cyano‐bisoxazoline (CN‐Box) ligand is crucial to generate a monomeric Cu II azide species, rather than a dimeric Cu II azide intermediate, for this highly enantioselective radical azidation.
Topics & Concepts
Enantioselective synthesisAzideCatalysisChemistryMonomerCopperYield (engineering)Ligand (biochemistry)Combinatorial chemistryPolymer chemistryOrganic chemistryMaterials sciencePolymerReceptorBiochemistryMetallurgyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions