Degree Name

Master of Science by Research


Department of Chemistry - Faculty of Science


This thesis describes the results of two independent research projects. The first project is concerned with the synthesis of chiral 1,2-amino alcohols using an organocatalysed Mannich reaction. Chapter 1 gives an overview of L-proline catalysed Mannich reactions and describes the aims of this project. Chapter 2 reports the results of this study. These reactions were found to be low yielding and poorly diastereoselective with the model compound propanal and did not work with the desired aldehyde O-benzylglycosaldehyde. The stereochemical outcomes of these reactions using NMR analysis were not certain. Future work would require X-ray crystallographic studies to confirm the product relative stereochemistries. This project was thus abandoned and a second project was studied. Chapter 3 provides an overview of cyclic N-acyliminium ion chemistry. Chapter 4 describes the results of a study of the borono-Mannich reaction on N-acyliminium ions, generated in situ from hemi-aminals derived from chiral 5-hydroxypyrrolidin-2-ones, to prepare substituted pyrrolidinones. The reactions of these N-acyliminium ions with boronic acids and other nucleophiles can afford the corresponding substituted pyrrolidinones diastereoselectively. The stereochemical assignments of these products were based on NMR coupling constants. X-ray structures of these compounds would be required in the future to confirm these assignments. The success of these reactions provided a possible strategy for the synthesis of functionalized pyrrolidinones and other potential glycosidases inhibitors.

02Whole.pdf (1068 kB)



Unless otherwise indicated, the views expressed in this thesis are those of the author and do not necessarily represent the views of the University of Wollongong.