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.
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