Investigations into N-Sulfinyl Imino Esters as Versatile Reagents for the Synthesis of N-Sulfinyl Compounds and Unnatural α-Amino Acid Derivatives
N-Sulfinylimino esters are a highly versatile class of compounds, they are already widely used within the pharmaceutical industry for the preparation of chiral α-amines. This work further explores their use as versatile reagents for the synthesis of unnatural α-amino acid derivatives and novel cyc...
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
| Published: |
2023
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| Online Access: | https://eprints.nottingham.ac.uk/76823/ |
| _version_ | 1848800941830045696 |
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| author | Goodrich, Oliver H. |
| author_facet | Goodrich, Oliver H. |
| author_sort | Goodrich, Oliver H. |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | N-Sulfinylimino esters are a highly versatile class of compounds, they are already widely used within the pharmaceutical industry for the preparation of chiral α-amines. This work further explores their use as versatile reagents for the synthesis of unnatural α-amino acid derivatives and novel cyclic sulfinamides.
We investigated and expanded on the stereoselective synthesis of N-sulfinyl amines using an additive free radical 1,3-migration of N-sulfinylimino esters. This allowed the preparation of several tertiary alkyl α-amino esters via the hydrolysis of an N-sulfinyl amine intermediate.
Investigations into this migration led to the development of a novel method for the gram-scale production of tert-leucine ethyl ester in one-step from an N-sulfinyl imino ester using mild conditions and an inexpensive Lewis acid catalyst.
Building on previous literature we prepared 4 novel bicyclic sulfinamides in moderate yields using a Lewis acid mediated [3+2] cycloaddition between cycloalkenes and tert-butyl N-sulfinyl imino esters. |
| first_indexed | 2025-11-14T20:59:34Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-76823 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T20:59:34Z |
| publishDate | 2023 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-768232025-02-28T15:19:31Z https://eprints.nottingham.ac.uk/76823/ Investigations into N-Sulfinyl Imino Esters as Versatile Reagents for the Synthesis of N-Sulfinyl Compounds and Unnatural α-Amino Acid Derivatives Goodrich, Oliver H. N-Sulfinylimino esters are a highly versatile class of compounds, they are already widely used within the pharmaceutical industry for the preparation of chiral α-amines. This work further explores their use as versatile reagents for the synthesis of unnatural α-amino acid derivatives and novel cyclic sulfinamides. We investigated and expanded on the stereoselective synthesis of N-sulfinyl amines using an additive free radical 1,3-migration of N-sulfinylimino esters. This allowed the preparation of several tertiary alkyl α-amino esters via the hydrolysis of an N-sulfinyl amine intermediate. Investigations into this migration led to the development of a novel method for the gram-scale production of tert-leucine ethyl ester in one-step from an N-sulfinyl imino ester using mild conditions and an inexpensive Lewis acid catalyst. Building on previous literature we prepared 4 novel bicyclic sulfinamides in moderate yields using a Lewis acid mediated [3+2] cycloaddition between cycloalkenes and tert-butyl N-sulfinyl imino esters. 2023-12-12 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en cc_by https://eprints.nottingham.ac.uk/76823/1/Thesis%20FINAL.pdf Goodrich, Oliver H. (2023) Investigations into N-Sulfinyl Imino Esters as Versatile Reagents for the Synthesis of N-Sulfinyl Compounds and Unnatural α-Amino Acid Derivatives. PhD thesis, University of Nottingham. Sulfinimines Unnatural Amino Acids Sulfinamides |
| spellingShingle | Sulfinimines Unnatural Amino Acids Sulfinamides Goodrich, Oliver H. Investigations into N-Sulfinyl Imino Esters as Versatile Reagents for the Synthesis of N-Sulfinyl Compounds and Unnatural α-Amino Acid Derivatives |
| title | Investigations into N-Sulfinyl Imino Esters as Versatile
Reagents for the Synthesis of N-Sulfinyl Compounds and
Unnatural α-Amino Acid Derivatives |
| title_full | Investigations into N-Sulfinyl Imino Esters as Versatile
Reagents for the Synthesis of N-Sulfinyl Compounds and
Unnatural α-Amino Acid Derivatives |
| title_fullStr | Investigations into N-Sulfinyl Imino Esters as Versatile
Reagents for the Synthesis of N-Sulfinyl Compounds and
Unnatural α-Amino Acid Derivatives |
| title_full_unstemmed | Investigations into N-Sulfinyl Imino Esters as Versatile
Reagents for the Synthesis of N-Sulfinyl Compounds and
Unnatural α-Amino Acid Derivatives |
| title_short | Investigations into N-Sulfinyl Imino Esters as Versatile
Reagents for the Synthesis of N-Sulfinyl Compounds and
Unnatural α-Amino Acid Derivatives |
| title_sort | investigations into n-sulfinyl imino esters as versatile
reagents for the synthesis of n-sulfinyl compounds and
unnatural α-amino acid derivatives |
| topic | Sulfinimines Unnatural Amino Acids Sulfinamides |
| url | https://eprints.nottingham.ac.uk/76823/ |