南方科技大学知识苑(SUSTech KC): Atroposelective Synthesis of 2-Arylindoles via Chiral Phosphoric Acid-Catalyzed Direct Amination of Indoles†

题名	Atroposelective Synthesis of 2-Arylindoles via Chiral Phosphoric Acid-Catalyzed Direct Amination of Indoles†
作者	Bao，Wen 1,2; Chen，Ye Hui2 ; Liu，Yu Wei2 ; Xiang，Shao Hua2 ; Tan，Bin2
通讯作者	Tan，Bin
发表日期	2024-04-01
DOI	10.1002/cjoc.202300589
发表期刊	Chinese Journal of Chemistry 影响因子和分区
ISSN	1001-604X
EISSN	1614-7065
卷号	42 期号:7页码:731-735
摘要	Indole-based atropisomers are a very important class of axially chiral compounds. However, the atroposelective synthesis of axially chiral 2-arylindole remains largely unexplored. In this study, we report the successful synthesis of atropisomeric 2-arylindoles using direct amination of indoles with p-quinonediimines in the presence of chiral phosphoric acid as a catalyst. Quinonediimine acts as an aminating reagent through formal polarity inversion of imine. The malonate group on the 2-aryl of 2-indoles was found to be essential for high enantioselectivity of the products. This could be due to the additional interaction between the ester group and the catalyst, as well as the intramolecular hydrogen bonding. Our findings provide a new strategy for the asymmetric construction of 2-arylindole atropisomers.
关键词	Asymmetric catalysis Atroposelective synthesis Axially chiral 2-arylindole Chiral phosphoric acid Direct amination Enantioselectivity Nucleophilic addition Quinonediimines
相关链接	[Scopus记录]
收录类别	SCI
语种	英语
学校署名	通讯
ESI学科分类	CHEMISTRY
Scopus记录号	2-s2.0-85182862985
来源库	Scopus
引用统计	被引频次[WOS]：10
成果类型	期刊论文
条目标识符	http://sustech.caswiz.com/handle/2SGJ60CL/729116
专题	理学院_化学系深圳格拉布斯研究院
作者单位	1.School of Pharmacy & State Key Laboratory of Applied Organic Chemistry,Lanzhou University,Lanzhou,Gansu,730000,China 2.Shenzhen Grubbs Institute,Department of Chemistry,Southern University of Science and Technology,Shenzhen,Guangdong,518055,China
第一作者单位	化学系; 深圳格拉布斯研究院
通讯作者单位	化学系; 深圳格拉布斯研究院
推荐引用方式 GB/T 7714	Bao，Wen,Chen，Ye Hui,Liu，Yu Wei,等. Atroposelective Synthesis of 2-Arylindoles via Chiral Phosphoric Acid-Catalyzed Direct Amination of Indoles†[J]. Chinese Journal of Chemistry,2024,42(7):731-735.
APA	Bao，Wen,Chen，Ye Hui,Liu，Yu Wei,Xiang，Shao Hua,&Tan，Bin.(2024).Atroposelective Synthesis of 2-Arylindoles via Chiral Phosphoric Acid-Catalyzed Direct Amination of Indoles†.Chinese Journal of Chemistry,42(7),731-735.
MLA	Bao，Wen,et al."Atroposelective Synthesis of 2-Arylindoles via Chiral Phosphoric Acid-Catalyzed Direct Amination of Indoles†".Chinese Journal of Chemistry 42.7(2024):731-735.