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Title: Synthesis and applications of polymer-bound chiral epoxidation catalysts
Author: Liu, C. H.
Awarding Body: University of Wales Swansea
Current Institution: Swansea University
Date of Award: 2001
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We have prepared polymer-supported unsymmetrical chiral (salen)Mn complexes (11.2) for asymmetric epoxidations; the link to the polymer was made between a single hydroxypropyl group attached to a Katsuki complex and polystyrenecarboxyl chloride. The polymer is as enantioselective in its catalysis of epoxidation of dihydronaphthalene as the Katsuki complexes, but more easily recovered for reuse. Excellent enantioselectivity (≥94% ee) was achieved and the polymeric catalyst was recycled up to 5 times with minimal loss in enantioselectively. The immobilized chiral (salen)Mn complex was formed by treatment of a polystyrenecarboxyl chloride with an unsymmetrical chiral (salen) complex (8.2), treatment with NaPF6. Unsymmetrical ligand 8.1 was synthesised from (R)-3-formyl-2-hydroxy-6-(3-hydroxypropyl)-2'-phenyl-1,1'-binaphtalene (7.1) and (R)-3-formyl-2-hydroxy-2'-phenyl-1,1'-binaphthalene (7.2) via a 1S,2S-diaminocyclohexane bridge. Chapters 1 and 2 introduce asymmetric epoxidation and functionalized polymers, respectively. They provide reviews of recent work in the field, including work on polymer-supported chiral (salen)Mn complex catalysts. Chapter 3 outlines the nature of the research project. Chapters 4-6 describe the syntheses of racemic salicylaldehyde derivatives that would eventually be incorporated into an unsymmetrical Katsuki complex. Chapter 7 describes the application of the successful routes to homochiral substrates. Chapter 8 discusses the preparation of the unsymmetrical chiral salen ligand (8.1) and (salen)Mn complexes (8.2).
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available