Thesis supervisor: Antal Csámpai
Location of studies (in Hungarian): TTK Kémiai Intézet Abbreviation of location of studies: Kém.
Description of the research topic:
Recently the significance of organocatalytic methods continues to increase in asymmetric synthesis. The enantioselective organocatalytic versions of a number of fundamental functionalizations associated with the appearance of molecular chirality are extensively used in organic chemistry. One of the most widely used traditional acyl-transfer catalyst is 4-dimethylaminopyridine (DMAP) having considerably increased efficiency relatively to those produced by pyridine or other tertier amine bases. The acylations involving chiral components may also be accompanied by further elementary steps (e.g. formation of chiral ring systems) the efficient transfer of chiral information is of basic importance int he enantioselective versions of these transformations. The scarce reported examples of chiral acyl-transfer catalyst having structures analogue with DMAP belong to the group of fused ferrocene derivatives. Although these compounds proved to be efficient in promoting certain conversions, their synthesis proceeding through a long multistep pathway terminates with the resolvation of the enantiomers of the racemic products. Our group is currently working on the development of novel ferrocene-based acyl-transfer catalysts accessable by facile enantioselective synthetic methods without demanding resolvation procedures. As a continuation of this research we envisage the systematic extension, evaluation and modelling of further representatives of ferrocene-fused amidine bases with the elements of planar- and central chirality which have been successfully utilized so far in the kinetic resolvation of the racemic mixtures of a few secondary carbinol. On the basis of the studies to be accomplished we also expect to disclose structure-reactivity relationships necessary to design further catalysts of enhanced efficiency.