Construction of Bridged Aza- and Oxa-[<i>n</i>.2.1] Skeletons via an Intramolecular Formal [3+2] Cycloaddition of Aziridines and Epoxides with Electron-Deficient Alkenes
Siyang Xing, Yuhan Wang, Changkun Jin, Shaochen Shi, Yihui Zhang, Ziya Liao, Kui Wang, Bolin Zhu
Abstract
An intramolecular formal [3+2] cycloaddition of activated aziridines and epoxides with electron-deficient alkene has been developed for the general and efficient construction of bridged aza- and oxa-[n.2.1] (n = 3 or 4) skeletons. This strategy can be efficiently promoted by lithium iodide. To demonstrate its potential, the intramolecular formal [3+2] cycloaddition was used to access the important intermediate of homoepiboxidine.
Topics & Concepts
Intramolecular forceCycloadditionChemistryLithium iodideAlkeneIodideIntramolecular reactionLithium (medication)Formal synthesisStereochemistryMedicinal chemistryOrganic chemistryCatalysisEndocrinologyElectrolytePhysical chemistryMedicineElectrodeSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions