V. Sukach, V. Tkachuk, V. Shoba
Mar 1, 2014
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Influential Citations
14
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Journal
European Journal of Organic Chemistry
Abstract
The reactions of variously substituted 4-(trifluoromethyl)pyrimidin-2(1H)-ones with acetone in the presence of L-proline or chiral secondary amine organocatalysts were studied. As demonstrated, 4-(trifluoromethyl)pyrimidin-2(1H)-ones unsubstituted at the 6-position of the heterocyclic ring react with acetone at the endocyclic C=N or C=C bond depending on whether thermodynamic or kinetic control is operative in the addition reaction and also depending on the catalyst used. Racemic kinetically preferred regioisomers, 6-(2-oxopropyl)-4-(trifluoromethyl)-3,4-dihydropyrimidin-2(1H)-ones, were found to undergo intermolecular organocatalytic rearrangement into enantioenriched thermodynamically stable products, 4-(2-oxopropyl)-4-(trifluoromethyl)-3,4-dihydropyrimidin-2(1H)-ones, with enantiomeric ratios up to 83:17.