trans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanism

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dc.citation.firstpage12764en_US
dc.citation.journalTitleChemical Scienceen_US
dc.citation.lastpage12768en_US
dc.citation.volumeNumber11en_US
dc.contributor.authorHilario-Martínez, J. Ciciolilen_US
dc.contributor.authorMurillo, Fernandoen_US
dc.contributor.authorGarcía-Méndez, Jairen_US
dc.contributor.authorDzib, Eugeniaen_US
dc.contributor.authorSandoval-Ramírez, Jesúsen_US
dc.contributor.authorMuñoz-Hernández, Miguel Ángelen_US
dc.contributor.authorBernès, Sylvainen_US
dc.contributor.authorKürti, Lászlóen_US
dc.contributor.authorDuarte, Fernandaen_US
dc.contributor.authorMerino, Gabrielen_US
dc.contributor.authorFernández-Herrera, María A.en_US
dc.date.accessioned2021-02-08T18:37:51Zen_US
dc.date.available2021-02-08T18:37:51Zen_US
dc.date.issued2020en_US
dc.description.abstractHerein, 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.en_US
dc.identifier.citationHilario-Martínez, J. Ciciolil, Murillo, Fernando, García-Méndez, Jair, et al.. "trans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanism." <i>Chemical Science,</i> 11, (2020) Royal Society of Chemistry: 12764-12768. https://doi.org/10.1039/D0SC01701A.en_US
dc.identifier.digitald0sc01701aen_US
dc.identifier.doihttps://doi.org/10.1039/D0SC01701Aen_US
dc.identifier.urihttps://hdl.handle.net/1911/109814en_US
dc.language.isoengen_US
dc.publisherRoyal Society of Chemistryen_US
dc.rightsThis article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.en_US
dc.rights.urihttps://creativecommons.org/licenses/by-nc/3.0/en_US
dc.titletrans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanismen_US
dc.typeJournal articleen_US
dc.type.dcmiTexten_US
dc.type.publicationpublisher versionen_US
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