Electrodecarboxylative Amination of Malonates Enables the Enantioselective Formation of Non-Natural Amino Acids

• Applicant: Jonas Felix Goebel
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: since 2024
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 542420258

The synthesis of non-natural amino acid derivatives has been a focus of chemical research for over a hundred years. Non-natural amino acids have applications in a variety of fields, including prebiotic experiments such as the Miller-Urey experiment, physiological applications, and post-translational modification of proteins. Modern methods have made significant progress in avoiding toxic substances and reducing the number of steps in desired transformations. Despite these impressive advances, they are still far from ideal. There is still a need for protecting groups and there are limitations in terms of functional group tolerance, especially because most methods are focused on C-C bond linkages and no additional heteroatoms can be introduced, even though they are present in most amino acids used in industry. In contrast, research by the Baran group has already shown that methods such as nickel-catalyzed electrodecarboxylation can act in a stereospecific manner, achieve high yields, and tolerate a wide range of substrates. The extension of this approach to amination reactions offers the potential not only to provide a significantly more efficient method for the synthesis of such compounds, but also to pave the way for numerous similar processes. The planned development of new catalysis and ligand systems can extend the functional group tolerance not only of amination reactions but also of other decarboxylating reactions.

• DFG Programme: WBP Fellowship
• International Connection: USA
• Host: Professor Phil S. Baran, Ph.D.