Abstract
Chemo- and stereoselectivity of the reaction of 1-[2-(vinyloxy)ethyl]-1H-pyrroles with trifluoroacetic anhydride have been studied. The reaction with an equimolar amount of trifluoroacetic anhydride chemoselectively involves the free α-position of the pyrrole ring with formation of the corresponding α-trifluoroacetylpyrroles. In the reaction with 2 equiv of trifluoroacetic anhydride, acylation of both α-position of the pyrrole ring and β-position of the vinyloxy group leads to the formation of 1-(2-{[(1E)-4,4,4-trifluoro-3-oxobut-1-en-1-yl]oxy}ethyl)-2-trifluoroacetyl derivatives with high stereoselectivity.
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Original Russian Text © E.Kh. Sadykov, N.A. Lobanova, V.K. Stankevich, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 4, pp. 547–551.
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Sadykov, E.K., Lobanova, N.A. & Stankevich, V.K. Reaction of 1-[2-(vinyloxy)ethyl]-1H-pyrroles with trifluoroacetic anhydride. Russ J Org Chem 52, 533–537 (2016). https://doi.org/10.1134/S1070428016040096
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DOI: https://doi.org/10.1134/S1070428016040096