Trading N and O. Part 4: Asymmetric synthesis of syn-β-substituted-α-amino acids
A total of nine enantiopure syn-β-substituted-α-amino acids have been synthesised, comprising both syn-β-hydroxy-α-amino acids and syn-β-fluoro-α-amino acids. The key step in the synthetic strategy towards these syn-β-substituted-α-amino acids involves a stereospecific rearrangement, which proceeds...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
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Elsevier
2018
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| _version_ | 1826301992902852608 |
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| author | Davies, S Fletcher, A Greenaway, C Kennedy, M Mayer, C Roberts, P Thomson, J |
| author_facet | Davies, S Fletcher, A Greenaway, C Kennedy, M Mayer, C Roberts, P Thomson, J |
| author_sort | Davies, S |
| collection | OXFORD |
| description | A total of nine enantiopure syn-β-substituted-α-amino acids have been synthesised, comprising both syn-β-hydroxy-α-amino acids and syn-β-fluoro-α-amino acids. The key step in the synthetic strategy towards these syn-β-substituted-α-amino acids involves a stereospecific rearrangement, which proceeds via the intermediacy of the corresponding aziridinium ions. The requisite enantiopure syn-α-hydroxy-β-amino esters were prepared via asymmetric aminohydroxylation of the corresponding α,β-unsaturated esters followed by epimerisation of the resultant anti-α-hydroxy-β-amino esters at the C(2)-position. Subsequent activation of the α-hydroxy moiety as a leaving group followed by displacement by the β-amino substituent gave the corresponding aziridinium species. Regioselective in situ ring-opening of the aziridinium intermediates with either water or fluoride gave the corresponding syn-β-hydroxy-α-amino ester or syn-β-fluoro-α-amino ester, respectively, and N-deprotection and ester hydrolysis afforded the target syn-β-substituted-α-amino acids as single diastereoisomers in good overall yield. |
| first_indexed | 2024-03-07T05:40:47Z |
| format | Journal article |
| id | oxford-uuid:e57dfc99-eae1-47b9-8788-5278f67af91a |
| institution | University of Oxford |
| last_indexed | 2024-03-07T05:40:47Z |
| publishDate | 2018 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | oxford-uuid:e57dfc99-eae1-47b9-8788-5278f67af91a2022-03-27T10:24:21ZTrading N and O. Part 4: Asymmetric synthesis of syn-β-substituted-α-amino acidsJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:e57dfc99-eae1-47b9-8788-5278f67af91aSymplectic Elements at OxfordElsevier2018Davies, SFletcher, AGreenaway, CKennedy, MMayer, CRoberts, PThomson, JA total of nine enantiopure syn-β-substituted-α-amino acids have been synthesised, comprising both syn-β-hydroxy-α-amino acids and syn-β-fluoro-α-amino acids. The key step in the synthetic strategy towards these syn-β-substituted-α-amino acids involves a stereospecific rearrangement, which proceeds via the intermediacy of the corresponding aziridinium ions. The requisite enantiopure syn-α-hydroxy-β-amino esters were prepared via asymmetric aminohydroxylation of the corresponding α,β-unsaturated esters followed by epimerisation of the resultant anti-α-hydroxy-β-amino esters at the C(2)-position. Subsequent activation of the α-hydroxy moiety as a leaving group followed by displacement by the β-amino substituent gave the corresponding aziridinium species. Regioselective in situ ring-opening of the aziridinium intermediates with either water or fluoride gave the corresponding syn-β-hydroxy-α-amino ester or syn-β-fluoro-α-amino ester, respectively, and N-deprotection and ester hydrolysis afforded the target syn-β-substituted-α-amino acids as single diastereoisomers in good overall yield. |
| spellingShingle | Davies, S Fletcher, A Greenaway, C Kennedy, M Mayer, C Roberts, P Thomson, J Trading N and O. Part 4: Asymmetric synthesis of syn-β-substituted-α-amino acids |
| title | Trading N and O. Part 4: Asymmetric synthesis of syn-β-substituted-α-amino acids |
| title_full | Trading N and O. Part 4: Asymmetric synthesis of syn-β-substituted-α-amino acids |
| title_fullStr | Trading N and O. Part 4: Asymmetric synthesis of syn-β-substituted-α-amino acids |
| title_full_unstemmed | Trading N and O. Part 4: Asymmetric synthesis of syn-β-substituted-α-amino acids |
| title_short | Trading N and O. Part 4: Asymmetric synthesis of syn-β-substituted-α-amino acids |
| title_sort | trading n and o part 4 asymmetric synthesis of syn β substituted α amino acids |
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