Synthesis of Nitrogen containing Building Blocks with Monothioester Malonates. An Efficient Method for alpha-, beta- and gamma-Amino Acid Derivatives

• Applicant: Sven Peter Fritz, Ph.D.
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2013 to 2014
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 247721463

The importance of thioesters in nature is well established and their chemical potency is exploited by the human body to create the basic building blocks of life, such as peptides, fatty acids and steroids. This proposal aims to use thioester enolates in asymmetric organocatalysis to achieve the synthesis of highly enantioenriched, activated alpha, beta and gamma amino acids. This would be a significant achievement, considering that chiral amino acid derivatives are not only important in protein research, but also the basis of numerous pharmaceuticals and agrochemicals. Each phase of the proposal will develop methods for different chain lengths and configurations of stereocenters, including quaternary stereocenters; then demonstrate the application thereof in the synthesis of known biologically active substrates, such as antibiotics, cholesterol lowering drugs and drugs against diabetes or Parkinson disease. A simultaneously developed screening approach will enable the rapid synthesis and discovery of more efficient catalysts for the developed methodology. The ultimate goal is the creation of a universal tool for the construction of biologically active chains of adjacent stereocenters, closely mimicking natural counterparts, like enzymes.

• DFG Programme: Research Fellowships
• International Connection: Switzerland
• Host: Professorin Dr. Helma Wennemers