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A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF(3)SiMe(3) as a trifluoromethylating agent.

Authors
  • Masusai, Chonticha
  • Soorukram, Darunee
  • Kuhakarn, Chutima
  • Tuchinda, Patoomratana
  • Pakawatchai, Chaveng
  • Saithong, Saowanit
  • Reutrakul, Vichai
  • Pohmakotr, Manat
Type
Published Article
Journal
Organic & Biomolecular Chemistry
Publisher
The Royal Society of Chemistry
Publication Date
Oct 14, 2013
Volume
11
Issue
38
Pages
6650–6658
Identifiers
DOI: 10.1039/c3ob41247d
PMID: 23965759
Source
Medline
License
Unknown

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.

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