Control of Regio- and Enantioselectivity in the Asymmetric Organocatalytic Addition of Acetone to 4-(Trifluoromethyl)pyrimidin-2(1H)-ones

Autor:	Eduard B. Rusanov, Viktor M. Tkachuk, Veronika M. Shoba, M. V. Vovk, Gerd-Volker Röschenthaler, V. V. Pirozhenko, Volodymyr A. Sukach, Alexey A. Chekotilo
Rok vydání:	2014
Předmět:	chemistry.chemical_compound Addition reaction Trifluoromethyl chemistry Organic Chemistry Acetone Structural isomer Enantioselective synthesis Organic chemistry Regioselectivity Amine gas treating Physical and Theoretical Chemistry Enantiomer
Zdroj:	European Journal of Organic Chemistry. 2014:1452-1460
ISSN:	1434-193X
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8ee3ff12f90592244f6dd4371628e738 https://doi.org/10.1002/ejoc.201301542 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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