Development and understanding of catalytic functionalization of amides and other organic molecules
<p>This thesis describes the development and mechanistic studies of an iridium-catalyzed reductive functionalization of amides and other catalytic transformations. The aim is to reveal and address the details of a wide variety of organic reactions, including some transition metal-catalyzed and...
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| Format: | Thesis |
| Language: | English |
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2022
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| _version_ | 1817933122492170240 |
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| author | Yamazaki, K |
| author2 | Dixon, DJ |
| author_facet | Dixon, DJ Yamazaki, K |
| author_sort | Yamazaki, K |
| collection | OXFORD |
| description | <p>This thesis describes the development and mechanistic studies of an iridium-catalyzed reductive functionalization of amides and other catalytic transformations. The aim is to reveal and address the details of a wide variety of organic reactions, including some transition metal-catalyzed and organocatalytic transformations.</p>
<p>Chapter 1 introduces organic synthesis and computational chemistry and their historical backgrounds. In particular, reactions involving amines and organocatalysis are described. Chapter 2 details the development of the iridium-catalyzed reductive synthesis of azomethine ylides for [3+2] cycloaddition reactions. The unique selectivity of the cyclization reaction was extensively interrogated and explained by means of density functional theory. Chapter 3 describes mechanistic insight into the iridium-catalyzed reductive functionalization of amides. The detailed kinetic and computational studies revealed a full picture of the catalytic cycle and the high chemoselectivity in keeping with all experimental data. Chapter 4 describes computational mechanistic studies of enantioselective catalytic desymmetrization reactions of variously 4-substituted cyclohexanones. Three distinct catalytic reactions are studied, and the origin of the enantio- and diastereoselectivities for the transformations have been uncovered using density functional theory calculations. Chapter 5 describes computational mechanistic studies of enantioselective bifunctional iminophosphorane (BIMP)-catalyzed reactions. Three transformations using the BIMP catalyst are studied, and the chiral induction mechanisms originating from the stabilizing interactions are explained in detail.</p> |
| first_indexed | 2024-03-07T07:43:46Z |
| format | Thesis |
| id | oxford-uuid:4fcc9ea1-fa4c-47a4-ac61-339cc37b15a0 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-12-09T03:48:47Z |
| publishDate | 2022 |
| record_format | dspace |
| spelling | oxford-uuid:4fcc9ea1-fa4c-47a4-ac61-339cc37b15a02024-12-08T11:55:21ZDevelopment and understanding of catalytic functionalization of amides and other organic moleculesThesishttp://purl.org/coar/resource_type/c_db06uuid:4fcc9ea1-fa4c-47a4-ac61-339cc37b15a0Organometallic chemistryComputational chemistryChemistry, OrganicEnglishHyrax Deposit2022Yamazaki, KDixon, DJ<p>This thesis describes the development and mechanistic studies of an iridium-catalyzed reductive functionalization of amides and other catalytic transformations. The aim is to reveal and address the details of a wide variety of organic reactions, including some transition metal-catalyzed and organocatalytic transformations.</p> <p>Chapter 1 introduces organic synthesis and computational chemistry and their historical backgrounds. In particular, reactions involving amines and organocatalysis are described. Chapter 2 details the development of the iridium-catalyzed reductive synthesis of azomethine ylides for [3+2] cycloaddition reactions. The unique selectivity of the cyclization reaction was extensively interrogated and explained by means of density functional theory. Chapter 3 describes mechanistic insight into the iridium-catalyzed reductive functionalization of amides. The detailed kinetic and computational studies revealed a full picture of the catalytic cycle and the high chemoselectivity in keeping with all experimental data. Chapter 4 describes computational mechanistic studies of enantioselective catalytic desymmetrization reactions of variously 4-substituted cyclohexanones. Three distinct catalytic reactions are studied, and the origin of the enantio- and diastereoselectivities for the transformations have been uncovered using density functional theory calculations. Chapter 5 describes computational mechanistic studies of enantioselective bifunctional iminophosphorane (BIMP)-catalyzed reactions. Three transformations using the BIMP catalyst are studied, and the chiral induction mechanisms originating from the stabilizing interactions are explained in detail.</p> |
| spellingShingle | Organometallic chemistry Computational chemistry Chemistry, Organic Yamazaki, K Development and understanding of catalytic functionalization of amides and other organic molecules |
| title | Development and understanding of catalytic functionalization of amides and other organic molecules |
| title_full | Development and understanding of catalytic functionalization of amides and other organic molecules |
| title_fullStr | Development and understanding of catalytic functionalization of amides and other organic molecules |
| title_full_unstemmed | Development and understanding of catalytic functionalization of amides and other organic molecules |
| title_short | Development and understanding of catalytic functionalization of amides and other organic molecules |
| title_sort | development and understanding of catalytic functionalization of amides and other organic molecules |
| topic | Organometallic chemistry Computational chemistry Chemistry, Organic |
| work_keys_str_mv | AT yamazakik developmentandunderstandingofcatalyticfunctionalizationofamidesandotherorganicmolecules |