A Photoredox-Induced Stereoselective Dearomative Radical (4+2)-Cyclization/1,4-Addition Cascade for the Synthesis of Highly Functionalized Hexahydro-1H-carbazoles
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- 作者：Dirk Alpers ; Malte Gallhof ; Julian Witt ; Dr. Frank Hoffmann and Prof. Dr. Malte Brasholz
- 刊名：Angewandte Chemie International Edition
- 出版年：2017
- 出版时间：January 24, 2017
- 年：2017
- 卷：56
- 期：5
- 页码：1402-1406
- 全文大小：1221K
- ISSN：1521-3773
文摘
A stereoselective synthesis of functionalized hexahydrocarbazoles was developed based on an unprecedented photoredox-induced dearomative radical (4+2)-cyclization/1,4-addition cascade between 3-(2-iodoethyl)indoles and acceptor-substituted alkenes. The title reaction simultaneously generates three C−C bonds and one C−H bond, along with three contiguous stereogenic centers. The hexahydro-1H-carbazole products are highly valuable intermediates for the synthesis of novel antibiotics, as well as unnatural ring homologues of polycyclic indoline alkaloids.