Asymmetric amination reactions with novel chiral ammonium salts

• Antragsteller: Professor Dr. Stefan Bräse
• Fachliche Zuordnung: Organische Molekülchemie - Synthese, Charakterisierung
• Förderung: Förderung von 2005 bis 2009
• Projektkennung: Deutsche Forschungsgemeinschaft (DFG) - Projektnummer 5451726

The synthesis of enantiomerically pure amine derivatives by asymmetric formation of carbonnitrogen bonds is one of the most straightforward methods for their preparation. Based on our newly developed highly efficient -amination reaction of aldehydes and ketones using chloramine-T, we developed an asymmetric organo-catalysis using chiral phase-transfer catalysts with promising enantioselection. While the starting materials are readily available, chloramine-T is an environmentally benign reagent which gives only sodium chloride as a byproduct. Since the aminated products can be converted in two steps in proteogenic and nonproteinogenic -amino-acids, a straightforward access to these products is achievable. The synthesis and application of new chiral phase-transfer catalysts and optimization of this overall process, are important parts of work-packages. The unique reaction mechanism will be elucidated modern nuclear spectroscopy and ESI mass spectroscopy.

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