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

Issued Date

2013-10-14

Resource Type

Article

ISSN

14770520

DOI

10.1039/c3ob41247d

Other identifier(s)

2-s2.0-84884179676

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Organic and Biomolecular Chemistry. Vol.11, No.38 (2013), 6650-6658

Suggested Citation

Chonticha Masusai, Darunee Soorukram, Chutima Kuhakarn, Patoomratana Tuchinda, Chaveng Pakawatchai, Saowanit Saithong, Vichai Reutrakul, Manat Pohmakotr A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF<inf>3</inf>SiMe<inf>3</inf>as a trifluoromethylating agent. Organic and Biomolecular Chemistry. Vol.11, No.38 (2013), 6650-6658. doi:10.1039/c3ob41247d Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/31190

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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

Author(s)

Chonticha Masusai
 Darunee Soorukram
 Chutima Kuhakarn
 Patoomratana Tuchinda
 Chaveng Pakawatchai
 Saowanit Saithong
 Vichai Reutrakul
 Manat Pohmakotr

Other Contributor(s)

Mahidol University
 Prince of Songkla University

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.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry

Availability

URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/31190

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