Enantio- and diastereoselective catalytic alkylation reactions with aziridines.
The first asymmetric phase transfer catalyzed alkylation reaction of a range of carbon acids with N-sulfonyl aziridines is reported. When 10 mol % of a cinchona derived quaternary ammonium salt was employed as the catalyst under mildly basic conditions, N-o-(trifluoromethane)benzenesulfonyl aziridin...
| Główni autorzy: | , , |
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| Format: | Journal article |
| Język: | English |
| Wydane: |
2008
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| _version_ | 1826266164585562112 |
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| author | Moss, T Fenwick, DR Dixon, D |
| author_facet | Moss, T Fenwick, DR Dixon, D |
| author_sort | Moss, T |
| collection | OXFORD |
| description | The first asymmetric phase transfer catalyzed alkylation reaction of a range of carbon acids with N-sulfonyl aziridines is reported. When 10 mol % of a cinchona derived quaternary ammonium salt was employed as the catalyst under mildly basic conditions, N-o-(trifluoromethane)benzenesulfonyl aziridine was efficiently ring-opened to afford the amino ethylene products in consistently high yields and high enantioselectivities (up to 97% ee). By employing substituted aziridines in single enantiomeric form, the corresponding enantiopure alkylation products could be obtained with a range of pronucleophiles in high yields and moderate to high diastereoselectivities (up to 30:1 dr). |
| first_indexed | 2024-03-06T20:34:47Z |
| format | Journal article |
| id | oxford-uuid:3241e7b5-b1f9-414b-a4c4-2d2cf6388fb1 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T20:34:47Z |
| publishDate | 2008 |
| record_format | dspace |
| spelling | oxford-uuid:3241e7b5-b1f9-414b-a4c4-2d2cf6388fb12022-03-26T13:12:56ZEnantio- and diastereoselective catalytic alkylation reactions with aziridines.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:3241e7b5-b1f9-414b-a4c4-2d2cf6388fb1EnglishSymplectic Elements at Oxford2008Moss, TFenwick, DRDixon, DThe first asymmetric phase transfer catalyzed alkylation reaction of a range of carbon acids with N-sulfonyl aziridines is reported. When 10 mol % of a cinchona derived quaternary ammonium salt was employed as the catalyst under mildly basic conditions, N-o-(trifluoromethane)benzenesulfonyl aziridine was efficiently ring-opened to afford the amino ethylene products in consistently high yields and high enantioselectivities (up to 97% ee). By employing substituted aziridines in single enantiomeric form, the corresponding enantiopure alkylation products could be obtained with a range of pronucleophiles in high yields and moderate to high diastereoselectivities (up to 30:1 dr). |
| spellingShingle | Moss, T Fenwick, DR Dixon, D Enantio- and diastereoselective catalytic alkylation reactions with aziridines. |
| title | Enantio- and diastereoselective catalytic alkylation reactions with aziridines. |
| title_full | Enantio- and diastereoselective catalytic alkylation reactions with aziridines. |
| title_fullStr | Enantio- and diastereoselective catalytic alkylation reactions with aziridines. |
| title_full_unstemmed | Enantio- and diastereoselective catalytic alkylation reactions with aziridines. |
| title_short | Enantio- and diastereoselective catalytic alkylation reactions with aziridines. |
| title_sort | enantio and diastereoselective catalytic alkylation reactions with aziridines |
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