A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF<inf>3</inf>SiMe<inf>3</inf>as a trifluoromethylating agent

A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF<inf>3</inf>SiMe<inf>3</inf>as a trifluoromethylating agent

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-ma...

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Bibliographic Details
Main Authors: Chonticha Masusai, Darunee Soorukram, Chutima Kuhakarn, Patoomratana Tuchinda, Chaveng Pakawatchai, Saowanit Saithong, Vichai Reutrakul, Manat Pohmakotr
Other Authors: Mahidol University
Format: Article
Published: 2018
Subjects:
Biochemistry, Genetics and Molecular Biology
Chemistry
Online Access:https://repository.li.mahidol.ac.th/handle/123456789/31190
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Summary: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.

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