Asymmetric amination reactions with novel chiral ammonium salts

通过不对称碳氮键的形成来合成对映体纯胺衍生物是其制备的最直接的方法之一。基于我们新开发的氯胺-t高效醛酮胺化反应，我们开发了一种手性相转移催化剂的不对称有机催化，具有很好的对映体选择能力。虽然起始材料很容易获得，但氯胺- t是一种环境友好的试剂，只产生氯化钠作为副产物。由于胺化产物可以在蛋白源性和非蛋白源性-氨基酸中两步转化，因此可以直接获得这些产物。新型手性相转移催化剂的合成与应用以及整个工艺流程的优化是本研究的重要组成部分。用现代核谱学和ESI质谱法对其独特的反应机理进行了阐述。

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.