Stereoselectivity in the birch reduction of 2-furoic acid derivatives
The preparation and Birch reduction of chiral 3-methyl-2-furoic acid derivatives is described. Using a Ca symmetrical amine as a chiral auxiliary, very high levels of sterochemical control could be obtained. Moreover, the auxiliary could be removed conveniently by heating in 6M HCl to liberate a car...
| मुख्य लेखकों: | , , , |
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| स्वरूप: | Journal article |
| भाषा: | English |
| प्रकाशित: |
1998
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| _version_ | 1826289729294827520 |
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| author | Donohoe, T Helliwell, M Stevenson, C Ladduwahetty, T |
| author_facet | Donohoe, T Helliwell, M Stevenson, C Ladduwahetty, T |
| author_sort | Donohoe, T |
| collection | OXFORD |
| description | The preparation and Birch reduction of chiral 3-methyl-2-furoic acid derivatives is described. Using a Ca symmetrical amine as a chiral auxiliary, very high levels of sterochemical control could be obtained. Moreover, the auxiliary could be removed conveniently by heating in 6M HCl to liberate a carboxylic acid of high enantiomeric purity. The relative stereochemistry of the Birch reduced amides (and therefore the absolute stereochemistry of the corresponding acids) was determined unambiguously from an X-ray crystal structure. |
| first_indexed | 2024-03-07T02:33:20Z |
| format | Journal article |
| id | oxford-uuid:a7f7bbed-d40f-4fef-a091-bfecb914f2ea |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T02:33:20Z |
| publishDate | 1998 |
| record_format | dspace |
| spelling | oxford-uuid:a7f7bbed-d40f-4fef-a091-bfecb914f2ea2022-03-27T02:58:07ZStereoselectivity in the birch reduction of 2-furoic acid derivativesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:a7f7bbed-d40f-4fef-a091-bfecb914f2eaEnglishSymplectic Elements at Oxford1998Donohoe, THelliwell, MStevenson, CLadduwahetty, TThe preparation and Birch reduction of chiral 3-methyl-2-furoic acid derivatives is described. Using a Ca symmetrical amine as a chiral auxiliary, very high levels of sterochemical control could be obtained. Moreover, the auxiliary could be removed conveniently by heating in 6M HCl to liberate a carboxylic acid of high enantiomeric purity. The relative stereochemistry of the Birch reduced amides (and therefore the absolute stereochemistry of the corresponding acids) was determined unambiguously from an X-ray crystal structure. |
| spellingShingle | Donohoe, T Helliwell, M Stevenson, C Ladduwahetty, T Stereoselectivity in the birch reduction of 2-furoic acid derivatives |
| title | Stereoselectivity in the birch reduction of 2-furoic acid derivatives |
| title_full | Stereoselectivity in the birch reduction of 2-furoic acid derivatives |
| title_fullStr | Stereoselectivity in the birch reduction of 2-furoic acid derivatives |
| title_full_unstemmed | Stereoselectivity in the birch reduction of 2-furoic acid derivatives |
| title_short | Stereoselectivity in the birch reduction of 2-furoic acid derivatives |
| title_sort | stereoselectivity in the birch reduction of 2 furoic acid derivatives |
| work_keys_str_mv | AT donohoet stereoselectivityinthebirchreductionof2furoicacidderivatives AT helliwellm stereoselectivityinthebirchreductionof2furoicacidderivatives AT stevensonc stereoselectivityinthebirchreductionof2furoicacidderivatives AT ladduwahettyt stereoselectivityinthebirchreductionof2furoicacidderivatives |