title: Synthesis of CF3-containing 3,3'-cyclopropyl spirooxindoles by sequential [3 + 2] cycloaddition/ring contraction of ylideneoxindoles with 2,2,2-trifluorodiazoethane.
abstract: A [3 + 2] cycloaddition/ring contraction sequence of ylideneoxindoles with in situ-generated 2,2,2-trifluorodiazoethane without the use of any transition-metal catalyst has been developed. The reaction provides efficient access to biologically important and synthetically useful CF3-containing 3,3'-cyclopropyl spirooxindoles in high yield (74-99%) with high diastereoselectivity (>95:5 d.r.).
authors: Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University , 152 Luoyu Road, Wuhan, Hubei 430079, China.
authors: Tian-Ren
authors: TR
authors: Li
authors: Shu-Wen
authors: SW
authors: Duan
authors: Wei
authors: W
authors: Ding
authors: Yi-Yin
authors: YY
authors: Liu
authors: Jia-Rong
authors: JR
authors: Chen
authors: Liang-Qiu
authors: LQ
authors: Lu
authors: Wen-Jing
authors: WJ
authors: Xiao
mesh_terms: D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000592527:2,2,2-trifluorodiazoethane; D001391:Azo Compounds; D006845:Hydrocarbons, Fluorinated; D007211:Indoles; D013141:Spiro Compounds