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Title: Rhodium and iridium-catalysed nucleophilic addition/substitution reactions for the synthesis of lead-like scaffolds
Author: Li, Ho Yin
Awarding Body: University of Leeds
Current Institution: University of Leeds
Date of Award: 2012
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The research project presented in this thesis aimed to synthesise lead-like scaffolds under array conditions utilizing a novel metal catalysed reaction sequence. The reaction sequence was designed to synthesize libraries of compounds with structural diversity and maximum functional group compatibility in order to aid organic synthesis in modern medicinal industry. The first part of this thesis involved the study of rhodium-catalysed conjugate addition of boronic acids/esters to various Michael acceptors. This methodology has been investigated in order to expand the nucleophile scope to ortho-substituted functionalised (hetero)arylboronic acids/esters for the synthesis of benzo-fused heterocycles in good yield and diastereoselectivity. The potential for asymmetric conjugate addition has been explored with limited success. The second part of this thesis involved the study of iridium-catalysed asymmetric allylic substitution of amines to allylic carbonates. The synthesis of chiral polyamine intermediates was achieved in good yield, regio- and stereoselectivity by using diamine nucleophiles. A limited study has been performed to investigate the potential divergent synthesis of small, polar, highly functionalized chiral molecules. It has been demonstrated that by applying both methodologies, libraries of 'structurally diverse compounds can be synthesised from a small number of starting materials.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available