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Formal [3 + 2] Cycloadditions via Indole Activation: A Route to Pyrroloindolines and Furoindolines

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成果类型:
期刊论文
作者:
Wang, Ya-Ni;Li, Tian-Ren;Zhang, Mao-Mao;Cheng, Bei-Yi;Lu, Liang-Qiu*;...
通讯作者:
Lu, Liang-Qiu;Xiao, Wen-Jing
作者机构:
[Lu, LQ; Xiao, WJ; Lu, Liang-Qiu; Li, Tian-Ren; Wang, Ya-Ni; Cheng, Bei-Yi; Xiao, Wen-Jing; Zhang, Mao-Mao] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
[Xiao, Wen-Jing] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Xiangtan 411201, Hunan, Peoples R China.
通讯机构:
[Lu, LQ; Xiao, WJ] C
[Xiao, Wen-Jing] H
Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Xiangtan 411201, Hunan, Peoples R China.
语种:
英文
期刊:
JOURNAL OF ORGANIC CHEMISTRY
ISSN:
0022-3263
年:
2016
卷:
81
期:
21
页码:
10491-10498
基金类别:
National Natural Science Foundation of ChinaNational Natural Science Foundation of China (NSFC) [21232003, 21472057, 21572074]; [201422]; [CCNU15A02007]; [2015CFA033]
机构署名:
本校为第一且通讯机构
院系归属:
化学学院
摘要:
Here, we describe a novel [3 + 2] cycloaddition of 3-substituted indoles with vinyl aziridines and vinyl epoxides that provides a straightforward approach to pyrroloindolines and furoindolines bearing vinyl groups (up to 96% yield and 9:1 dr). In contrary to previous reports involving Lewis acid activation, this work reports successful reactions based on the activation of indole using t-BuOK and BEt3 (triethylborane), thereby preserving the free N–H group on indoles. In addition, a gram-scale reaction and a ring-closing metatheis reaction are performed to p...

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