Chiral mono- and bifunctional organic catalysts: A joint experimental-theoretical approach to asymmetric organic synthesis

• Antragstellerinnen / Antragsteller: Professor Dr. Timothy Clark; Professorin Dr. Svetlana Tsogoeva
• Fachliche Zuordnung: Organische Molekülchemie - Synthese, Charakterisierung
• Förderung: Förderung von 2005 bis 2012
• Projektkennung: Deutsche Forschungsgemeinschaft (DFG) - Projektnummer 5451529

In this project the scope of the new chiral primary amine-thiourea and guanidine-thiourea catalysts developed in our laboratory will be extended to other useful reactions that can use N-Boc-imines as substrates (e.g. the Strecker synthesis, Mannich and aza-Henry reactions, etc.), and to natural product syntheses via Diels-Alder and hetero-Diels-Alder reactions. Further design and synthesis of new bifunctional frameworks that contain both the Lewis-base unit (e. g. formamides, sulfoxides, etc.) and the thiourea moiety, and that can activate both nucleophiles and electrophiles simultaneously via non-covalent interactions, will be carried out. The development of an asymmetric organocatalytic version of [3+2] cycloaddition reactions that is applicable to the synthesis of pyrazolidines (an interesting class of heterocyclic compounds), and the development of new organocatalytic systems for different organic transformations in the presence of water without using organic solvents is a further goal. This research is characterized by close cooperation and continuous feedback between theoretical investigations that make use of electronic structure calculations and statistical rate theory and experiment.

• DFG-Verfahren: Schwerpunktprogramme
• Teilprojekt zu: SPP 1179: Organokatalyse