Enantioselective Radical Cyclization of Tryptamines by Visible Light-Excited Nitroxides
文献类型：期刊论文
| 作者 | Liang, Kangjiang1,2; Tong, Xiaogang1; Li, Tao1; Shi, Bingfei1; Wang, Haiyang1; Yan, Pengcheng3; Xia, Chengfeng1 |
| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2018-09-21 |
| 卷号 | 83期号:18页码:10948-10958 |
| ISSN号 | 0022-3263 |
| DOI | 10.1021/acs.joc.8b01597 |
| 英文摘要 | Nitroxides can absorb both ultraviolet (UV) and visible light, and their electron can be excited from the pi-bonding orbital to the antibonding pi* orbital or the n-bonding orbital to the antibonding pi* orbital, respectively. Despite the reported UV-induced hydrogen atom transfer (HAT) process, the potential of nitroxides for visible light-excited photosynthesis is underexplored. Here we demonstrate that nitroxide can convert indole to its radical through a visible light-induced HAT process. A chiral phosphoric acid-catalyzed cyclization of the in situ-formed imine radical, followed by trapping by another molecule of nitroxide, provides the product in high yield and enantioselectivity. To highlight the novelty and efficiency of this strategy, an asymmetric total synthesis of natural product (-)-verrupyrroloindoline was accomplished in 5 steps. |
| 资助项目 | National Natural Science Foundation of China[21572236] ; National Natural Science Foundation of China[21602194] ; Program for Changjiang Scholars and Innovative Research Team in University[IRT_17R94] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| 出版者 | AMER CHEMICAL SOC |
| WOS记录号 | WOS:000445713000028 |
| 资助机构 | National Natural Science Foundation of China ; Program for Changjiang Scholars and Innovative Research Team in University |
| 源URL | [http://ir.kib.ac.cn/handle/151853/62548]  |
| 专题 | 昆明植物研究所_植物化学与西部植物资源持续利用国家重点实验室 |
| 通讯作者 | Xia, Chengfeng |
| 作者单位 | 1.Yunnan Univ, Sch Chem Sci & Technol, Key Lab Med Chem Nat Resource, Minist Educ & Yunnan Prov, Kunming 650091, Yunnan, Peoples R China 2.Univ Chinese Acad Sci, Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China 3.Wenzhou Med Univ, Sch Pharmaceut Sci, Wenzhou 325035, Peoples R China |
| 推荐引用方式 GB/T 7714 | Liang, Kangjiang,Tong, Xiaogang,Li, Tao,et al. Enantioselective Radical Cyclization of Tryptamines by Visible Light-Excited Nitroxides[J]. JOURNAL OF ORGANIC CHEMISTRY,2018,83(18):10948-10958. |
| APA | Liang, Kangjiang.,Tong, Xiaogang.,Li, Tao.,Shi, Bingfei.,Wang, Haiyang.,...&Xia, Chengfeng.(2018).Enantioselective Radical Cyclization of Tryptamines by Visible Light-Excited Nitroxides.JOURNAL OF ORGANIC CHEMISTRY,83(18),10948-10958. |
| MLA | Liang, Kangjiang,et al."Enantioselective Radical Cyclization of Tryptamines by Visible Light-Excited Nitroxides".JOURNAL OF ORGANIC CHEMISTRY 83.18(2018):10948-10958. |
入库方式： OAI收割
来源：昆明植物研究所
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