Studies towards the asymmetric synthesis of cyclochiral rotaxanes and Au(III)-oxo complexes as catalysts.

The work reported in this thesis consists of studies towards the asymmetric synthesis of mechanically planar chiral rotaxanes via desymmetrisation approach. It describes the synthesis of a novel macrocycle and the investigation of this macrocycle as a potential ligand in the Cadiot-Chodkiewicz and CuAAC ‘click’ reactions as part of the study towards the synthesis of asymmetric planar chiral rotaxanes. Furthermore, the use of Au(III)-oxo complexes as potential catalysts in a model hydroamination reaction are described. The thesis is divided into four chapters: Chapter one is an introduction to rotaxanes and includes an overview of the synthesis of rotaxanes and chirality in rotaxanes. Chapter two is an account of the synthesis of a novel macrocycle and details attempts to implement this macrocycle towards the synthesis of a rotaxane using the Cadiot-Chodkiewicz and CuAAC ‘click’ reactions. Chapter three describes optimisation and multi-gram scale-up of the synthetic route towards a novel C1-symmetric bis(oxazoline) macrocycle first synthesised in our group by Pauline Glen. Chapter four describes our investigation into the use of Au(III)-oxo complexes for use as catalysts in a model hydroamination reaction.Engineering and Physical Sciences Research Council (EPSRC) funding