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Synlett 1997; 1997(12): 1349-1350
DOI: 10.1055/s-1997-1038
DOI: 10.1055/s-1997-1038
letter
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A Novel Efficient Synthesis of Heteroaryl Substituted α,β-Unsaturated Trifluoromethyl Ketones
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
![](https://www.thieme-connect.de/media/synlett/199712/lookinside/thumbnails/10.1055-s-1997-1038-1.jpg)
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