Objective
Organofluorine compounds are scarce in natural products, but they are central to therapeutic science, agrochemical development and materials research. Incorporation of fluorine atoms within an organic molecule can have profound effects on pharmacokinetic and pharmacodynamic properties. Enantiomerically enriched fluoro amino acids possess physiochemical and biological properties that distinguish them from canonical amino acids and are key to advances in biological sciences, including peptide and protein engineering. On another front, many azasugars that have high pharmacological potential suffer from weak binding affinities and inferior pharmacokinetic properties; this problem may be addressed through glycomimetics. A promising strategy in glycomimetics entails H-to-F and OH-to-CF2H exchange.
A compelling objective in modern chemistry, therefore, is the development of efficient, and practical strategies for diastereo- and enantioselective synthesis of readily modifiable organofluorine fragments that have a CF2H moiety. However, while enantioselective methods that can be used to form a C(sp3)CF2H stereocenter are available, none apply to the formation of products bearing a fully substituted carbon stereogenic center that has a CF2H and a F substituent. To address this problem, we will develop a robust, practical, and scalable catalytic strategy for practical, efficient, diastereo- and enantioselective conversion of nitriles to homoallylic amines with a CF2H- and F-substituted allylic carbon. Our investigations will focus on an important but severely underdeveloped class of transformations, namely, catalytic diastereo- and enanantioselective addition of a carbon-based nucleophile to nitriles. We plan to utilize the new catalytic approach as the key design element in highly efficient diastereo- and enantioselective syntheses of polyfluoro -amino acids, and aza-sugars, bearing a fully substituted carbon stereogenic center that has a CF2H and a F substituent.
Fields of science (EuroSciVoc)
CORDIS classifies projects with EuroSciVoc, a multilingual taxonomy of fields of science, through a semi-automatic process based on NLP techniques.
CORDIS classifies projects with EuroSciVoc, a multilingual taxonomy of fields of science, through a semi-automatic process based on NLP techniques.
- natural sciencesbiological sciencesbiochemistrybiomoleculesproteins
- natural scienceschemical sciencesinorganic chemistryhalogens
- natural scienceschemical sciencesorganic chemistryamines
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Keywords
Programme(s)
- HORIZON.1.2 - Marie Skłodowska-Curie Actions (MSCA) Main Programme
Funding Scheme
HORIZON-TMA-MSCA-PF-EF - HORIZON TMA MSCA Postdoctoral Fellowships - European FellowshipsCoordinator
67081 Strasbourg
France