Photocatalytic Azetidine Synthesis by Aerobic Dehydrogenative [2 + 2] Cycloadditions of Amines with Alkenes
Rajesh Dasi, Alexander Villinger, Malte Brasholz
Abstract
Photocatalytic dehydrogenative [2 + 2] cycloadditions between amines and alkenes were developed that allow for the stereoselective and high-yielding synthesis of functionalized azetidines. The oxidative formal Aza Paternò–Büchi reactions are induced by photoredox-catalyzed aerobic oxidation of dihydroquinoxalinones 1 as the amines, and in the presence of structurally diverse alkenes 3 intermolecular [2 + 2] cyclization to dihydro-1H-azeto[1,2-a]quinoxalin-3(4H)-ones 4 occurs. The utility of the method is illustrated by the selective conversion of amino acid derived dihydroquinoxalinones 1, including oxidation-prone lysine and tryptophan derivatives.
Topics & Concepts
ChemistryStereoselectivityPhotocatalysisIntermolecular forceAzetidineOxidative phosphorylationAmino acidCatalysisOrganic chemistryCombinatorial chemistryMoleculeBiochemistrySynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsSynthesis and Biological Evaluation