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 å å¦ä¸ å å å·¥ç¨ å¦é ¢ 生物有机与分子工程教育部重点实验室 |