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Sinteza in katalitska aktivnost organokatalizatorjev na osnovi N$^1$-((1R,2R)-2-(dimetilamino)cikloheksil)benzen-1,2-diaminov
ID Golob, Ana (Author), ID Grošelj, Uroš (Mentor) More about this mentor... This link opens in a new window

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Abstract
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.

Language:Slovenian
Keywords:asimetrična organokataliza, nekovalentni bifunkcionalni organokatalizatorji, Michaelova adicija, benzen-1, 2-diamin, derivati (1R, 2R)-cikloheksan-1, 2-diamina
Work type:Master's thesis/paper
Typology:2.09 - Master's Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2024
PID:20.500.12556/RUL-160089 This link opens in a new window
COBISS.SI-ID:205857539 This link opens in a new window
Publication date in RUL:19.08.2024
Views:113
Downloads:32
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Secondary language

Language:English
Title:Synthesis and catalytic activity of organocatalysts based on N$^1$-((1R,2R)-2-(dimethylamino)cyclohexyl)benzene-1,2-diamines
Abstract:
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.

Keywords:asymmetric organocatalysis, noncovalent bifunctional organocatalysts, Michael addition, benzene-1, 2-diamine, (1R, 2R)-cyclohexane-1, 2-diamine derivatives

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