Stereoselective Synthesis of Polycycles Containing an Aziridine Group: Intramolecular aza-Diels–Alder Reactions of Unactivated 2H-Azirines with Unactivated Dienes

Dr. Hua-Dong Xu, Hao Zhou, Ying-Peng Pan, Xin-Tao Ren, Hao Wu, Mei Han, Run-Ze Han and Dr. Mei-Hua Shen

Article first published online: 12 JAN 2016 | DOI: 10.1002/anie.201510096

全文键连 http://onlinelibrary.wiley.com/doi/10.1002/anie.201510096/full

Abstract: Vinyl azide with a pendent diene can undergo thermal decomposition to a related azirine intermediate, which was used immediately in an intramolecular aza-Diels–Alder reaction to furnish an aziridine-containing trans-fused tricyclic core structure with excellent stereoselectivity. The method provides a facile entry to complex polycyclic alkaliods which can be further elaborated by ring-opening reactions and ring expansion of the aziridine moiety, as well as by dihydroxylation of the alkene group.