Thiourea-catalyzed asymmetric domino Michael-cyclization reaction of 3-isothiocyanato oxindoles with beta,gamma-unsaturated alpha-keto esters for the synthesis of spirocyclic oxindoles

doi:10.1016/j.tet.2019.02.036

	Thiourea-catalyzed asymmetric domino Michael-cyclization reaction of 3-isothiocyanato oxindoles with beta,gamma-unsaturated alpha-keto esters for the synthesis of spirocyclic oxindoles
	Yuan, Wei-Cheng 1; Xu, Xiao-Ying ; Cui, Bao-Dong 2; Chen, Yong-Zheng 2; Bai, Mei 2
刊名	TETRAHEDRON
	2019-04-05
卷号	75 期号:14 页码:2155-2161
关键词	3-Isothiocyanato oxindoles beta,gamma-unsaturated alpha-keto esters Spirocyclic oxindoles
ISSN号	0040-4020
DOI	10.1016/j.tet.2019.02.036
通讯作者	Chen, Yong-Zheng() ; Yuan, Wei-Cheng(yuanwc@cioc.ac.cn)
英文摘要	A reaction between 3-isothiocyanato oxindoles and beta,gamma-unsaturated alpha-keto esters catalyzed by a chiral thiourea organocatalyst via a domino Michael-cyclization process is described, which delivers a range of biologically important 2'-thioxospiro[indoline-3,4'-oxazolidin]-2-one compounds in high yields with good diastereo- and enantioselectivities (up to 99% yield, >99:1 dr, >99% ee). Moreover, two of 2'-thioxospiro[indoline-3,4'-oxazolidin]-2-one compounds were found to significantly behave in antiinflammatory activities in a preliminary biological evaluation. (C) 2019 Published by Elsevier Ltd.
资助项目	National Natural Science Foundation of China[21871252] ; National Natural Science Foundation of China[21572223] ; Science and Technology Department of Guizhou Province[QKHJZ-LKZ-2013-27] ; National First-Rate Construction of Guizhou Province (Pharmacy)[YDUCJS-YX-04] ; Program for Outstanding Youth of Zunyi Medical University[17zy-005]
WOS关键词	DIELS-ALDER REACTION ; HIGHLY ENANTIOSELECTIVE SYNTHESIS ; 4+2 CYCLOADDITIONS ; CASCADE REACTION ; EFFICIENT SYNTHESIS ; ALDOL-CYCLIZATION ; SIMPLE OLEFINS ; ALDEHYDES ; SPIROOXINDOLES ; CONSTRUCTION
WOS研究方向	Chemistry
语种	英语
出版者	PERGAMON-ELSEVIER SCIENCE LTD
WOS记录号	WOS:000463311400010
资助机构	National Natural Science Foundation of China ; National Natural Science Foundation of China ; Science and Technology Department of Guizhou Province ; Science and Technology Department of Guizhou Province ; National First-Rate Construction of Guizhou Province (Pharmacy) ; National First-Rate Construction of Guizhou Province (Pharmacy) ; Program for Outstanding Youth of Zunyi Medical University ; Program for Outstanding Youth of Zunyi Medical University ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Science and Technology Department of Guizhou Province ; Science and Technology Department of Guizhou Province ; National First-Rate Construction of Guizhou Province (Pharmacy) ; National First-Rate Construction of Guizhou Province (Pharmacy) ; Program for Outstanding Youth of Zunyi Medical University ; Program for Outstanding Youth of Zunyi Medical University
内容类型	期刊论文
源URL	[http://210.75.237.14/handle/351003/29654]
专题	中国科学院成都生物研究所
通讯作者	Yuan, Wei-Cheng; Chen, Yong-Zheng
作者单位	1.Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Sichuan, Peoples R China 2.Zunyi Med Univ, Sch Pharm, Gener Drug Res Ctr Guizhou Prov, Green Pharmaceut Engn Res Ctr Guizhou Prov, Zunyi 563000, Peoples R China
推荐引用方式 GB/T 7714	Yuan, Wei-Cheng,Xu, Xiao-Ying,Cui, Bao-Dong,et al. Thiourea-catalyzed asymmetric domino Michael-cyclization reaction of 3-isothiocyanato oxindoles with beta,gamma-unsaturated alpha-keto esters for the synthesis of spirocyclic oxindoles[J]. TETRAHEDRON,2019,75(14):2155-2161.
APA	Yuan, Wei-Cheng,Xu, Xiao-Ying,Cui, Bao-Dong,Chen, Yong-Zheng,&Bai, Mei.(2019).Thiourea-catalyzed asymmetric domino Michael-cyclization reaction of 3-isothiocyanato oxindoles with beta,gamma-unsaturated alpha-keto esters for the synthesis of spirocyclic oxindoles.TETRAHEDRON,75(14),2155-2161.
MLA	Yuan, Wei-Cheng,et al."Thiourea-catalyzed asymmetric domino Michael-cyclization reaction of 3-isothiocyanato oxindoles with beta,gamma-unsaturated alpha-keto esters for the synthesis of spirocyclic oxindoles".TETRAHEDRON 75.14(2019):2155-2161.