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Title: A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF<inf>3</inf>SiMe<inf>3</inf>as a trifluoromethylating agent
Authors: Chonticha Masusai
Darunee Soorukram
Chutima Kuhakarn
Patoomratana Tuchinda
Chaveng Pakawatchai
Saowanit Saithong
Vichai Reutrakul
Manat Pohmakotr
Mahidol University
Prince of Songkla University
Keywords: Biochemistry, Genetics and Molecular Biology;Chemistry
Issue Date: 14-Oct-2013
Citation: Organic and Biomolecular Chemistry. Vol.11, No.38 (2013), 6650-6658
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. © 2013 The Royal Society of Chemistry.
ISSN: 14770520
Appears in Collections:Scopus 2011-2015

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