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Synlett 1997; 1997(12): 1349-1350
DOI: 10.1055/s-1997-1038
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A Novel Efficient Synthesis of Heteroaryl Substituted α,β-Unsaturated Trifluoromethyl Ketones

Valentine G. Nenajdenko1 , Arkady L. Krasovsky, Mikhail V. Lebedev, Elizabeth S. Balenkova2
  • 1Department of Chemistry, Moscow State University, 119899 Moscow, Russia, Fax +7-(095)-932-88-46; E-mail: Nen@acylium.chem.msu.su
  • 2Department of Chemistry, Moscow State University, 119899 Moscow, Russia, Fax +7-(095)-932-88-46
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Publication Date:
31 December 2000 (online)

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A synthesis of a novel electrophilic reagent 1,1,1-trifluoro-4-(phenylsulfonyl)-but-3-ene-2,2-diol 2 is described. The reaction of 2 with various electron-rich heteroaromatics such as furans, pyrroles, indoles is investigated. The addition-elimination reaction proceeds under mild conditions stereospecifically and permits a novel one-step procedure for the preparation of trifluoroacetylvinyl substituted heterocycles in high yield. In all cases only E-isomers of unsaturated CF3 ketones were obtained.

1,1,1-trifluoro-4-(phenylsulfonyl)-3-butene-2,2-diol - α,β-unsaturated CF3 ketones - electrophilic substitution - addition-elimination reaction