The contents of this Thesis herein describe the catalytic asymmetric epoxidation of simple unfunctionalised alkenes. The first chapter, the introduction, describes some of the most successful procedures to date with respect to the asymmetric epoxidation of simple unfunctionalised alkenes. The second chapter, the results and discussion, describes previous work in the Page group in the area of asymmetric epoxidations and progresses to describe the current author's research in this area. This is focussed on the synthesis of several novel carbohydrate based dihydroisoquinolinium salt systems and their subsequent screening with respect to the asymmetric epoxidation of E-methylstilbene, triphenylethylene and 1-phenylcyclohexene. Most of the catalysts synthesised in this study were tested under both the aqueous and non-aqueous conditions developed within the Page group, where it was found that the non-aqueous conditions offered better catalytic activity for this family of catalysts. The best catalytic activities and enantioselectivities in the asymmetric epoxidation of the test substrates were obtained with some of the galactose-derived dihydroisoquinolinium salt systems. At best, enantioselectivities as high as 59% were obtained. Chapter three contains full experimental details for the synthetic studies carried out in chapter two. Finally, the appendix contains X-ray crystallographic data of two compounds synthesised in this study.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:428786 |
| Date | January 2006 |
| Creators | Doswell, Lavril |
| Publisher | Loughborough University |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | https://dspace.lboro.ac.uk/2134/35567 |
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