Visible-Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cyclohepta[b]indoles: Access toC,N-Diacyliminium Ions

被引：22

作者：

Frahm, Mario ^{[1
]}

von Drathen, Thorsten ^{[2
]}

Gronbach, Lisa Marie ^{[1
]}

Voss, Alice ^{[1
]}

Lorenz, Felix ^{[1
]}

Bresien, Jonas ^{[1
]}

Villinger, Alexander ^{[1
]}

Hoffmann, Frank ^{[2
]}

Brasholz, Malte ^{[1
]}

机构：

[1] Univ Rostock, Inst Chem, Albert Einstein Str 3A, D-18059 Rostock, Germany

[2] Univ Hamburg, Dept Chem, Martin Luther King Pl 6, D-20146 Hamburg, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 30期

关键词：

cascade reactions; indoles; N-acyliminium ions; photooxidation; singlet oxygen; N-ACYLIMINIUM IONS; INTERMOLECULAR ADDITION-REACTIONS; SINGLET OXYGEN; AMINO-ACIDS; OXIDATION; ORGANOCATALYSIS; DECOMPOSITION; ALLYLSILANES; DERIVATIVES; PEROXIDES;

D O I：

10.1002/anie.202007549

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：12450 / 12454

页数：5

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