Enantioselective Radical Cyclization of Tryptamines by Visible Light-Excited Nitroxides

doi:10.1021/acs.joc.8b01597

	Enantioselective Radical Cyclization of Tryptamines by Visible Light-Excited Nitroxides
	Liang, Kangjiang 1,2; Tong, Xiaogang 1; Li, Tao 1; Shi, Bingfei 1; Wang, Haiyang 1; Yan, Pengcheng 3; Xia, Chengfeng 1
	2018-09-21
发表期刊	JOURNAL OF ORGANIC CHEMISTRY
ISSN	0022-3263
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.
DOI	10.1021/acs.joc.8b01597
语种	英语
WOS记录号	WOS:000445713000028
引用统计	被引频次：45[WOS] [WOS记录] [WOS相关记录]
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
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.