One Pot Silane Mediated Reductive Amination using Methyl Esters as Nominal Electrophiles
Reductive aminations are a commonly employed method of C−N bond formation with a quarter of C−N bond formations in pharmaceutical synthesis performed via a reductive amination. Conventional reductive amination reactions rely on aldehydes as electrophiles which can be difficult to handle as a result...
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
| Published: |
2024
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| Online Access: | https://eprints.nottingham.ac.uk/78012/ |
| _version_ | 1848801045621243904 |
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| author | Cooke, Ishbel |
| author_facet | Cooke, Ishbel |
| author_sort | Cooke, Ishbel |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | Reductive aminations are a commonly employed method of C−N bond formation with a quarter of C−N bond formations in pharmaceutical synthesis performed via a reductive amination. Conventional reductive amination reactions rely on aldehydes as electrophiles which can be difficult to handle as a result of aldol dimerisation and autooxidation. This poster describes a new class of reductive amination reaction in which readily available carboxylic acid esters are used as nominal electrophiles in place of aldehydes. The amination process involves organocatalytic amide formation followed by silane-mediated reduction of the derived amide. The thesis describes the optimisation, scope, and mechanism of this novel amination protocol. |
| first_indexed | 2025-11-14T21:01:13Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-78012 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:01:13Z |
| publishDate | 2024 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-780122024-07-24T04:42:52Z https://eprints.nottingham.ac.uk/78012/ One Pot Silane Mediated Reductive Amination using Methyl Esters as Nominal Electrophiles Cooke, Ishbel Reductive aminations are a commonly employed method of C−N bond formation with a quarter of C−N bond formations in pharmaceutical synthesis performed via a reductive amination. Conventional reductive amination reactions rely on aldehydes as electrophiles which can be difficult to handle as a result of aldol dimerisation and autooxidation. This poster describes a new class of reductive amination reaction in which readily available carboxylic acid esters are used as nominal electrophiles in place of aldehydes. The amination process involves organocatalytic amide formation followed by silane-mediated reduction of the derived amide. The thesis describes the optimisation, scope, and mechanism of this novel amination protocol. 2024-07-24 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en cc_by https://eprints.nottingham.ac.uk/78012/1/thesis%20with%20corrections%20SAVE.pdf Cooke, Ishbel (2024) One Pot Silane Mediated Reductive Amination using Methyl Esters as Nominal Electrophiles. MRes thesis, University of Nottingham. amination carboxylic acid esters electrophiles |
| spellingShingle | amination carboxylic acid esters electrophiles Cooke, Ishbel One Pot Silane Mediated Reductive Amination using Methyl Esters as Nominal Electrophiles |
| title | One Pot Silane Mediated Reductive Amination using Methyl Esters as Nominal Electrophiles |
| title_full | One Pot Silane Mediated Reductive Amination using Methyl Esters as Nominal Electrophiles |
| title_fullStr | One Pot Silane Mediated Reductive Amination using Methyl Esters as Nominal Electrophiles |
| title_full_unstemmed | One Pot Silane Mediated Reductive Amination using Methyl Esters as Nominal Electrophiles |
| title_short | One Pot Silane Mediated Reductive Amination using Methyl Esters as Nominal Electrophiles |
| title_sort | one pot silane mediated reductive amination using methyl esters as nominal electrophiles |
| topic | amination carboxylic acid esters electrophiles |
| url | https://eprints.nottingham.ac.uk/78012/ |