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

文献类型：期刊论文

作者Yao, Hong1,2,3; Zhou, Yu1; Chen, Xia1,2,3; Zhang, Pengfei1,2,3; Xu, Jinyi2,3; Liu, Hong1,2,3
刊名JOURNAL OF ORGANIC CHEMISTRY
出版日期2016-10-07
卷号81期号:19页码:8888-8899
ISSN号0022-3263
DOI10.1021/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.
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
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研究方向Chemistry
语种英语
出版者AMER CHEMICAL SOC
WOS记录号WOS:000385054300021
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.

入库方式： OAI收割

来源：上海药物研究所

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