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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
AZIRIDINATION; STEREOSELECTIVE reactions; AZA compound synthesis; DIELS-Alder reaction; DIOLEFINS
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 7, p2540
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201510096