Asymmetric synthesis of boronic acids and organofluorine compounds by organocatalysis

This proposal is focused on development of new synthetic methodology for organic synthesis of chiral fluorine and boron containing species.

The practical relevance of the project is based on the broad application of organic fluorine compounds in life-science related areas. About 40% of the block-buster drugs contain at least one C-F bond.

In addition, fluorine-18 labelled compounds are the foremost imaging tracers in Positron Emission Tomography (PET) imaging, which is currently one the most efficient medical diagnostic methods. A novel approach based on asymmetric homologation with organocatalysis will be applied (0-3-years). Some of the precursors of the homologation reaction will be generated by continuous flow synthesis.

The main synthetic targets are potential drug intermediates and tracers for PET (0.5-4-years). The asymmetric homologation will be studied by DFT modelling and experimental mechanistic studies (0.5-4-years).

The DFT modelling studies will be performed in collaboration with colleagues from SU, while the fluorine-18 and carbon-11 labelling studies will be done by my co-workers in collaboration with colleagues from the PET centrums of UU and KI.

The Ph.D. students working on the project will receive a comprehensive training in development of new synthetic methodology, including organocatalysis and continuous flow synthesis, as well as in adaptation of new transformations to labelling of fluorine-18 and carbon-11 of PET tracers.