The use of small chiral organic molecules as catalysts for enantioselective reactions has led to a breakthrough in the field of asymmetric catalysis in the last decade. Their robustness and ease of use in reactions allow us to prepare new chiral compounds, while the preparation of new chiral organocatalysts is key to the further development of the field.
The central aim of the master's thesis was the synthesis of 1,2-benzenediamine derivatives of (1R,2R)-2-(piperidin-1-yl)cyclohexan-1-amine as chiral scaffolds for the subsequent synthesis of several new potential noncovalent bifunctional organocatalysts. The synthesis was based on commercially available (1R,2R)-cyclohexane-1,2-diamine and o-fluoronitrobenzene derivatives. The initially prepared 1,2-benzenediamine building blocks with a primary amino group were functionalized by selective derivatization of the free primary amino group to give the desired types of organocatalysts. All new compounds were fully characterized. The prepared organocatalysts were tested in a model Michael addition between acetylacetone and trans-ß-nitrostyrene.
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