Third generation of reoxidant for osmium: extension and novel applications

Thesis

This thesis describes the development of new osmium-mediated methodologies providing novel applications through the use of a third generation of reoxidant for osmium.

Chapter 1 The introduction

• Summary of past and present methodologies towards the synthesis of the 1,2 amino alcohol motif.

Chapter 2 Intramolecular processes

• The studies of the tethered aminohydroxylation (TA) of amide and urea derivatives are being investigated.

Chapter 3 Investigations towards an intermolecular process

• The transposition of the TA methodology to an intermolecular process and the requirements involved are discussed. The role of acetamide is being investigated.

Chapter 4 Successful transition to an intermolecular process

• Amino acid derivatives became for the first time possible nitrogen sources and were efficiently employed through osmium-mediated reaction to afford interesting biological scaffolds.

Chapter 5 Experimental

• Full experimental procedures and characterisation of compounds are reported.

References

• A complete list of citations employed in the previous five chapters is provided.

Appendix

• Full documentation of X-ray crystal structures, key NMR spectra and HPLC traces is provided.

Authors: Callens, C

• Publication date: 2011
• Type of award: DPhil
• Level of award: Doctoral
• Awarding institution: Oxford University, UK
• Language: English
• Keywords: osmium; intramolecular; aminoacids; amide; tethered aminohydroxylation; intermolecular
• Subjects: Organic chemistry; Organic synthesis