Asymmetric amination reactions with novel chiral ammonium salts

• Applicant: Professor Dr. Stefan Bräse
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2005 to 2009
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 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 Programme: Priority Programmes
• Subproject of: SPP 1179: Organocatalysis