Synthesis of nitrogen containing heterocycles

Thesis

This thesis is concerned with the development of synthetic methodology for the synthesis of nitrogen containing heterocycles, specifically 2,5-disubstituted pyrrolidines, 2,6-disubstituted piperidines and 3,5-disubstituted indolizidines.

Chapter 1 introduces current methods for the formation of 3,5-disubstituted indolizidines.

Chapter 2 describes studies into the asymmetric synthesis of both cis- and trans-2,5-disubstituted pyrrolidines via a diastereodivergent intramolecular aza-Michael reaction.

Chapter 3 describes attempts to apply the diastereodivergent intramolecular aza-Michael methodology, developed in chapter two, to the synthesis of cis- and trans-2,6-disubstituted piperidines. Investigations into extending the scope of the Davies' lithium amide conjugate addition methodology to the synthesis of polysubstituted piperidines is also described.

Chapter 4 describes the conversion of the cis- and trans-2,5-disubstituted pyrrolidines, synthesised in chapter two, into an indolizidine core. One of the diasteroisomers is subsequently elaborated into the natural product monomorine.

Chapter 5 contains full experimental procedures and characterisation data for all compounds synthesised in Chapters 2, 3, 4.

Authors: White, A

• DOI: 10.5287/ora-orzdxkvv1
• Type of award: MSc by Research
• Level of award: Masters
• Awarding institution: University of Oxford