trans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanism
Herein, we report for the first time a “trans-hydroboration–oxidation product” isolated and characterized under traditional hydroboration–oxidation conditions using cholesterol and diosgenin as substrates. These substrates are excellent starting materials because of the rigidity and different struct...
| Những tác giả chính: | , , , , , , , , , , |
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| Định dạng: | Journal article |
| Ngôn ngữ: | English |
| Được phát hành: |
Royal Society of Chemistry
2020
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| _version_ | 1826269052336603136 |
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| author | Hilario-Martínez, JC Murillo, F García-Méndez, J Dzib, E Sandoval-Ramírez, J Muñoz-Hernández, MÁ Bernès, S Kürti, L Duarte Gonzalez, FJ Merino, G Fernández-Herrera, MA |
| author_facet | Hilario-Martínez, JC Murillo, F García-Méndez, J Dzib, E Sandoval-Ramírez, J Muñoz-Hernández, MÁ Bernès, S Kürti, L Duarte Gonzalez, FJ Merino, G Fernández-Herrera, MA |
| author_sort | Hilario-Martínez, JC |
| collection | OXFORD |
| description | Herein, we report for the first time a “trans-hydroboration–oxidation product” isolated and characterized under traditional hydroboration–oxidation conditions using cholesterol and diosgenin as substrates. These substrates are excellent starting materials because of the rigidity and different structural environments around the double bond. Further investigations based on experimental evidence, in conjunction with theoretical studies, indicate that the formation of this trans-species occurs via a retro-hydroboration of the major product to generate the corresponding Δ6-structure and the subsequent hydroboration by the β-face. Besides, the corresponding Markovnikov type products have been isolated in synthetically useful yields. The behavior of the reaction under a range of temperatures is also investigated. |
| first_indexed | 2024-03-06T21:19:01Z |
| format | Journal article |
| id | oxford-uuid:40cd46df-4f24-4ea9-9333-11b2dde0d272 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T21:19:01Z |
| publishDate | 2020 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:40cd46df-4f24-4ea9-9333-11b2dde0d2722022-03-26T14:39:58Ztrans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanismJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:40cd46df-4f24-4ea9-9333-11b2dde0d272EnglishSymplectic ElementsRoyal Society of Chemistry2020Hilario-Martínez, JCMurillo, FGarcía-Méndez, JDzib, ESandoval-Ramírez, JMuñoz-Hernández, MÁBernès, SKürti, LDuarte Gonzalez, FJMerino, GFernández-Herrera, MAHerein, we report for the first time a “trans-hydroboration–oxidation product” isolated and characterized under traditional hydroboration–oxidation conditions using cholesterol and diosgenin as substrates. These substrates are excellent starting materials because of the rigidity and different structural environments around the double bond. Further investigations based on experimental evidence, in conjunction with theoretical studies, indicate that the formation of this trans-species occurs via a retro-hydroboration of the major product to generate the corresponding Δ6-structure and the subsequent hydroboration by the β-face. Besides, the corresponding Markovnikov type products have been isolated in synthetically useful yields. The behavior of the reaction under a range of temperatures is also investigated. |
| spellingShingle | Hilario-Martínez, JC Murillo, F García-Méndez, J Dzib, E Sandoval-Ramírez, J Muñoz-Hernández, MÁ Bernès, S Kürti, L Duarte Gonzalez, FJ Merino, G Fernández-Herrera, MA trans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanism |
| title | trans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanism |
| title_full | trans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanism |
| title_fullStr | trans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanism |
| title_full_unstemmed | trans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanism |
| title_short | trans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanism |
| title_sort | trans hydroboration oxidation products in δ5 steroids via a hydroboration retro hydroboration mechanism |
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