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- Title
Stereoselective Synthesis of Polycycles Containing an Aziridine Group: Intramolecular aza-Diels-Alder Reactions of Unactivated 2H-Azirines with Unactivated Dienes.
- Authors
Xu, Hua‐Dong; Zhou, Hao; Pan, Ying‐Peng; Ren, Xin‐Tao; Wu, Hao; Han, Mei; Han, Run‐Ze; Shen, Mei‐Hua
- 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.
- Subjects
POLYCYCLIC compounds; AZIRIDINATION; STEREOSELECTIVE reactions; INTERMEDIATES (Chemistry); DIELS-Alder reaction; INTRAMOLECULAR catalysis; DIOLEFINS synthesis
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 7, p2586
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201510096