Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine.
The highly diastereoselective anti-aminohydroxylation of alpha,beta-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine, has been used as the key step in the asymmetric synthesis...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2008
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| _version_ | 1826297670937870336 |
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| author | Abraham, E Davies, S Millican, N Nicholson, R Roberts, P Smith, A |
| author_facet | Abraham, E Davies, S Millican, N Nicholson, R Roberts, P Smith, A |
| author_sort | Abraham, E |
| collection | OXFORD |
| description | The highly diastereoselective anti-aminohydroxylation of alpha,beta-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine, has been used as the key step in the asymmetric synthesis of N,O-diacetyl xestoaminol C (41% yield over 8 steps), N,O,O-triacetyl sphinganine (30% yield over 8 steps) and N,O,O-triacetyl sphingosine (30% yield over 7 steps). |
| first_indexed | 2024-03-07T04:35:13Z |
| format | Journal article |
| id | oxford-uuid:cfb42e87-79aa-4cb6-aef2-f6d8c66c4470 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:35:13Z |
| publishDate | 2008 |
| record_format | dspace |
| spelling | oxford-uuid:cfb42e87-79aa-4cb6-aef2-f6d8c66c44702022-03-27T07:44:30ZAsymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:cfb42e87-79aa-4cb6-aef2-f6d8c66c4470EnglishSymplectic Elements at Oxford2008Abraham, EDavies, SMillican, NNicholson, RRoberts, PSmith, AThe highly diastereoselective anti-aminohydroxylation of alpha,beta-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine, has been used as the key step in the asymmetric synthesis of N,O-diacetyl xestoaminol C (41% yield over 8 steps), N,O,O-triacetyl sphinganine (30% yield over 8 steps) and N,O,O-triacetyl sphingosine (30% yield over 7 steps). |
| spellingShingle | Abraham, E Davies, S Millican, N Nicholson, R Roberts, P Smith, A Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine. |
| title | Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine. |
| title_full | Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine. |
| title_fullStr | Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine. |
| title_full_unstemmed | Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine. |
| title_short | Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine. |
| title_sort | asymmetric synthesis of vicinal amino alcohols xestoaminol c sphinganine and sphingosine |
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