Organic Letters · 2021 · 36 citations · 42 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistryOrganometallic ChemistryHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisOrganometallic SynthesisQuinone ChemistrySubstrate ScopeSubstrate Scope EvaluationSubstrate Scope Expansion
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.
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