Enantioselective transformations and continuous-flow synthesis of fluorinated diazoalkanes

• Applicant: Professor Dr. Rene M. Koenigs
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2018 to 2021
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 408033718

Fluorinated diazo alkanes are a long established class of compounds, yet the synthetic applicability of these small and highly reactive molecules has only recently been investigated. Enantioselective transformations of these reagents and their synthesis in continuous-flow have so far been hardly addressed and allow novel applications for the synthesis of fluorinated molecues.The aim of this research project is to investigate these fluorinated diazoalkanes in enantioselective rearrangement reactions. This type of reaction is still one of the major challenges in asymmetric catalysis and has hardly been studied so far. Rearrangement reactions with fluorinated diazoalkanes provide novel access to valuable fluorinated, highly functionalized heterocycles and building blocks.In a second part, non-isolable fluorinated diazoalkanes will be investigated in continuous-flow. This way, these highly reactive diazo compounds can be safely made available for organic synthesis. Thus, new and unique transformations for organic synthesis can be investigated. This concept opens up efficient access to chemical space, which until now has been difficult to address synthetically.

• DFG Programme: Research Grants