Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 30, Pages 12450-12454Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202007549
Keywords
cascade reactions; indoles; N-acyliminium ions; photooxidation; singlet oxygen
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Funding
- Deutsche Forschungsgemeinschaft (DFG) [BR 3748/2-2]
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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.
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