Stereoselective reduction of chiral 2-furoic acid derivatives using group I metals in ammonia
A series of chiral auxiliaries have been attached to 2-furoic acid and 3-methyl-2-furoic acid. The performance of these auxiliaries in the Birch reduction was assessed and it was found that placing a C-3 methyl group on the heterocycle was essential for good stereoselectivity. Using bis(methoxymethy...
| Main Authors: | , , , |
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| Format: | Journal article |
| Language: | English |
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2000
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| _version_ | 1797068968002846720 |
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| author | Donohoe, T Calabrese, A Stevenson, C Ladduwahetty, T |
| author_facet | Donohoe, T Calabrese, A Stevenson, C Ladduwahetty, T |
| author_sort | Donohoe, T |
| collection | OXFORD |
| description | A series of chiral auxiliaries have been attached to 2-furoic acid and 3-methyl-2-furoic acid. The performance of these auxiliaries in the Birch reduction was assessed and it was found that placing a C-3 methyl group on the heterocycle was essential for good stereoselectivity. Using bis(methoxymethyl)pyrrolidine high levels of diastereoselectivity could be obtained with a range of electrophiles. A model is also presented which explains the sense of stereoselectivity displayed by this auxiliary. After reduction, the auxiliaries could be removed by reaction with acid to furnish dihydrofuran-based carboxylic acids with high enantiomeric excess. © The Royal Society of Chemistry 2000. |
| first_indexed | 2024-03-06T22:17:39Z |
| format | Journal article |
| id | oxford-uuid:53f36091-0903-4bfc-847a-45c3f9bb3b00 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T22:17:39Z |
| publishDate | 2000 |
| record_format | dspace |
| spelling | oxford-uuid:53f36091-0903-4bfc-847a-45c3f9bb3b002022-03-26T16:34:47ZStereoselective reduction of chiral 2-furoic acid derivatives using group I metals in ammoniaJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:53f36091-0903-4bfc-847a-45c3f9bb3b00EnglishSymplectic Elements at Oxford2000Donohoe, TCalabrese, AStevenson, CLadduwahetty, TA series of chiral auxiliaries have been attached to 2-furoic acid and 3-methyl-2-furoic acid. The performance of these auxiliaries in the Birch reduction was assessed and it was found that placing a C-3 methyl group on the heterocycle was essential for good stereoselectivity. Using bis(methoxymethyl)pyrrolidine high levels of diastereoselectivity could be obtained with a range of electrophiles. A model is also presented which explains the sense of stereoselectivity displayed by this auxiliary. After reduction, the auxiliaries could be removed by reaction with acid to furnish dihydrofuran-based carboxylic acids with high enantiomeric excess. © The Royal Society of Chemistry 2000. |
| spellingShingle | Donohoe, T Calabrese, A Stevenson, C Ladduwahetty, T Stereoselective reduction of chiral 2-furoic acid derivatives using group I metals in ammonia |
| title | Stereoselective reduction of chiral 2-furoic acid derivatives using group I metals in ammonia |
| title_full | Stereoselective reduction of chiral 2-furoic acid derivatives using group I metals in ammonia |
| title_fullStr | Stereoselective reduction of chiral 2-furoic acid derivatives using group I metals in ammonia |
| title_full_unstemmed | Stereoselective reduction of chiral 2-furoic acid derivatives using group I metals in ammonia |
| title_short | Stereoselective reduction of chiral 2-furoic acid derivatives using group I metals in ammonia |
| title_sort | stereoselective reduction of chiral 2 furoic acid derivatives using group i metals in ammonia |
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