Aziridīn-2-karbonskābes esteru reakcijas ar litija diizopropilamīdu
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Latvijas Universitāte
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Abstract
Darbā izpētītas 1-alkiloksikarbonil-aziridīn-2-karbonskābes esteru reakcijas ar litija diizopropilamīdu. Tika konstatēts, ka deprotonējot 1-alkiloksi-aziridīn-2-karbonskābes esterus un alkilējot iegūtus anjonus nav iespējams iegūt četraizvietotus pie α-oglekļa atoma aziridīna atvasinājumus. Deprotonēšanas reakcijas rezultātā notiek acilgrupas migrācija no N uz C un veidojas aziridīn-2,2-dikarboksilāti. Darba eksperimentālajā daļā tika sintezēti dažādi simetriski un nesimetriski aziridīn-2,2-dikarboksilāti, kas satur hirālo centru molekulā. Īpaša uzmanība darbā ir veltīta reakcijas mehānisma pētījumiem. Tika pētīta reakcijas stereoselektivitāte, kā arī šķīdinātāja ietekme uz veidoto anjonu stabilitāti un reaģētspēju.
Reactions of 1-alkyloxycarbonyl-aziridine-2-carboxylic acid esters with lithium diisopropilamide are being studied. It was found, that it is not possible to obtain tetrasubstituted at the α-carbon aziridine derivatives in deprotonation and further alkylation of 1-alkyloxycarbonyl-aziridine-2-carboxylic acid esters. Acylgroup migration from N to C takes place in deprotonation reactions and, as a result, aziridine-2,2-dicarboxylates are formed. In the experimental part of research project were synthesized several symmetric and asymmetric aziridine-2,2-dicarboxylates with a chiral centre in the molecule. Especial attention is being paid to reaction mechanism studies. Reaction stereoselectivity and solvent influence on anion stability and reactivity were studied.
Reactions of 1-alkyloxycarbonyl-aziridine-2-carboxylic acid esters with lithium diisopropilamide are being studied. It was found, that it is not possible to obtain tetrasubstituted at the α-carbon aziridine derivatives in deprotonation and further alkylation of 1-alkyloxycarbonyl-aziridine-2-carboxylic acid esters. Acylgroup migration from N to C takes place in deprotonation reactions and, as a result, aziridine-2,2-dicarboxylates are formed. In the experimental part of research project were synthesized several symmetric and asymmetric aziridine-2,2-dicarboxylates with a chiral centre in the molecule. Especial attention is being paid to reaction mechanism studies. Reaction stereoselectivity and solvent influence on anion stability and reactivity were studied.