Synthesis of Chiral Trispirocyclic Oxindoles via Organic-Base/Au(I)-Catalyzed Sequential Reactions

doi:10.1021/acscatal.8b02157

	Synthesis of Chiral Trispirocyclic Oxindoles via Organic-Base/Au(I)-Catalyzed Sequential Reactions
	Guo, Wengang 1; Li, Lu 2; Ding, Qian 1; Lin, Xiangfeng 1; Liu, Xianghui 1; Wang, Kai 1; Liu, Yan 1; Fan, Hongjun 2; Li, Can 1
刊名	ACS CATALYSIS
	2018-11-01
卷号	8 期号:11 页码:10180-10189
关键词	asymmetric catalysis sequential reaction gold catalysis trispirocyclic framework hetero-Diels-Alder Reaction
ISSN号	2155-5435
DOI	10.1021/acscatal.8b02157
通讯作者	Liu, Yan(yanliu503@dicp.ac.cn) ; Fan, Hongjun(fanhj@dicp.ac.cn) ; Li, Can(canli@dicp.ac.cn)
英文摘要	Chiral spirooxindole is the core structure of a large number of natural and unnatural products with biological activities. However, the construction of trispirocyclic oxindoles remains challenging because of the difficulty in the assembly, the complex skeleton, and control of the stereoselectivities of the multiple quaternary stereocenters. Herein, we present the organic base/Au(I)-catalyzed sequential asymmetric 1,2-addition/cascade hydroamination/HDA/deisobutene reactions for the elaboration of various trispirocyclic N,O-ketal tethered oxindoles and bisoxindoles in excellent optical purities (91-99% ee). Key to the success of this methodology is Au(I)-catalyzed hetero-Diels Alder reactions utilizing N-Boc-iminooxindoles as the heterodienes.
资助项目	National Natural Science Foundation of China[21532006] ; National Natural Science Foundation of China[21472187] ; National Natural Science Foundation of China[21702203] ; Strategic Priority Research Program of the Chinese Academy of Sciences[XDB17000000]
WOS关键词	ISATIN-DERIVED KETIMINES ; DIELS-ALDER REACTION ; GOLD CATALYSIS ; ENANTIOSELECTIVE CONSTRUCTION ; RELAY CATALYSIS ; SPIROCYCLOPENTANE BIOXINDOLES ; ASYMMETRIC ORGANOCATALYSIS ; CONTIGUOUS STEREOCENTERS ; BIFUNCTIONAL CATALYST ; ISOTETRONIC ACIDS
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000449723900030
资助机构	National Natural Science Foundation of China ; National Natural Science Foundation of China ; Strategic Priority Research Program of the Chinese Academy of Sciences ; Strategic Priority Research Program of the Chinese Academy of Sciences ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Strategic Priority Research Program of the Chinese Academy of Sciences ; Strategic Priority Research Program of the Chinese Academy of Sciences ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Strategic Priority Research Program of the Chinese Academy of Sciences ; Strategic Priority Research Program of the Chinese Academy of Sciences ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Strategic Priority Research Program of the Chinese Academy of Sciences ; Strategic Priority Research Program of the Chinese Academy of Sciences
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/166674]
专题	大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者	Liu, Yan; Fan, Hongjun; Li, Can
作者单位	1.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China 2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China
推荐引用方式 GB/T 7714	Guo, Wengang,Li, Lu,Ding, Qian,et al. Synthesis of Chiral Trispirocyclic Oxindoles via Organic-Base/Au(I)-Catalyzed Sequential Reactions[J]. ACS CATALYSIS,2018,8(11):10180-10189.
APA	Guo, Wengang.,Li, Lu.,Ding, Qian.,Lin, Xiangfeng.,Liu, Xianghui.,...&Li, Can.(2018).Synthesis of Chiral Trispirocyclic Oxindoles via Organic-Base/Au(I)-Catalyzed Sequential Reactions.ACS CATALYSIS,8(11),10180-10189.
MLA	Guo, Wengang,et al."Synthesis of Chiral Trispirocyclic Oxindoles via Organic-Base/Au(I)-Catalyzed Sequential Reactions".ACS CATALYSIS 8.11(2018):10180-10189.