Enantioselective synthesis of non-biaryl atropisomers
<p>This thesis describes the development of novel methods to synthesise non-biaryl atropisomers enantioselectively. In Chapter 1, atropisomerism is defined and explored, with a focus on non-biaryl atropisomers and the literature stereoselective syntheses of chiral naphthamides. Chapter 2 discu...
| मुख्य लेखक: | |
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| अन्य लेखक: | |
| स्वरूप: | थीसिस |
| भाषा: | English |
| प्रकाशित: |
2019
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| विषय: |
| _version_ | 1826296195147890688 |
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| author | Fugard, A |
| author2 | Smith, M |
| author_facet | Smith, M Fugard, A |
| author_sort | Fugard, A |
| collection | OXFORD |
| description | <p>This thesis describes the development of novel methods to synthesise non-biaryl atropisomers enantioselectively. In Chapter 1, atropisomerism is defined and explored, with a focus on non-biaryl atropisomers and the literature stereoselective syntheses of chiral naphthamides. Chapter 2 discusses initial attempts to synthesise chiral naphthamides using phase-transfer catalysis, and the barriers to rotation of intermediate enol ethers, and benzylated and debenzylated naphthols are determined. Chapter 3 concerns investigations into the low barriers to rotation of these debenzylated naphthols. Chapter 4 builds on this work to develop an enantioselective synthesis of benzylated naphthamides via a dynamic kinetic resolution of the naphthol starting material. This reaction was tested on a wide variety of substrates to determine its scope and limitations, and the barriers to rotation of the chiral products were calculated.</p> |
| first_indexed | 2024-03-07T04:12:35Z |
| format | Thesis |
| id | oxford-uuid:c8568def-db15-4539-ba7f-2140bcd5698b |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:12:35Z |
| publishDate | 2019 |
| record_format | dspace |
| spelling | oxford-uuid:c8568def-db15-4539-ba7f-2140bcd5698b2022-03-27T06:51:27ZEnantioselective synthesis of non-biaryl atropisomersThesishttp://purl.org/coar/resource_type/c_db06uuid:c8568def-db15-4539-ba7f-2140bcd5698bChemistry, OrganicEnglishORA Deposit2019Fugard, ASmith, M<p>This thesis describes the development of novel methods to synthesise non-biaryl atropisomers enantioselectively. In Chapter 1, atropisomerism is defined and explored, with a focus on non-biaryl atropisomers and the literature stereoselective syntheses of chiral naphthamides. Chapter 2 discusses initial attempts to synthesise chiral naphthamides using phase-transfer catalysis, and the barriers to rotation of intermediate enol ethers, and benzylated and debenzylated naphthols are determined. Chapter 3 concerns investigations into the low barriers to rotation of these debenzylated naphthols. Chapter 4 builds on this work to develop an enantioselective synthesis of benzylated naphthamides via a dynamic kinetic resolution of the naphthol starting material. This reaction was tested on a wide variety of substrates to determine its scope and limitations, and the barriers to rotation of the chiral products were calculated.</p> |
| spellingShingle | Chemistry, Organic Fugard, A Enantioselective synthesis of non-biaryl atropisomers |
| title | Enantioselective synthesis of non-biaryl atropisomers |
| title_full | Enantioselective synthesis of non-biaryl atropisomers |
| title_fullStr | Enantioselective synthesis of non-biaryl atropisomers |
| title_full_unstemmed | Enantioselective synthesis of non-biaryl atropisomers |
| title_short | Enantioselective synthesis of non-biaryl atropisomers |
| title_sort | enantioselective synthesis of non biaryl atropisomers |
| topic | Chemistry, Organic |
| work_keys_str_mv | AT fugarda enantioselectivesynthesisofnonbiarylatropisomers |