Publication: Synthesis of γ-difluoromethyl α,β-unsaturated γ-butyrolactones using PhSCF<inf>2</inf>SiMe<inf>3</inf>as a difluoromethylating agent
Issued Date
2015-06-01
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ISSN
10990690
1434193X
1434193X
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2-s2.0-85027919571
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Mahidol University
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SCOPUS
Bibliographic Citation
European Journal of Organic Chemistry. Vol.2015, No.17 (2015), 3751-3759
Suggested Citation
Arisara Issaree, Chonticha Masusai, Darunee Soorukram, Chutima Kuhakarn, Vichai Reutrakul, Manat Pohmakotr Synthesis of γ-difluoromethyl α,β-unsaturated γ-butyrolactones using PhSCF<inf>2</inf>SiMe<inf>3</inf>as a difluoromethylating agent. European Journal of Organic Chemistry. Vol.2015, No.17 (2015), 3751-3759. doi:10.1002/ejoc.201500342 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/35748
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Title
Synthesis of γ-difluoromethyl α,β-unsaturated γ-butyrolactones using PhSCF<inf>2</inf>SiMe<inf>3</inf>as a difluoromethylating agent
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Abstract
Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. The synthesis of γ-difluoromethyl α,β-unsaturated γ-butyrolactones using PhSCF2SiMe3(1) as a difluoromethylating agent is described. The method involves the fluoride-catalyzed nucleophilic addition of 1 to a masked maleic anhydride 2 (cyclopentadiene-maleic anhydride adduct) to give key adduct 3. This adduct can be converted into γ-difluoromethyl α,β-unsaturated γ-butyrolactones 6 through reductive cleavage of the phenylsulfanyl group, stereoselecive nucleophilic addition reaction with Grignard reagents, followed by flash-vacuum pyrolysis. A general synthesis of γ-difluoromethyl α,β-unsaturated γ-butyrolactones is described. The method involves the fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3to a masked maleic anhydride followed by reductive cleavage of the phenylsulfanyl group, reaction with Grignard reagents or NaBH4and flash-vacuum pyrolysis.