Synergetic Tandem Enantiomeric Enrichment in Catalytic Asymmetric Multi-Component Reactions (AMCRs): Highly Enantioselective Construction of Tetracyclic Indolines with Four Continuous Stereocenters

doi:10.1021/acscatal.8b00866

	Synergetic Tandem Enantiomeric Enrichment in Catalytic Asymmetric Multi-Component Reactions (AMCRs): Highly Enantioselective Construction of Tetracyclic Indolines with Four Continuous Stereocenters
	Kuang, Xiao-Kang1 ; Zhu, Jun 2; Zhou, Li 2; Wang, Lijia 2; Wang, Sunewang R.2; Tang, Yong1,2,3
	2018-06
发表期刊	ACS CATALYSIS (IF:11.3[JCR-2023],12.6[5-Year])
ISSN	2155-5435
卷号	8 期号:6 页码:4991-4995
发表状态	已发表
DOI	10.1021/acscatal.8b00866
摘要	Tetracyclic indolines are ubiquitous skeletons in bioactive natural products and pharmaceuticals, and efficient methods for their enantioselective synthesis are highly desired. Here, we report an efficient three-component formal [2 + 2 + 2] cycloaddition reaction between indoles, 2,3-dihydropyran, and methylene malonates for rapid construction of optically active tetracyclic indolines bearing four continuous stereocenters. Although the optimal catalyst Cu(II)/BOX displays only moderate enantioselectivities in either formal cyclobutanation or [4 + 2] cycloaddition reaction with donor acceptor cyclobutanes bearing a nonracemizable stereocenter, the collaborative tandem enantiomeric enrichment in the one-pot asymmetric multicomponent reaction is highly effective, thereby affording a wide range of tetracyclic indoline derivatives with excellent diastereo- and enantioselectivities in high yields.
关键词	copper catalysis asymmetric multicomponent reaction indolines D-A cyclobutanes cycloaddition
收录类别	SCI ; SCIE ; EI
语种	英语
资助项目	Natural Science Foundation of Shanghai[17ZR1436900]
WOS研究方向	Chemistry
WOS类目	Chemistry, Physical
WOS记录号	WOS:000434369600027
出版者	AMER CHEMICAL SOC
EI入藏号	20182305287333
EI主题词	Copper compounds ; Cycloaddition ; Enantiomers
EI分类号	Physical Chemistry:801.4 ; Chemical Reactions:802.2
WOS关键词	DONOR-ACCEPTOR CYCLOBUTANES ; FORMAL 4+2 CYCLOADDITION ; ORGANIC-SYNTHESIS ; STRATEGY ; DERIVATIVES ; STRYCHNINE ; ALKALOIDS ; INDOLES ; CYCLOPROPANES ; ALDEHYDES
原始文献类型	Article
引用统计	被引频次：51[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/23085
专题	物质科学与技术学院物质科学与技术学院_特聘教授组_唐勇组物质科学与技术学院_硕士生
通讯作者	Tang, Yong
作者单位	1.ShanghaiTech Univ, Sch Phys Sci & Technol, 393 Middle Huaxia Rd, Shanghai 201210, Peoples R China 2.Univ Chinese Acad Sci, Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China 3.Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, 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	Kuang, Xiao-Kang,Zhu, Jun,Zhou, Li,et al. Synergetic Tandem Enantiomeric Enrichment in Catalytic Asymmetric Multi-Component Reactions (AMCRs): Highly Enantioselective Construction of Tetracyclic Indolines with Four Continuous Stereocenters[J]. ACS CATALYSIS,2018,8(6):4991-4995.
APA	Kuang, Xiao-Kang,Zhu, Jun,Zhou, Li,Wang, Lijia,Wang, Sunewang R.,&Tang, Yong.(2018).Synergetic Tandem Enantiomeric Enrichment in Catalytic Asymmetric Multi-Component Reactions (AMCRs): Highly Enantioselective Construction of Tetracyclic Indolines with Four Continuous Stereocenters.ACS CATALYSIS,8(6),4991-4995.
MLA	Kuang, Xiao-Kang,et al."Synergetic Tandem Enantiomeric Enrichment in Catalytic Asymmetric Multi-Component Reactions (AMCRs): Highly Enantioselective Construction of Tetracyclic Indolines with Four Continuous Stereocenters".ACS CATALYSIS 8.6(2018):4991-4995.