Synthesis of new chiral mono-, di-, tri-, and tetraalkylglycolurils |
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| Authors: | A N Kravchenko A S Sigachev E Yu Maksareva G A Gazieva N S Trunova B V Lozhkin T S Pivina M M Il’in K A Lyssenko Yu V Nelyubina V A Davankov O V Lebedev N N Makhova V A Tartakovsky |
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| Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation;(2) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation |
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| Abstract: | Two general procedures were developed for the synthesis of chiral N-mono-, N, N′-di-, N, N′ N″-tri-, and N, N′, N″, N′″-tetraalkylglycolurils based on the reactions of 4,5-dihydroxy-imidazolidin-2-ones or glyoxal with one or two moles of alkylureas, respectively, by acid catalysis. The reactions of N-monoalkyl- and N, N′-dialkylureas with glyoxal proceed regioselectively. The mechanism of these reactions was suggested and partly confirmed by quantum-chemical calculations and experimental data. The enantiomeric separation of some chiral glycolurils by chiral-phase HPLC was carried out for the first time.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 680–692, March, 2005. |
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| Keywords: | glycolurils chirality 4 5-dihydroxyimidazolidin-2-ones mono- and dialkyl-ureas quantum-chemical calculations enantiomeric analysis and separation regioselectivity |
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