LICP OpenIR  > 羰基合成与选择氧化国家重点实验室(OSSO)
Asymmetric Synthesis of 2-Trifluoromethylated Spiro-pyrrolidine-3,3-oxindoles via Squaramide-Catalyzed Umpolung and 1,3-Dipolar Cycloaddition
DepartmentOSSO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 PublicationAdvanced Synthesis and Catalysis
ISSN1615-4150
Volume358Issue: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.

KeywordAsymmetric 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
DOI10.1002/adsc.201600688
Funding Organizationthe National Natural Science Foundation of China (Nos. 21432003;21272107;21272108;81260387;81360112;81573265)
Indexed BySCI
If5.646
Language英语
Funding Project日常管理与大型仪器组
compositor第二作者单位
Citation statistics
Cited Times:47[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://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 AuthorYan, Wenjin; Wang, Kairong; Wang R(王锐)
Affiliation1.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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