Visible‐Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cycloheptaindoles: Access to C,N‐Diacyliminium Ions

Visible‐Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cycloheptaindoles: Access to C,N‐Diacyliminium Ions

Tetrahydrocarbazoles and perhydrocyclohepta[b]indoles undergo a catalytic cascade singlet oxygenation in alkaline medium, which leads to chiral tricyclic perhydropyrido‐ and perhydroazepino[1,2‐a]indoles in a single operation. These photooxygenation products are new synthetic equivalents of uncommon...

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Veröffentlicht in:Angewandte Chemie 2020-07, Vol.132 (30), p.12550-12554
Hauptverfasser: Frahm, Mario, Thorsten von Drathen, Gronbach, Lisa Marie, Voss, Alice, Lorenz, Felix, Bresien, Jonas, Villinger, Alexander, Hoffmann, Frank, Brasholz, Malte
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Indoles
Ions
Oxygenation
Phosphoric acid
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Beschreibung
Zusammenfassung:Tetrahydrocarbazoles and perhydrocyclohepta[b]indoles undergo a catalytic cascade singlet oxygenation in alkaline medium, which leads to chiral tricyclic perhydropyrido‐ and perhydroazepino[1,2‐a]indoles in a single operation. These photooxygenation products are new synthetic equivalents of uncommon C,N‐diacyliminium ions and can be functionalized with the aid of phosphoric acid organocatalysis.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202007549