Stereoselective Synthesis of Cyclohepta[ b ]indoles by Visible‐Light‐Induced [2+2]‐Cycloaddition/retro‐Mannich‐type Reactions | Zendy

Mu XinPeng | Zendy; Li YuanHe | Zendy; Zheng Nan | Zendy; Long JianYu | Zendy; Chen SiJia | Zendy; Liu BingYan | Zendy; Zhao ChunBo | Zendy; Yang Zhen | Zendy

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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.

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