Studies towards the asymmetric synthesis of mechanically planar chiral rotaxanes

Abstract

The work reported in this thesis consists of studies towards the asymmetric synthesis of mechanically planar chiral rotaxanes via an asymmetric active template approach. It describes the synthesis of a novel C1-symmetric bis(oxazoline) macrocycle and the investigation of this C1-symmetric bis(oxazoline) macrocycle, and other C1- and C2- symmetric non-macrocyclic bis(oxazoline)s, as ligands in the Cadiot-Chodkiewicz, oxidative Heck and CuAAC ‘click’ reactions as part of the study towards the synthesis of asymmetric planar chiral rotaxanes. 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 C1-symmetric bis(oxazoline) macrocycle. Chapter three describes the investigation of bis(oxazoline)s, C1- and C2-symmetric, macrocyclic and non-macrocyclic, as ligands in the Cadiot-Chodkiewicz, oxidative Heck and CuAAC ‘click’ reaction. Chapter four provides a formal report of the experimental procedures.