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Novel selenium catalysis

By Danielle Michelle Browne

Abstract

This thesis describes work carried out on catalytic selenium reagents in a range of organic transformations. Four different areas have been investigated and are reported herein. Chapter 2 reports the unsuccessful development into prochiral ligands, where three different chalcogen atoms are incorporated into either a trisubstituted structure or into a crown ether ring. Then reports how these structures could attach to a metal atom and become chiral. A SSe I SeR Chapter 3 describes a range of selenium-based ligands, which has been used in the palladium allylic substitution reaction to see if there is good co-ordination between selenium and palladium and if good enantioselectivities can be achieved. Chapter 4 describes the use of seleninic acids as catalysts in a range of reactions where the most successful is used in asymmetric Baeyer-Villiger oxidations using a range of ketones with enantiotopic migrating groups. The enantioselectivities were investigated. Chiral Catalyst I I ,0 O H202 O ASe A X R O R R CH2CI2 R ' Chiral Catalyst Chapter 5 describes the successful work on catalytic selenium reagents used to convert /,y-alkenoic acids into their corresponding butenolides. The work describes the optimum conditions investigated, asymmetric version of the reaction and also investigates mechanistic aspects of the catalytic cycle. Cat - (PhSe)2 Oxidant R 0 R C00H ' _J Solvent

Topics: QD Chemistry
Year: 2008
OAI identifier: oai:http://orca.cf.ac.uk:54706
Provided by: ORCA
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