CORDIS - Forschungsergebnisse der EU

Self-Amplifying Stereodynamic Catalysts in Enantioselective Catalysis


Think about an enantioselective catalyst, which can switch its enantioselectivity and which can be imprinted and provides self-amplification by its own chiral reaction product. Think about a catalyst, which can be fine-tuned for efficient stereoselective synthesis of drugs and other materials, e.g. polymers.
Highly promising reactions such as enantioselective autocatalysis (Soai reaction) and chiral catalysts undergoing dynamic interconversions, e.g. BIPHEP ligands, are still not understood. Their application is very limited to a few compounds, which opens the field for novel investigations.
I propose the development of a smart or switchable chiral ligand undergoing dynamic interconversions. These catalysts will be tuned by their reaction product, and this leads to self-amplification of one of the stereoisomers. I propose a novel fundamental mechanism which has the potential to overcome the limitations of the Soai reaction, exploiting the full potential of enantioselective catalysis.
As representatives of enantioselective self-amplifying stereodynamic catalysts a novel class of diazirine based ligands will be developed, their interconversion barrier is tuneable between 80 and 130 kJ/mol. Specifically, following areas will be explored:
1. Investigation of the kinetics and thermodynamics of the Soai reaction as a model reaction by analysis of large sets of kinetic data.
2. Ligands with diaziridine moieties with flexible structure will be designed and investigated, to control the enantioselectivity.
3. Design of a ligand receptor group for product interaction to switch the chirality. Study of self-amplification in enantioselective processes.
4. Enantioselective hydrogenations, Diels-Alder reactions, epoxidations and reactions generating multiple stereocenters will be targeted.

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€ 1 452 000,00
69117 Heidelberg

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Baden-Württemberg Karlsruhe Heidelberg, Stadtkreis
Higher or Secondary Education Establishments
Oliver Trapp (Prof.)
Kontakt Verwaltung
Norbert Huber (Dr.)
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Begünstigte (1)