Oxidative functionalisation of SuperQuat enamides: Asymmetric synthesis of homochiral 1,2 diols
Homochiral (E)-enamides derived from (S)-4-phenyl-5,5-dimethyl-oxazolidin-2-one undergo highly diastereoselective epoxidation upon treatment with dimethyldioxirane (DMDO). Treatment with m-chloroperbenzoic acid (MCPBA) produces syn-(4S, 1′R,2′)-1′ -acyloxy-2′-hydroxy derivatives with high diastereos...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2003
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| _version_ | 1797099954288721920 |
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| author | Davies, S Key, MS Rodriguez-Solla, H Sanganee, H Savory, E Smith, A |
| author_facet | Davies, S Key, MS Rodriguez-Solla, H Sanganee, H Savory, E Smith, A |
| author_sort | Davies, S |
| collection | OXFORD |
| description | Homochiral (E)-enamides derived from (S)-4-phenyl-5,5-dimethyl-oxazolidin-2-one undergo highly diastereoselective epoxidation upon treatment with dimethyldioxirane (DMDO). Treatment with m-chloroperbenzoic acid (MCPBA) produces syn-(4S, 1′R,2′)-1′ -acyloxy-2′-hydroxy derivatives with high diastereoselectivity, consistent with a mechanism involving initial epoxidation and subsequent in situ S N1 type epoxide opening and trapping with m-chlorobenzoic acid. Reductive cleavage of the isolated 1′-acyloxy-2′-hydroxy derivatives generates 1,2-diols in high yields and in high ee. |
| first_indexed | 2024-03-07T05:30:50Z |
| format | Journal article |
| id | oxford-uuid:e237b8b3-019f-46ad-b63e-1470084d1f79 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:30:50Z |
| publishDate | 2003 |
| record_format | dspace |
| spelling | oxford-uuid:e237b8b3-019f-46ad-b63e-1470084d1f792022-03-27T09:59:33ZOxidative functionalisation of SuperQuat enamides: Asymmetric synthesis of homochiral 1,2 diolsJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:e237b8b3-019f-46ad-b63e-1470084d1f79EnglishSymplectic Elements at Oxford2003Davies, SKey, MSRodriguez-Solla, HSanganee, HSavory, ESmith, AHomochiral (E)-enamides derived from (S)-4-phenyl-5,5-dimethyl-oxazolidin-2-one undergo highly diastereoselective epoxidation upon treatment with dimethyldioxirane (DMDO). Treatment with m-chloroperbenzoic acid (MCPBA) produces syn-(4S, 1′R,2′)-1′ -acyloxy-2′-hydroxy derivatives with high diastereoselectivity, consistent with a mechanism involving initial epoxidation and subsequent in situ S N1 type epoxide opening and trapping with m-chlorobenzoic acid. Reductive cleavage of the isolated 1′-acyloxy-2′-hydroxy derivatives generates 1,2-diols in high yields and in high ee. |
| spellingShingle | Davies, S Key, MS Rodriguez-Solla, H Sanganee, H Savory, E Smith, A Oxidative functionalisation of SuperQuat enamides: Asymmetric synthesis of homochiral 1,2 diols |
| title | Oxidative functionalisation of SuperQuat enamides: Asymmetric synthesis of homochiral 1,2 diols |
| title_full | Oxidative functionalisation of SuperQuat enamides: Asymmetric synthesis of homochiral 1,2 diols |
| title_fullStr | Oxidative functionalisation of SuperQuat enamides: Asymmetric synthesis of homochiral 1,2 diols |
| title_full_unstemmed | Oxidative functionalisation of SuperQuat enamides: Asymmetric synthesis of homochiral 1,2 diols |
| title_short | Oxidative functionalisation of SuperQuat enamides: Asymmetric synthesis of homochiral 1,2 diols |
| title_sort | oxidative functionalisation of superquat enamides asymmetric synthesis of homochiral 1 2 diols |
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