The stereoselective birch reduction of pyrroles
The Birch reduction has been applied to electron-deficient pyrroles substituted with a chiral auxiliary at the C-2 position. Using either 8- phenylmenthol or trans-2-(α-cumyl)cyclohexanol (TCC) as auxiliaries, high levels of stereoselectivity were obtained. Moreover, the auxiliary could be removed u...
| Main Authors: | , , |
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| Format: | Journal article |
| Language: | English |
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1999
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| _version_ | 1797089828792172544 |
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| author | Donohoe, T Guyo, P Helliwell, M |
| author_facet | Donohoe, T Guyo, P Helliwell, M |
| author_sort | Donohoe, T |
| collection | OXFORD |
| description | The Birch reduction has been applied to electron-deficient pyrroles substituted with a chiral auxiliary at the C-2 position. Using either 8- phenylmenthol or trans-2-(α-cumyl)cyclohexanol (TCC) as auxiliaries, high levels of stereoselectivity were obtained. Moreover, the auxiliary could be removed using a high-yielding three-step sequence to furnish substituted dehydroproline derivatives with high enantiomeric purity. By choosing either (-)-8-phenylmenthol or (+)-TCC as an auxiliary either enantiomer of the dehydroproline product could be obtained. |
| first_indexed | 2024-03-07T03:09:43Z |
| format | Journal article |
| id | oxford-uuid:b3c50ce8-44ea-45b1-9c73-c248c4c4d38f |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T03:09:43Z |
| publishDate | 1999 |
| record_format | dspace |
| spelling | oxford-uuid:b3c50ce8-44ea-45b1-9c73-c248c4c4d38f2022-03-27T04:21:35ZThe stereoselective birch reduction of pyrrolesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:b3c50ce8-44ea-45b1-9c73-c248c4c4d38fEnglishSymplectic Elements at Oxford1999Donohoe, TGuyo, PHelliwell, MThe Birch reduction has been applied to electron-deficient pyrroles substituted with a chiral auxiliary at the C-2 position. Using either 8- phenylmenthol or trans-2-(α-cumyl)cyclohexanol (TCC) as auxiliaries, high levels of stereoselectivity were obtained. Moreover, the auxiliary could be removed using a high-yielding three-step sequence to furnish substituted dehydroproline derivatives with high enantiomeric purity. By choosing either (-)-8-phenylmenthol or (+)-TCC as an auxiliary either enantiomer of the dehydroproline product could be obtained. |
| spellingShingle | Donohoe, T Guyo, P Helliwell, M The stereoselective birch reduction of pyrroles |
| title | The stereoselective birch reduction of pyrroles |
| title_full | The stereoselective birch reduction of pyrroles |
| title_fullStr | The stereoselective birch reduction of pyrroles |
| title_full_unstemmed | The stereoselective birch reduction of pyrroles |
| title_short | The stereoselective birch reduction of pyrroles |
| title_sort | stereoselective birch reduction of pyrroles |
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