Copper-catalysed conjugate addition to sulfinimines
The synthesis of a series of [alpha],[beta]-unsaturated sulfinimines is described. Their reaction in the presence of copper-based nucleophiles to yield 1,4-addition products is analysed in terms of yield and d.r. values and reported herein. After an introductory chapter, the first section of this th...
| Main Author: | |
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
| Published: |
2016
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| Online Access: | https://eprints.nottingham.ac.uk/37831/ |
| _version_ | 1848795544394137600 |
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| author | Gaunt, Anthony John |
| author_facet | Gaunt, Anthony John |
| author_sort | Gaunt, Anthony John |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | The synthesis of a series of [alpha],[beta]-unsaturated sulfinimines is described. Their reaction in the presence of copper-based nucleophiles to yield 1,4-addition products is analysed in terms of yield and d.r. values and reported herein. After an introductory chapter, the first section of this thesis describes the synthesis and reaction of (R)-(E)-N-((E)-but-2’-en-1’-ylidene)-2-methylpropane-2-sulfinamide in the presence of a series of copper-based nucleophiles – most notably Gilman nucleophiles – displaying yields of up to 54% and 3:2 d.r. values.
The second section of this thesis describes the synthesis of a range of cinnamaldehyde-derived sulfinimines and their reaction in the presence of copper-based nucleophiles – this time derived from alkyl aluminium reagents. Up to quantitative yields and d.r. values of 1:>20 are reported.
In addition, methodology for the synthesis of cinnamaldehyde precursor derivatives via a Meyer-Schuster rearrangement is discussed along with the qualitative identification of competing reactions. |
| first_indexed | 2025-11-14T19:33:46Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-37831 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T19:33:46Z |
| publishDate | 2016 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-378312025-02-28T13:34:35Z https://eprints.nottingham.ac.uk/37831/ Copper-catalysed conjugate addition to sulfinimines Gaunt, Anthony John The synthesis of a series of [alpha],[beta]-unsaturated sulfinimines is described. Their reaction in the presence of copper-based nucleophiles to yield 1,4-addition products is analysed in terms of yield and d.r. values and reported herein. After an introductory chapter, the first section of this thesis describes the synthesis and reaction of (R)-(E)-N-((E)-but-2’-en-1’-ylidene)-2-methylpropane-2-sulfinamide in the presence of a series of copper-based nucleophiles – most notably Gilman nucleophiles – displaying yields of up to 54% and 3:2 d.r. values. The second section of this thesis describes the synthesis of a range of cinnamaldehyde-derived sulfinimines and their reaction in the presence of copper-based nucleophiles – this time derived from alkyl aluminium reagents. Up to quantitative yields and d.r. values of 1:>20 are reported. In addition, methodology for the synthesis of cinnamaldehyde precursor derivatives via a Meyer-Schuster rearrangement is discussed along with the qualitative identification of competing reactions. 2016-12-14 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en arr https://eprints.nottingham.ac.uk/37831/1/Anthony%20Gaunt%20Thesis%202016.pdf Gaunt, Anthony John (2016) Copper-catalysed conjugate addition to sulfinimines. MRes thesis, University of Nottingham. |
| spellingShingle | Gaunt, Anthony John Copper-catalysed conjugate addition to sulfinimines |
| title | Copper-catalysed conjugate addition to sulfinimines |
| title_full | Copper-catalysed conjugate addition to sulfinimines |
| title_fullStr | Copper-catalysed conjugate addition to sulfinimines |
| title_full_unstemmed | Copper-catalysed conjugate addition to sulfinimines |
| title_short | Copper-catalysed conjugate addition to sulfinimines |
| title_sort | copper-catalysed conjugate addition to sulfinimines |
| url | https://eprints.nottingham.ac.uk/37831/ |