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

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...

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Bibliographic Details
Published in:Angewandte Chemie 2016-02, Vol.128 (7), p.2586-2590
Main Authors: Xu, Hua-Dong, Zhou, Hao, Pan, Ying-Peng, Ren, Xin-Tao, Wu, Hao, Han, Mei, Han, Run-Ze, Shen, Mei-Hua
Format: Article
Language:eng ; ger
Subjects:
Alkenes
Aziridine
Chemical synthesis
Chemistry
Cycloadditionen
Diels-Alder reactions
Dienes
Heterocyclen
Kleinringsysteme
Olefins
Rings (mathematics)
Stereoselectivity
Synthesemethoden
Synthesis (chemistry)
Thermal decomposition
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Summary: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. Sichere Variante: 5‐6‐3‐ und 6‐6‐3‐Tricyclen sowie komplexere Polycyclen mit konjugiertem Aziridinring wurden durch eine intramolekulare Aza‐Diels‐Alder‐Reaktion von 2H‐Azirin hoch stereoselektiv aufgebaut. Die In‐situ‐Bildung der Azirine aus Vinylazid‐Vorstufen vermeidet Probleme durch ihre direkte Handhabung.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201510096