Chonticha MasusaiDarunee SoorukramChutima KuhakarnPatoomratana TuchindaChaveng PakawatchaiSaowanit SaithongVichai ReutrakulManat PohmakotrMahidol UniversityPrince of Songkla University2018-10-192018-10-192013-10-14Organic and Biomolecular Chemistry. Vol.11, No.38 (2013), 6650-6658147705202-s2.0-84884179676https://repository.li.mahidol.ac.th/handle/20.500.14594/31190A 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. © 2013 The Royal Society of Chemistry.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryArticleSCOPUS10.1039/c3ob41247d