N-Heterocyclic Carbenes as Asymmetric Organocatalysts: Reaction Development

Synthetic chemistry is used for the preparation of structurally complex materials on a molecular scale. Complexity in molecules is often associated with chirality - the fundamental property of a structure that renders it non-superimposable on its mirror image. For example, your right hand is chiral because it cannot be superimposed upon its mirror image (your left hand); the right hand is called the enantiomer of the left hand. Chirality also has important consequences, as it means that a right-handed glove cannot be worn on the left hand. This concept of chirality extends to the molecular level, where molecules can exist in two forms that differ only in that the arrangement of their atoms make them mirror images; indeed the majority of biochemical processes involve the interaction of chiral molecules that can exist in non-superimposable mirror image (enantiomeric) forms. This proposal investigates the application of a simple class of chiral organic molecule, known as N-heterocyclic carbenes, for their ability to catalyse selectively the formation of a single enantiomer of a given substance. A modular approach to the design and preparation of these reactive molecules that contain the necessary function and structure to promote catalysis will be used to succeed in this area. The effect of changing the structure of the N-heterocyclic carbene upon its reactivity will also be probed, and the application of these results to asymmetric synthesis and new chemical transformations investigated.