Synthesis of novel chiral anions and their application in organocatalytic reactions

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The project ChirAnOc is concerned with the molecular understanding and further development of chiral anion mediated organocatalytic processes, in particular on the basis of anion chiral ionic liquids (ILs). Asymmetric counterion directed catalysis (ACDC) has been introduced recently as a powerful alternative in organic synthesis. The use of anion chiral ionic liquids allows to combine their unique solvent properties with an efficient chirality transfer. An exact mechanistic explanation of these reaction systems would help to optimize existing processes and to extend this approach to other catalytic systems. In the present project the research will focus on the development of new chiral borate anion structures. The scope and limitations of these compounds as co-catalysts and solvents will be explored in selected transformations that are mechanistically related to the aza-Baylis-Hillman reaction. Systematic studies will provide a deeper understanding of the chirality transfer in these systems which can contribute to the design of efficient organocatalytic transformations on a broader basis. In the long term, these fundamental studies will enable a knowledge-based design of chiral ions and their application to new reaction systems.