Asymmetric amination reactions with novel chiral ammonium salts

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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.