Current Research

Our research is focused on the development of novel synthetic methodology using asymmetric catalysts. Using these we aim for the synthesis of highly functionalized, chiral building blocks, as well as the preparation and investigation of new materials based on fully conjugated π-systems. In addition, we are interested in medicinal chemistry, in particular in the area of neurodegenerative diseases such as morbus Alzheimer.

1) Heterofunctionalization of Unsaturated Hydrocarbons

Cationic gold complexes have been established for the activation of alkenes and alkynes towards the attack of nucleophiles. Therefore, they are used as catalysts for such transformations. 1,4-Diynes incorporating an internal nucleophile undergo a desymmetrization reaction by forming a chiral, heterocyclic compound. Herein, the specific substituent pattern determines regioselectivity:

In the presence of optically active counter-anions and under suitable reaction conditions heterocycles such as pyrrolidines are formed in high enantioselectivity. They can be further functionalized in a chemoselective fashion. Currently, we investigate an application of this new methodology with respect to the total synthesis of alkaloid natural products.

2) Stereoselective Halogenations and Fluoroalkylations

The synthesis of chiral halogenated compounds is of great interest due to their synthetic versatility. However, in contrast to the corresponding O- and N-functionalizations, a much smaller number of reliable methods for their preparations have been established. In particular, we are interested in the halogenation of simple alkenes and Michael acceptors. We have developed a stereoselective fluoroalkylation of crotonic acid derivatives allowing a novel access to highly functionalized synthetic building blocks such as fluorinated butanolides, amino acids, or carbohydrates.

3) Derivatives of Natural Products for Potential Treatment of Neurodegenerative Diseases

Green tea is well established since a long time in traditional Chinese medicine. A compound isolated from these leaves - epi-gallocatechine gallate (EGCG) - was identified recently as a promising new candidate for the prevention or treatment of neurodegenerative diseases such as morbus Alzheimer. The importance of such disorders is continuously increasing giving the demographic trends in industrialized countries. In order to contribute to a better understanding of the specific interactions of EGCG in neuronal cells and potentially pave way to a clinical treatment of Alzheimer´s disease we synthesize EGCG derivatives as drug candidates and investigate their efficacy in collaboration with other pharmacologically and medicinally focused research groups.

4) Fully Conjugated π-Systems as Potential Novel Spintronics Materials

Polyacetylenes were among the first organic polymers in which electrical conductivity was observed. By olefin metathesis polymerization 1,6-heptadiynes can be transformed into such materials with defined side-group and end-group functionalization. In particular, we are interested in polymers with adjustable luminescent, electrochemical, or magnetic properties. Such materials are very interesting for potential spintronics application.

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