Intramolecular Schmidt Reaction of Acyl Chlorides with Alkyl Azides: Capture of N‑Acyliminium Ion Intermediates with Aromatic rings

Intramolecular Schmidt reaction of acyl chlorides with alkyl azides through N-acyliminium ion intermediates is designed and realized. The intramolecular capture of the intermediates with aromatic rings affords several nitrogen-containing tricyclic skeletons. The important feature of the domino proce...

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Veröffentlicht in:Organic letters 2014-06, Vol.16 (11), p.2865-2867
Hauptverfasser: Li, Xiao-Jing, Qiao, Jin-Bao, Sun, Jian, Li, Xue-Qiang, Gu, Peiming
Format: Artikel
Sprache:eng
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Zusammenfassung:Intramolecular Schmidt reaction of acyl chlorides with alkyl azides through N-acyliminium ion intermediates is designed and realized. The intramolecular capture of the intermediates with aromatic rings affords several nitrogen-containing tricyclic skeletons. The important feature of the domino process is the efficiency in bond reorganization and ring formation.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol501058a