Enantioselective Radical Cyclization of Tryptamines by Visible Light-Excited Nitroxides
Liang, Kangjiang1,2; Tong, Xiaogang1; Li, Tao1; Shi, Bingfei1; Wang, Haiyang1; Yan, Pengcheng3; Xia, Chengfeng1
2018-09-21
发表期刊JOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
卷号83期号:18页码:10948-10958
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.
资助信息National Natural Science Foundation of China; Program for Changjiang Scholars and Innovative Research Team in University
语种英语
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]
引用统计
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/62548
专题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
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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.
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