Sc(OTf)<sub>3</sub>-Catalyzed Formal [3 + 3] Cycloaddition Reaction of Diaziridines and Quinones for the Synthesis of Benzo[<i>e</i>][1,3,4]oxadiazines
Jose Cortes Vazquez, Jacqkis Davis, В. Н. Нестеров, Hong Wang, Weiwei Luo
Abstract
A formal [3 + 3] cyclization reaction of diaziridines and quinones has been developed offering 1,3,4-oxadiazinanes in generally high yields (up to 96%). The reaction was catalyzed by Sc(OTf)3 with a large substrate scope for both diaziridines and quinones. The synergistic activation of 1,3-dipolar diaziridines and the dipolar quinones was found to be essential to enable this reaction.
Topics & Concepts
ChemistryScope (computer science)CatalysisCycloadditionComputational chemistryCombinatorial chemistryOrganic chemistryComputer scienceProgramming languageSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsAxial and Atropisomeric Chirality Synthesis