N-Heterocyclic Carbene Catalytic [4+2] Cyclization of 3-Alkylenyloxindoles with Enals: gamma-Carbon Activation for Enantioselective Assembly of Spirocarbocyclic Oxindoles

doi:10.1021/acs.joc.6b01596

	N-Heterocyclic Carbene Catalytic [4+2] Cyclization of 3-Alkylenyloxindoles with Enals: gamma-Carbon Activation for Enantioselective Assembly of Spirocarbocyclic Oxindoles
	Yao, Hong 1,2,3; Zhou, Yu1 ; Chen, Xia 1,2,3; Zhang, Pengfei 1,2,3; Xu, Jinyi 2,3; Liu, Hong1,2,3
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2016-10-07
卷号	81 期号:19 页码:8888-8899
ISSN号	0022-3263
DOI	10.1021/acs.joc.6b01596
文献子类	Article
英文摘要	The ubiquitous structure of all-carbospirocyclic oxindoles makes the development of new methods for their enantioselective and stereoselective synthesis a significant ongoing challenge. Herein, we disclose a formal [4 + 2] annulation through N-heterocyclic carbene (NHC) catalysis for highly enantioselective synthesis of intriguing spirocarbocyclic oxindoles in the presence of Lewis acids. This protocol features good substrates tolerance, good yields, and excellent diastereoselectivities and enantioselectivities (up to 97% ee) under mild conditions.
资助项目	National Natural Science Foundation of China[21632008] ; National Natural Science Foundation of China[21472209] ; National Natural Science Foundation of China[21672232] ; National Natural Science Foundation of China[91229204] ; Major Project of Chinese National Programs for Fundamental Research and Development[2015CB910304] ; National Basic Research Program of China[2012CB518005] ; National S&T Major Projects[2013ZX09507-001] ; National S&T Major Projects[2014ZX09507002-001] ; China Pharmaceutical University[SKLNMZZCX201404]
WOS关键词	BOND-FORMING REACTIONS ; FORMAL 3+2 ANNULATION ; STEREOSELECTIVE-SYNTHESIS ; COOPERATIVE CATALYSIS ; BRONSTED ACID ; ASYMMETRIC-SYNTHESIS ; EFFICIENT SYNTHESIS ; KINETIC RESOLUTION ; ALKYNYL ALDEHYDES ; AZOMETHINE IMINES
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000385054300021
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/275863]
专题	药物化学研究室
通讯作者	Xu, Jinyi; Liu, Hong
作者单位	1.Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, 555 Chong Zhi Rd, Shanghai 201203, Peoples R China 2.China Pharmaceut Univ, State Key Lab Nat Med, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, Peoples R China; 3.China Pharmaceut Univ, Dept Med Chem, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, Peoples R China;
推荐引用方式 GB/T 7714	Yao, Hong,Zhou, Yu,Chen, Xia,et al. N-Heterocyclic Carbene Catalytic [4+2] Cyclization of 3-Alkylenyloxindoles with Enals: gamma-Carbon Activation for Enantioselective Assembly of Spirocarbocyclic Oxindoles[J]. JOURNAL OF ORGANIC CHEMISTRY,2016,81(19):8888-8899.
APA	Yao, Hong,Zhou, Yu,Chen, Xia,Zhang, Pengfei,Xu, Jinyi,&Liu, Hong.(2016).N-Heterocyclic Carbene Catalytic [4+2] Cyclization of 3-Alkylenyloxindoles with Enals: gamma-Carbon Activation for Enantioselective Assembly of Spirocarbocyclic Oxindoles.JOURNAL OF ORGANIC CHEMISTRY,81(19),8888-8899.
MLA	Yao, Hong,et al."N-Heterocyclic Carbene Catalytic [4+2] Cyclization of 3-Alkylenyloxindoles with Enals: gamma-Carbon Activation for Enantioselective Assembly of Spirocarbocyclic Oxindoles".JOURNAL OF ORGANIC CHEMISTRY 81.19(2016):8888-8899.