20.500.12556/RUL-160089 Sinteza in katalitska aktivnost organokatalizatorjev na osnovi N$^1$-((1R,2R)-2-(dimetilamino)cikloheksil)benzen-1,2-diaminov Synthesis and catalytic activity of organocatalysts based on N$^1$-((1R,2R)-2-(dimethylamino)cyclohexyl)benzene-1,2-diamines Asimetrična sinteza je zelo pomembna veja organske kemije. Enantiomerno čiste spojine se da pripraviti na različne načine, eden od pomembnejših pa je, predvsem zavoljo enostavnosti in dostopnosti, s pomočjo uporabe majhnih organskih molekul kot katalizatorjev. V svoji magistrski nalogi sem se osredotočila na pripravo novih kiralnih ogrodij na osnovi N$^1$-((1R,2R)-2(dimetilamino)cikloheksil)benzen-1,2-diamina in njihovo kasnejšo pretvorbo do nekovalentnih bifunkcionalnih organokatalizatorjev. Pri pripravi kiralnih ogrodij sem izhajala iz komercialno dostopnega (1R,2R)-cikloheksan-1,2-diamina ter 1-fluoro-2-nitrobenzena in njegovih derivatov, ki sem ju združila z reakcijo nukleofilne aromatske substitucije. Sledilo je alkiliranje aminske skupine do dimetilaminske skupine ter redukcija nitro skupine v aminsko skupino. Prosto aminsko skupino pripravljenih gradnikov sem funkcionalizirala do želenih organokatalizatorjev z reakcijami reduktivnega alkiliranja, sulfoniranja, aciliranja in križnega spajanja. Učinkovitost pripravljenih organokatalizatorjev sem preizkusila z modelno reakcijo Michaelove adicije acetilacetona na trans-β-nitrostiren; produkt adicije je nastal z do 93 % konverzijo in do 41 % enantiomernim presežkom. Asymmetric synthesis has become a very important part of organic chemistry. Enantiomerically pure compounds can be prepared in various ways, one of the most important, especially due to its simplicity and accessibility, being through the use of small organic molecules as catalysts. In my master's thesis, I focused on the preparation of new chiral scaffolds based on N$^1$-((1R,2R)-2(dimethylamino)cyclohexyl)benzene-1,2-diamine and their subsequent conversion into non-covalent bifunctional organocatalysts. In the preparation of chiral scaffolds, I started from commercially available (1R,2R)-cyclohexane-1,2-diamine and 1-fluoro-2-nitrobenzene and its derivatives, which I combined with a nucleophilic aromatic substitution reaction. This was followed by alkylation of the amine group to the dimethylamine group and the reduction of the nitro group to the amine group. The free amine group of the prepared scaffolds was functionalized to the desired organocatalysts through reactions of reductive alkylation, sulfonation, acylation, and cross-coupling. The efficiency of the prepared organocatalysts was tested in a model reaction of Michael addition of acetylacetone to trans-β-nitrostyrene; the addition product was formed in up to 93% conversion and up to 41% enantiomeric excess. asimetrična organokataliza nekovalentni bifunkcionalni organokatalizatorji Michaelova adicija benzen-1 2-diamin derivati (1R 2R)-cikloheksan-1 2-diamina asymmetric organocatalysis noncovalent bifunctional organocatalysts Michael addition benzene-1 2-diamine (1R 2R)-cyclohexane-1 2-diamine derivatives true false false Slovenski jezik Angleški jezik Magistrsko delo/naloga 2024-08-19 11:00:16 2024-08-19 11:00:26 2024-08-30 09:43:01 0000-00-00 00:00:00 2024 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 23067 205857539 Golob_Ana_-_Sinteza_in_katalitska_aktivnost_organokatalizatorjev_na_osnovi_N1-((1R,2R)-2-(dimeti.pdf Golob_Ana_-_Sinteza_in_katalitska_aktivnost_organokatalizatorjev_na_osnovi_N1-((1R,2R)-2-(dimeti.pdf 1 244E56DC92D78C3FCA5D1C18BFD84D57 3ab0415befd6341eaaaab2a357ed68fc187e76de1c20787a4abbf3360886419a 4d21f6c1-5e09-11ef-8f74-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=188543 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0