Asymmetric Dearomatization of Indole Derivatives with N-Hydroxycarbamates Enabled by Photoredox Catalysis

doi:10.1002/anie.201911144

	Asymmetric Dearomatization of Indole Derivatives with N-Hydroxycarbamates Enabled by Photoredox Catalysis
	Cheng, Yuan-Zheng 1; Zhao, Qing-Ru1,2 ; Zhang, Xiao 1; You, Shu-Li1,2
	2019-10-24
发表期刊	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (IF:16.1[JCR-2023],16.2[5-Year])
ISSN	1433-7851
EISSN	1521-3773
发表状态	已发表
DOI	10.1002/anie.201911144
摘要	Dearomatization of indoles provides efficient synthetic routes for substituted indolines. In most cases, indoles serve as nucleophiles. Reported here is an asymmetric dearomatization reaction of indole derivatives that function as electrophiles. The combination of a photocatalyst and chiral phosphoric acid open to air unlocks the umpolung reactivity of indoles, enabling their dearomatization with N-hydroxycarbamates as nucleophiles. A variety of fused indolines bearing intriguing oxy-amines were constructed in excellent yields with moderate to high enantioselectivities. Mechanistic studies show that the realization of two sequential single-electron transfer oxidations of the indole derivatives is key, generating the configurationally biased carbocation species while providing the source of stereochemical induction. These results not only provide an efficient synthesis of enantioenriched indoline derivatives, but also offer a novel strategy for further designing asymmetric dearomatization reactions.
关键词	asymmetric synthesis dearomatization indoles photochemistry umpolung
收录类别	SCI ; SCIE ; EI ; IC ; CCR
语种	英语
资助项目	Shanghai Sailing Program[18YF1428900]
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000492067700001
出版者	WILEY-V C H VERLAG GMBH
WOS关键词	ANION PHASE-TRANSFER ; ENANTIOSELECTIVE SYNTHESIS ; PHOSPHORIC-ACID ; OXIDATIVE DEAROMATIZATION ; METAL CATALYSIS ; RECENT PROGRESS ; BRONSTED ACID ; PYRROLOINDOLINES ; CONSTRUCTION ; CYCLIZATION
原始文献类型	Article ; Early Access
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/80504
专题	物质科学与技术学院_特聘教授组_游书力组上海科技大学物质科学与技术学院_硕士生
通讯作者	Zhang, Xiao; You, Shu-Li
作者单位	1.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China 2.ShanghaiTech Univ, Sch Phys Sci & Technol, 100 Haike Rd, Shanghai 201210, Peoples R China
通讯作者单位	物质科学与技术学院
推荐引用方式 GB/T 7714	Cheng, Yuan-Zheng,Zhao, Qing-Ru,Zhang, Xiao,et al. Asymmetric Dearomatization of Indole Derivatives with N-Hydroxycarbamates Enabled by Photoredox Catalysis[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2019.
APA	Cheng, Yuan-Zheng,Zhao, Qing-Ru,Zhang, Xiao,&You, Shu-Li.(2019).Asymmetric Dearomatization of Indole Derivatives with N-Hydroxycarbamates Enabled by Photoredox Catalysis.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION.
MLA	Cheng, Yuan-Zheng,et al."Asymmetric Dearomatization of Indole Derivatives with N-Hydroxycarbamates Enabled by Photoredox Catalysis".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019).