title: A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF(3)SiMe(3) as a trifluoromethylating agent.
abstract: A general synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones is described. The fluoride-catalyzed nucleophilic addition of a trifluoromethyl (CF3) group generated from (trifluoromethyl)trimethylsilane (CF3SiMe3, Ruppert-Prakash reagent) to a masked maleic anhydride 1 (cyclopentadiene-maleic anhydride adduct) provides the corresponding adducts 2 with high stereoselectivity. The γ-trifluoromethyl α,β-unsaturated γ-butyrolactones 4 were obtained after treatment of the adducts 2 with Grignard reagents, followed by flash-vacuum pyrolysis.
authors: Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand. manat.poh@mahidol.ac.th.
authors: Chonticha
authors: C
authors: Masusai
authors: Darunee
authors: D
authors: Soorukram
authors: Chutima
authors: C
authors: Kuhakarn
authors: Patoomratana
authors: P
authors: Tuchinda
authors: Chaveng
authors: C
authors: Pakawatchai
authors: Saowanit
authors: S
authors: Saithong
authors: Vichai
authors: V
authors: Reutrakul
authors: Manat
authors: M
authors: Pohmakotr
mesh_terms: D015107:4-Butyrolactone / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: C523557:(trifluoromethyl)-trimethylsilane; D006845:Hydrocarbons, Fluorinated; D014297:Trimethylsilyl Compounds; D015107:4-Butyrolactone