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Title: Selective immobilisation of chiral intermediates in asymmetric synthesis
Author: Dignan, R. A.
Awarding Body: University of Wales Swansea
Current Institution: Swansea University
Date of Award: 2003
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This thesis describes an approach at utilising the ease of purification associated with solid-phase synthesis without encountering the problems associated with two-phase reaction systems. This was achieved by immobilising a bipyridyl-tagged, chiral imidazolidinone auxiliary and chiral oxazaborolidine catalyst by interaction with a solid support upon completion of the solution phase reaction. Chapter one is a literature review of the different approaches to combining the benefits of solid phase synthesis with the benefits of carrying out reactions in single-phase solutions that have been reported. Chapter two is an introduction into chiral auxiliary mediated alkylations, aldol reactions and conjugate additions. Chapter three details the synthesis of a bipyridyl-tagged chiral auxiliary and the results of the investigation into its selective immobilisation. Chapter four describes the investigation into the reactivity of the tagged chiral auxiliary in alkylation, halogenation and aldol reactions. Chapter five describes the selective immobilisation of a bipyridyl-tagged, chiral oxazaborolidine catalyst and details an investigation into the reduction of acetophenone using the tagged catalyst.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available