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Stereoselective Synthesis of Cyclohepta[ b ]indoles by Visible‐Light‐Induced [2+2]‐Cycloaddition/retro‐Mannich‐type Reactions
Author(s) -
Mu XinPeng,
Li YuanHe,
Zheng Nan,
Long JianYu,
Chen SiJia,
Liu BingYan,
Zhao ChunBo,
Yang Zhen
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202101104
Subject(s) - cycloaddition , chemistry , cyclobutane , moiety , stereoselectivity , photochemistry , visible spectrum , fragmentation (computing) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , ring (chemistry) , physics , optoelectronics , computer science , operating system
A novel method for the concise synthesis of cyclohepta[b]indoles in high yields was developed. The method involves a visible‐light‐induced, photocatalyzed [2+2]‐cycloaddition/ retro‐Mannich‐type reaction of enaminones. Experimental and computational studies suggested that the reaction is a photoredox process initiated by single‐electron oxidation of an enaminone moiety, which undergoes subsequent cyclobutane formation and rapidly fragmentation in a radical‐cation state to form cyclohepta[b]indoles.