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
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume83Issue:18Pages:10948-10958
AbstractNitroxides 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.
DOI10.1021/acs.joc.8b01597
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:000445713000028
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/62548
Collection植物化学与西部植物资源持续利用国家重点实验室
Corresponding AuthorXia, Chengfeng
Affiliation1.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
Recommended Citation
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.
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