This project is concerned with the design, synthesis and validation of new hairpin-turn mimics, and their exploitation in asymmetric catalysis through the development of cooperatively-enhanced hydrogen-bonding catalysts. The aims of this research are: 1. The design and synthesis of a range of novel nonpeptidic turn mimics. This will involve the delineation of novel design and build principles for this important secondary structural element, and conformational elucidation through a range of spectroscopic techniques. 2. The exploitation of these materials in the generation of novel sheet-like materials. The generation of sheet-forming materials is an important validation step for new hairpin turn structures. 3. The development of a range of hydrogen-bonding catalysts based on these turn structures that adopt well-defined secondary structures and operate via cooperatively enhanced hydrogen bonding. This will involve the decoration of the turn scaffold with appropriate functional groups and elucidation of their conformation. 4. Investigation and exploitation of the catalytic properties of these materials. This will lead to the development of a range of novel catalytic asymmetric transformations. We propose the union of these two fields in the belief that a fundamental understanding of hydrogen bonding, and the ability to manipulate this phenomenon as a tool is essential in the design of catalysts with enzyme-like reactivity and selectivity. As a consequence, this project has the potential to impact significantly on the two fields of foldamer design and asymmetric catalysis.
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