Title Stereoselective Synthesis of Cyclohepta[b]indoles by Visible-Light-Induced [2+2]-Cycloaddition/retro-Mannich-type Reactions
Authors Mu, Xin-Peng
Li, Yuan-He
Zheng, Nan
Long, Jian-Yu
Chen, Si-Jia
Liu, Bing-Yan
Zhao, Chun-Bo
Yang, Zhen
Affiliation Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, State Key Lab Chem Oncogen, Shenzhen 518055, Peoples R China
Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China
Peking Univ, Peking Tsinghua Ctr Life Sci, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China
Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing Natl Lab Mol Sci BNLMS, Beijing 100871, Peoples R China
Shenzhen Bay Lab, Shenzhen 518055, Peoples R China
Issue Date Apr-2021
Publisher ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Abstract 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.
URI http://hdl.handle.net/20.500.11897/610481
ISSN 1433-7851
DOI 10.1002/anie.202101104
Indexed EI
SCI(E)
Appears in Collections: 深圳研究生院待认领
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生物有机与分子工程教育部重点实验室

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