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Title: Studies towards solid-phase nitrone cycloaddition reactions
Author: Henderson, A. J.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 1999
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The work outlined in this thesis is directed towards the use of resin-bound nitrones in 1,3-dipolar cycloaddition reactions towards the synthesis of heterocyclic compounds. Chapter one provides a brief introduction of a solid-phase synthesis, highlighting some key elements within the technique. A detailed review of solid-phase 1,3-dipolar cycloaddition reactions follows this. Chapter two describes the solution-phase model studies carried out towards an intramolecular 1,3-dipolar cycloaddition on a solid support. Interesting developments such as the effect of the nitrone substituent R on the cycloaddition of 2.121 and various enolate alkylation methods are reported. Furthermore, studies towards novel linker methodologies based on sulfur linked substrates such as 2.57 are outlined. Fig. 11,050A. In Chapter 3, the conventional intramolecular 1,3-dipolar cycloaddition methodology is translated to the solid-phase with limited success. Preparation of the isoxazolidine 3.8 is reported, with subsequent cleavage. Additionally, the problems encountered with alkylation reactions and resin stability are extensively discussed. Fig. 11,050B. Chapter 4 introduces intramolecular nitrone-olefin 1,3-dipolar cycloaddition reactions in solution and solid-phase. The conventionally synthesised adduct 4.21 is compared with the solid-phase synthesised analogue 4.40 with some interesting differences in the stereochemical outcome of both.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available