Utility and Unique Chemistry of Homoallylic Amines with a Difluoromethyl- and Fluoro- Substituted Stereogenic Carbon

Información del proyecto

TRIFLUORO-BUNDLE

Identificador del acuerdo de subvención: 101110967

DOI

10.3030/101110967

Proyecto cerrado

Fecha de la firma de la CE 5 Mayo 2023

Fecha de inicio 1 Septiembre 2023

Fecha de finalización 31 Agosto 2025

Financiado con arreglo a

• Marie Skłodowska-Curie Actions (MSCA)

Coste total

Sin datos

Aportación de la UE

€ 211 754,88

Coordinado por

UNIVERSITE DE STRASBOURG
France

Objetivo

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.

Ámbito científico (EuroSciVoc)

• ciencias naturales › ciencias biológicas › bioquímica › biomoléculas › proteínas
• ciencias naturales › ciencias químicas › química inorgánica › halógenos
• ciencias naturales › ciencias químicas › química orgánica › aminas

Palabras clave

• Organofluorine Compounds
• Homoallylic Amines
• Diastereo- and Enantioselective synthesis
• Difluoromethyl- and Fluoro- Substituted Stereogenic Carbon
• Polyfluoro α-amino acids
• Polyfluoro aza-sugars

Programa(s)

• HORIZON.1.2 - Marie Skłodowska-Curie Actions (MSCA) PROGRAMA PRINCIPAL
  

Tema(s)

• HORIZON-MSCA-2022-PF-01-01 - MSCA Postdoctoral Fellowships 2022
  

Régimen de financiación

HORIZON-TMA-MSCA-PF-EF - HORIZON TMA MSCA Postdoctoral Fellowships - European Fellowships

Convocatoria de propuestas

HORIZON-MSCA-2022-PF-01

Coordinador

UNIVERSITE DE STRASBOURG

• Aportación neta de la UEn: € 211 754,88
• Dirección: RUE BLAISE PASCAL 4 ; 67081 STRASBOURG ; Francia
• Tipo de actividad: Higher or Secondary Education Establishments
• Coste total: Sin datos