Rhodium catalysed hydroacylation reactions in the synthesis of heterocycles
<p>Rhodium-catalysed hydroacylation provides a highly atom economic synthesis of ketone products from the combination of aldehydes and multiple bond systems by C-H bond activation. This work evaluates the combination of intermolecular hydroacylation for the synthesis of classical heterocycle p...
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| Format: | Thesis |
| Language: | English |
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2011
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| _version_ | 1826315587019603968 |
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| author | Ylioja, P |
| author2 | Willis, M |
| author_facet | Willis, M Ylioja, P |
| author_sort | Ylioja, P |
| collection | OXFORD |
| description | <p>Rhodium-catalysed hydroacylation provides a highly atom economic synthesis of ketone products from the combination of aldehydes and multiple bond systems by C-H bond activation. This work evaluates the combination of intermolecular hydroacylation for the synthesis of classical heterocycle precursors and their dehydrative cyclisation to give rise to a range of substituted heterocyclic compounds.</p><p>Chapter 1 outlines recent developments in the chemistry of hydroacylation. Particular attention is paid to the various chelation strategies employed in intermolecular hydroacylation. Chapter 2 discusses some relevant and recent developments in the field of pyridine and pyrrole synthesis.</p><p>Having established that β-sulphur chelation controlled hydroacylation can be used to synthesise pyridines in Chapter 3; attention was turned to hydroacylation of propargyl amines in Chapter 4. The methodology was expanded to provide a synthesis of γ-amino enones. The hydroacylation reaction and cyclisation is combined in a procedure that utilises thermal Boc-deprotection and cyclisation to give a range of highly-substituted pyrroles.</p><p>The regioselectivity of the hydroacylation of propargyl amines is investigated in Chapter 5 by application of statistical Design of Experiments methodology. Optimised conditions were identified with minor improvements in the selectivity of the reaction.</p> |
| first_indexed | 2024-03-06T18:37:40Z |
| format | Thesis |
| id | oxford-uuid:0bd31ddc-c13e-4502-b359-64495a297489 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-12-09T03:28:57Z |
| publishDate | 2011 |
| record_format | dspace |
| spelling | oxford-uuid:0bd31ddc-c13e-4502-b359-64495a2974892024-12-01T11:42:38ZRhodium catalysed hydroacylation reactions in the synthesis of heterocyclesThesishttp://purl.org/coar/resource_type/c_db06uuid:0bd31ddc-c13e-4502-b359-64495a297489Organic synthesisSynthetic organic chemistryCatalysisOrganic chemistryHeterocyclic chemistryOrganometallic ChemistryEnglishOxford University Research Archive - Valet2011Ylioja, PWillis, MHowsham, C<p>Rhodium-catalysed hydroacylation provides a highly atom economic synthesis of ketone products from the combination of aldehydes and multiple bond systems by C-H bond activation. This work evaluates the combination of intermolecular hydroacylation for the synthesis of classical heterocycle precursors and their dehydrative cyclisation to give rise to a range of substituted heterocyclic compounds.</p><p>Chapter 1 outlines recent developments in the chemistry of hydroacylation. Particular attention is paid to the various chelation strategies employed in intermolecular hydroacylation. Chapter 2 discusses some relevant and recent developments in the field of pyridine and pyrrole synthesis.</p><p>Having established that β-sulphur chelation controlled hydroacylation can be used to synthesise pyridines in Chapter 3; attention was turned to hydroacylation of propargyl amines in Chapter 4. The methodology was expanded to provide a synthesis of γ-amino enones. The hydroacylation reaction and cyclisation is combined in a procedure that utilises thermal Boc-deprotection and cyclisation to give a range of highly-substituted pyrroles.</p><p>The regioselectivity of the hydroacylation of propargyl amines is investigated in Chapter 5 by application of statistical Design of Experiments methodology. Optimised conditions were identified with minor improvements in the selectivity of the reaction.</p> |
| spellingShingle | Organic synthesis Synthetic organic chemistry Catalysis Organic chemistry Heterocyclic chemistry Organometallic Chemistry Ylioja, P Rhodium catalysed hydroacylation reactions in the synthesis of heterocycles |
| title | Rhodium catalysed hydroacylation reactions in the synthesis of heterocycles |
| title_full | Rhodium catalysed hydroacylation reactions in the synthesis of heterocycles |
| title_fullStr | Rhodium catalysed hydroacylation reactions in the synthesis of heterocycles |
| title_full_unstemmed | Rhodium catalysed hydroacylation reactions in the synthesis of heterocycles |
| title_short | Rhodium catalysed hydroacylation reactions in the synthesis of heterocycles |
| title_sort | rhodium catalysed hydroacylation reactions in the synthesis of heterocycles |
| topic | Organic synthesis Synthetic organic chemistry Catalysis Organic chemistry Heterocyclic chemistry Organometallic Chemistry |
| work_keys_str_mv | AT yliojap rhodiumcatalysedhydroacylationreactionsinthesynthesisofheterocycles |