Organolithium-induced alkylative ring opening of aziridines: synthesis of unsaturated amino alcohols and ethers.
Organolithium-induced alkylative ring opening of N-sulfonyl-protected aziridinyl ethers is described. The reactions were efficiently carried out with a variety of organolithiums, providing a promising new strategy to unsaturated amino alcohols and ethers. Cis- and trans-1,4-dimethoxybut-2-ene-derive...
| Main Authors: | , , , |
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| Format: | Journal article |
| Language: | English |
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2006
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| _version_ | 1797104166414319616 |
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| author | Hodgson, D Stefane, B Miles, T Witherington, J |
| author_facet | Hodgson, D Stefane, B Miles, T Witherington, J |
| author_sort | Hodgson, D |
| collection | OXFORD |
| description | Organolithium-induced alkylative ring opening of N-sulfonyl-protected aziridinyl ethers is described. The reactions were efficiently carried out with a variety of organolithiums, providing a promising new strategy to unsaturated amino alcohols and ethers. Cis- and trans-1,4-dimethoxybut-2-ene-derived aziridines were prepared, and their propensity to undergo organolithium- induced alkylative desymmetrization is detailed. Use of a single enantiomer of the latter aziridine provides a route to enantiopure unsaturated amino ethers. |
| first_indexed | 2024-03-07T06:30:01Z |
| format | Journal article |
| id | oxford-uuid:f5ad34e5-cba3-45c1-9da0-a8c030700cb3 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T06:30:01Z |
| publishDate | 2006 |
| record_format | dspace |
| spelling | oxford-uuid:f5ad34e5-cba3-45c1-9da0-a8c030700cb32022-03-27T12:28:58ZOrganolithium-induced alkylative ring opening of aziridines: synthesis of unsaturated amino alcohols and ethers.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:f5ad34e5-cba3-45c1-9da0-a8c030700cb3EnglishSymplectic Elements at Oxford2006Hodgson, DStefane, BMiles, TWitherington, JOrganolithium-induced alkylative ring opening of N-sulfonyl-protected aziridinyl ethers is described. The reactions were efficiently carried out with a variety of organolithiums, providing a promising new strategy to unsaturated amino alcohols and ethers. Cis- and trans-1,4-dimethoxybut-2-ene-derived aziridines were prepared, and their propensity to undergo organolithium- induced alkylative desymmetrization is detailed. Use of a single enantiomer of the latter aziridine provides a route to enantiopure unsaturated amino ethers. |
| spellingShingle | Hodgson, D Stefane, B Miles, T Witherington, J Organolithium-induced alkylative ring opening of aziridines: synthesis of unsaturated amino alcohols and ethers. |
| title | Organolithium-induced alkylative ring opening of aziridines: synthesis of unsaturated amino alcohols and ethers. |
| title_full | Organolithium-induced alkylative ring opening of aziridines: synthesis of unsaturated amino alcohols and ethers. |
| title_fullStr | Organolithium-induced alkylative ring opening of aziridines: synthesis of unsaturated amino alcohols and ethers. |
| title_full_unstemmed | Organolithium-induced alkylative ring opening of aziridines: synthesis of unsaturated amino alcohols and ethers. |
| title_short | Organolithium-induced alkylative ring opening of aziridines: synthesis of unsaturated amino alcohols and ethers. |
| title_sort | organolithium induced alkylative ring opening of aziridines synthesis of unsaturated amino alcohols and ethers |
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