Fundamentals of AsymmeTric Organo CATalysis (ERC-STG: FASTO-CAT 2017-2023)
Asymmetric organo-catalysis represents a metal-free alternative to conventional asymmetric transition metal catalysis. These organo-catalysts emerged only in the recent decades and can provide high stereoselectivity. Therefore, they are particularly suited for the synthesis of biologically relevant molecules, where chirality is important for various functions, e.g. for the pharmaceutical activity of drugs. Despite the success of these organo-chemical routes, remarkably little is known about the reactive intermediates in a realistic environment. Since these intermediates, however, induce chirality in the first place, we experimentally quantify such reactive intermediates, and analyse their nature and geometry.
We study reactive intermediates using a combination of different spectroscopic methods: With ultrafast two-color and two-dimensional infrared spectroscopy we detect molecular vibrations, in order to trace changes in the molecules’ environment in real-time. By means of dielectric and NMR spectroscopy he investigate the electronic structure and binding motifs between the catalyst and the substrate. This combination of techniques thus allows probing molecular interactions on all timescales relevant to catalytic processes ranging from femtoseconds to seconds. Correlating the thus obtained information with the enantiomeric excess obtained in catalytic processes allows identifying the key elements that are required for stereocontrol. Such molecular-level insights will provide fundamental parameters for the optimization of reaction conditions and routes towards novel catalytic routes.
Optimizing catalysis as well as predicting new catalytic routes opens different fields of application for the asymmetric organo-catalysis. For example in medicine, one example may be a more efficient and targeted production of antimalarial medication.
