Enantio- and Regioselective CH-Functionalization of Cycloalkanes

• Applicant: Dr. Michal Sascha Andrä
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2015 to 2016
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 275392205

During the last decade metal-catalyzed CH-activation with subsequent substitution has emerged as a powerful method to forge new CC-bonds, obviating the need for prefunctionalization of starting materials and enabling rapid diversification of advanced intermediates or natural products. Traditionally, synthetic chemistry relies on functional group interconversions. CH-activation on the other hand offers synthetic routes to target molecules previously impossible and often complementary to the traditional techniques. It holds the potential to dramatically shorten synthetic sequences, thus minimizing chemical waste, reducing prices of fine chemicals and enabling a more efficient development and even production of pharmaceutically active compounds. At the moment, CH-activation is maturing from the academic curiosity it was in the 1970s into a stan-dard method in the toolbox of synthetic chemistry. However, particularly C(sp³)H-activation still suffers from poor selectivity due to the vast number of CH bonds present in organic molecules: To this date, a regioselective, directed functionalization of C(sp³)H-bonds has not been realized. In this project, I will develop a method for CH-activation of a model-system with unprecedented high level of control in CH-activation, building on previous experimental results. After the necessary first steps, the method will be applied to rapidly synthesize a small substance library from a natural product with interesting pharmacological activities, thus demonstrating its potential in total synthesis, medicinal chemistry and pharmaceutical industry.

• DFG Programme: Research Fellowships
• International Connection: USA
• Host: Professor Jin-Quan Yu, Ph.D.