4.7 Article

Construction of Bridged Aza- and Oxa-[n.2.1] Skeletons via an Intramolecular Formal [3+2] Cycloaddition of Aziridines and Epoxides with Electron-Deficient Alkenes

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 9, Pages 6426-6431

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00287

Keywords

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Funding

  1. Natural Science Foundation of Tianjin [18JCQNJC06700, 20JCYBJC00330]
  2. Training Program of Outstanding Youth Innovation Team of Tianjin Normal University
  3. Program for Innovative Research Team in University of Tianjin [TD13-5074]

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In this study, a method for intramolecular formal [3+2] cycloaddition of activated aziridines and epoxides with electron-deficient alkene was developed, enabling efficient construction of bridged aza- and oxa-[n.2.1] skeletons. This strategy proved to be highly efficient with the assistance of lithium iodide.
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

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