Asymmetric Dearomatization of Indole Derivatives with N-Hydroxycarbamates Enabled by Photoredox Catalysis
Cheng, Yuan-Zheng1; Zhao, Qing-Ru1,2; Zhang, Xiao1; You, Shu-Li1,2
2019-10-24
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN1433-7851
Status已发表
DOI10.1002/anie.201911144
AbstractDearomatization 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.
Keywordasymmetric synthesis dearomatization indoles photochemistry umpolung
Indexed BySCI
Language英语
Funding ProjectShanghai Sailing Program[18YF1428900]
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000492067700001
PublisherWILEY-V C H VERLAG GMBH
EISSN1521-3773
WOS KeywordANION PHASE-TRANSFER ; ENANTIOSELECTIVE SYNTHESIS ; PHOSPHORIC-ACID ; OXIDATIVE DEAROMATIZATION ; METAL CATALYSIS ; RECENT PROGRESS ; BRONSTED ACID ; PYRROLOINDOLINES ; CONSTRUCTION ; CYCLIZATION
Original Document TypeArticle ; Early Access
Citation statistics
Cited Times:1[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://kms.shanghaitech.edu.cn/handle/2MSLDSTB/80504
Collection物质科学与技术学院_硕士生
物质科学与技术学院_特聘教授组_游书力组
Corresponding AuthorZhang, Xiao; You, Shu-Li
Affiliation1.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
Corresponding Author AffilicationSchool of Physical Science and Technology
Recommended Citation
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).
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