New applications of rhodium-catalysed hydroacylation
<p>This thesis describes the development of two new rhodium-catalysed hydroacylation methods. The first involves a one-pot hydroacylation/thio-conjugate addition cascade towards the synthesis of fully saturated sulfur heterocycles. The second exploits novel β-sulfonyl aldehydes to access β-ket...
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| Other Authors: | |
| Format: | Thesis |
| Language: | English |
| Published: |
2022
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| Subjects: |
| _version_ | 1797109866353917952 |
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| author | Iwumene, NUN |
| author2 | Willis, M |
| author_facet | Willis, M Iwumene, NUN |
| author_sort | Iwumene, NUN |
| collection | OXFORD |
| description | <p>This thesis describes the development of two new rhodium-catalysed hydroacylation methods. The first involves a one-pot hydroacylation/thio-conjugate addition cascade towards the synthesis of fully saturated sulfur heterocycles. The second exploits novel β-sulfonyl aldehydes to access β-keto-sulfones and sulfonamides.</p>
<p><strong>Chapter 1</strong> delineates a literature review of the evolution of rhodium-catalysed hydroacylation, with focus on catalyst design and chelating groups that hinder decarbonylation. The use of hydroacylation in heterocycle synthesis is also briefly reviewed.</p>
<p><strong>Chapter 2</strong> documents the use of alkynes with pendant sulfur nucleophiles in a highly regioselective rhodium-catalysed hydroacylation reaction, delivering linear α,β-unsaturated enone intermediates. These adducts are further harnessed in intramolecular cyclisation reactions to access diversely substituted, saturated S-heterocycles, in a one-pot fashion.</p>
<p><strong>Chapter 3</strong> outlines initial attempts to develop a rhodium-catalysed hydroacylation methodology for the synthesis of β-keto-sulfones and sulfonamides. The work explores the construction of new β-sulfonyl aldehydes and their use in intermolecular hydroacylation.</p>
<p><strong>Chapter 4</strong> presents the conclusions from the research conducted and future work.</p>
<p><strong>Chapter 5</strong> details the experimental data and procedures.</p> |
| first_indexed | 2024-03-07T07:47:19Z |
| format | Thesis |
| id | oxford-uuid:a899b0d7-10ee-4a26-b5f0-112c874bf343 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T07:47:19Z |
| publishDate | 2022 |
| record_format | dspace |
| spelling | oxford-uuid:a899b0d7-10ee-4a26-b5f0-112c874bf3432023-06-19T10:34:32ZNew applications of rhodium-catalysed hydroacylationThesishttp://purl.org/coar/resource_type/c_db06uuid:a899b0d7-10ee-4a26-b5f0-112c874bf343Organic compounds--SynthesisEnglishHyrax Deposit2022Iwumene, NUNWillis, M<p>This thesis describes the development of two new rhodium-catalysed hydroacylation methods. The first involves a one-pot hydroacylation/thio-conjugate addition cascade towards the synthesis of fully saturated sulfur heterocycles. The second exploits novel β-sulfonyl aldehydes to access β-keto-sulfones and sulfonamides.</p> <p><strong>Chapter 1</strong> delineates a literature review of the evolution of rhodium-catalysed hydroacylation, with focus on catalyst design and chelating groups that hinder decarbonylation. The use of hydroacylation in heterocycle synthesis is also briefly reviewed.</p> <p><strong>Chapter 2</strong> documents the use of alkynes with pendant sulfur nucleophiles in a highly regioselective rhodium-catalysed hydroacylation reaction, delivering linear α,β-unsaturated enone intermediates. These adducts are further harnessed in intramolecular cyclisation reactions to access diversely substituted, saturated S-heterocycles, in a one-pot fashion.</p> <p><strong>Chapter 3</strong> outlines initial attempts to develop a rhodium-catalysed hydroacylation methodology for the synthesis of β-keto-sulfones and sulfonamides. The work explores the construction of new β-sulfonyl aldehydes and their use in intermolecular hydroacylation.</p> <p><strong>Chapter 4</strong> presents the conclusions from the research conducted and future work.</p> <p><strong>Chapter 5</strong> details the experimental data and procedures.</p> |
| spellingShingle | Organic compounds--Synthesis Iwumene, NUN New applications of rhodium-catalysed hydroacylation |
| title | New applications of rhodium-catalysed hydroacylation |
| title_full | New applications of rhodium-catalysed hydroacylation |
| title_fullStr | New applications of rhodium-catalysed hydroacylation |
| title_full_unstemmed | New applications of rhodium-catalysed hydroacylation |
| title_short | New applications of rhodium-catalysed hydroacylation |
| title_sort | new applications of rhodium catalysed hydroacylation |
| topic | Organic compounds--Synthesis |
| work_keys_str_mv | AT iwumenenun newapplicationsofrhodiumcatalysedhydroacylation |