2,3,4-Trisubstituted piperidines. A stereocontolled approach

摘要

This thesis details a methodology utilising various synthetic pathways towards cyclisation precursors suitable for use in Prins and carbonyl-ene cyclisations to effect 2,3,4-trisubstituted piperidines. Once the precursors were synthesised, we were interested in the stereochemical outcomes of the cyclisations, in particular identity and rational of the kinetic and thermodynamic products and their variation due to differing substituents on C2. Previous work in the Snaith group has addressed various other substitution patterns and 2,3,4-trisubstituted piperidines are central components of a vast array of drug targets and natural products, so it follows that these should also be sought via similar processes. Synthesis of the precursors proved to be much more challenging than anticipated, hence many different routes were investigated with fluctuating successes.