Asymmetric Synthesis of beta-Indolyl Cyclopentanones and Cyclopentylamides with an All-Carbon Quaternary Stereocenter via Chiral Phosphoric Acid Catalyzed Friedel-Crafts Alkylation Reactions

doi:10.1021/acs.orglett.9b00963

	Asymmetric Synthesis of beta-Indolyl Cyclopentanones and Cyclopentylamides with an All-Carbon Quaternary Stereocenter via Chiral Phosphoric Acid Catalyzed Friedel-Crafts Alkylation Reactions
	Liu, Wei1,2 ; Rajkumar, Subramani1 ; Wu, Weihu1 ; Huang, Ziyu1 ; Yang, Xiaoyu1
	2019-05-17
发表期刊	ORGANIC LETTERS
ISSN	1523-7060
卷号	21 期号:10 页码:3563-3567
发表状态	已发表
DOI	10.1021/acs.orglett.9b00963
摘要	The asymmetric Friedel-Crafts alkylation reactions of indoles with beta-substituted cyclopentenimines enabled by chiral phosphoric acid catalysis has been developed, which affords adducts possessing an all-carbon stereocenter with high levels of enantioselectivities. Furthermore, the addition products could be readily converted into two types of useful but previously challenging chiral building blocks, such as beta-alkyl-beta-indolyl cyclopentanones and beta-alkyl-beta-indolyl cyclopentylamides, in one pot via in situ hydrolysis or reduction without erosion of chiral information.
收录类别	SCI ; SCIE ; IC ; CCR
语种	英语
资助项目	Shanghai Pujiang Program[17PJ1406300]
WOS研究方向	Chemistry
WOS类目	Chemistry, Organic
WOS记录号	WOS:000468696100020
出版者	AMER CHEMICAL SOC
WOS关键词	ENANTIOSELECTIVE CONSTRUCTION ; STEREOSELECTIVE CONSTRUCTION ; BRONSTED ACID ; FUNCTIONALIZATION ; ESTERS
原始文献类型	Article
引用统计
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/45563
专题	物质科学与技术学院_本科生物质科学与技术学院_PI研究组_杨晓瑜组物质科学与技术学院_硕士生
通讯作者	Yang, Xiaoyu
作者单位	1.ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
第一作者单位	物质科学与技术学院
通讯作者单位	物质科学与技术学院
第一作者的第一单位	物质科学与技术学院
推荐引用方式 GB/T 7714	Liu, Wei,Rajkumar, Subramani,Wu, Weihu,et al. Asymmetric Synthesis of beta-Indolyl Cyclopentanones and Cyclopentylamides with an All-Carbon Quaternary Stereocenter via Chiral Phosphoric Acid Catalyzed Friedel-Crafts Alkylation Reactions[J]. ORGANIC LETTERS,2019,21(10):3563-3567.
APA	Liu, Wei,Rajkumar, Subramani,Wu, Weihu,Huang, Ziyu,&Yang, Xiaoyu.(2019).Asymmetric Synthesis of beta-Indolyl Cyclopentanones and Cyclopentylamides with an All-Carbon Quaternary Stereocenter via Chiral Phosphoric Acid Catalyzed Friedel-Crafts Alkylation Reactions.ORGANIC LETTERS,21(10),3563-3567.
MLA	Liu, Wei,et al."Asymmetric Synthesis of beta-Indolyl Cyclopentanones and Cyclopentylamides with an All-Carbon Quaternary Stereocenter via Chiral Phosphoric Acid Catalyzed Friedel-Crafts Alkylation Reactions".ORGANIC LETTERS 21.10(2019):3563-3567.