Asymmetric Synthesis of 2-Trifluoromethylated Spiro-pyrrolidine-3,3-oxindoles via Squaramide-Catalyzed Umpolung and 1,3-Dipolar Cycloaddition | |
Department | OSSO国家重点实验室 |
Su, Jinhuan1; Ma, Zelin1; Li, Xiaoyuan1; Lin, Li1; Shen ZQ(沈志强)2; Yang PJ(杨培菊)2; Li, Yuan3; Wang, Hailin3; Yan, Wenjin1; Wang, Kairong1; Wang R(王锐)1,2; Wang R(王锐) | |
2016 | |
Source Publication | Advanced Synthesis and Catalysis |
ISSN | 1615-4150 |
Volume | 358Issue:23Pages:3777-3785 |
Abstract | The introduction of a trifluoromethyl group into the 2′-position of spiro-pyrrolidine-3,3′-oxindoles is described. By using 1 mol% of a quinine-derived squaramide as catalyst, the 2,2,2-trfluoroethylamine (CF3CH2NH2)-derived ketimine is transformed initially into a trifluoromethylimine through an umpolung reaction. The subsequent 1,3-dipolar cycloaddition gives the pharmaceutical important target compounds in excellent yields, enantioselectivities and diastereoselectivies. |
Keyword | Asymmetric Synthesis 1 Trifluoromethyl-containing Compounds 3-dipolar Cycloaddition Spiro-pyrrolidine-3 Umpolung Reaction 3'-oxindoles |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1002/adsc.201600688 |
Funding Organization | the National Natural Science Foundation of China (Nos. 21432003;21272107;21272108;81260387;81360112;81573265) |
Indexed By | SCI |
If | 5.646 |
Language | 英语 |
Funding Project | 日常管理与大型仪器组 |
compositor | 第二作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/21207 |
Collection | 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Yan, Wenjin; Wang, Kairong; Wang R(王锐) |
Affiliation | 1.Lanzhou Univ, Inst Pharmacol, Sch Basic Med Sci, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Peoples R China 2.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China 3.Peoples Hosp Gansu Prov, Lanzhou 730000, Peoples R China |
Recommended Citation GB/T 7714 | Su, Jinhuan,Ma, Zelin,Li, Xiaoyuan,et al. Asymmetric Synthesis of 2-Trifluoromethylated Spiro-pyrrolidine-3,3-oxindoles via Squaramide-Catalyzed Umpolung and 1,3-Dipolar Cycloaddition[J]. Advanced Synthesis and Catalysis,2016,358(23):3777-3785. |
APA | Su, Jinhuan.,Ma, Zelin.,Li, Xiaoyuan.,Lin, Li.,Shen ZQ.,...&王锐.(2016).Asymmetric Synthesis of 2-Trifluoromethylated Spiro-pyrrolidine-3,3-oxindoles via Squaramide-Catalyzed Umpolung and 1,3-Dipolar Cycloaddition.Advanced Synthesis and Catalysis,358(23),3777-3785. |
MLA | Su, Jinhuan,et al."Asymmetric Synthesis of 2-Trifluoromethylated Spiro-pyrrolidine-3,3-oxindoles via Squaramide-Catalyzed Umpolung and 1,3-Dipolar Cycloaddition".Advanced Synthesis and Catalysis 358.23(2016):3777-3785. |
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LZ01029653.pdf(1375KB) | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Application Full Text |
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