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Synthesis 1990; 1990(4): 347-350
DOI: 10.1055/s-1990-26874
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A Convenient Synthetic Route to Functionalized 5-Trifluoroacetyl-6-trifluoromethyl-3,4-dihydro-2H-pyrans: Hetero-Diels-Alder Reaction of β,β-Bis(trifluoroacetyl)vinyl Ethers with Electron-Rich Alkenes

Masaru Hojo* , Ryōichi Masuda, Etsuji Okada
  • *Department of Industrial Chemistry, Faculty of Engineering, Kobe University, Rokkodai, Nada, Kobe 657, Japan
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Publication Date:
17 September 2002 (online)

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Hetero-Diels-Alder reaction of β,β-bis(trifluoroacetyl)vinyl ethers, which are prepared by acylation of vinyl ethers with trifluoroacetic anhydride, with electron-rich alkenes such as vinyl ethers, ethyl vinyl sulfide and 1,1-diphenoxyethylene proceed quite easily under mild conditions to afford 2,4-dialkoxy-, 2-ethoxy-4-phenoxy-, 2-ethylthio-4-alkoxy-, 2,2-diphenoxy-4-ethoxy- and, 4-diaryloxy-5-trifluoroacetyl-6-trifluoromethyl-3,4dihydro-2H-pyrans in excellent yields.