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

Simple item page
dc.citation.firstpage12764
dc.citation.journalTitleChemical Science
dc.citation.lastpage12768
dc.citation.volumeNumber11
dc.contributor.authorHilario-Martínez, J. Ciciolil
dc.contributor.authorMurillo, Fernando
dc.contributor.authorGarcía-Méndez, Jair
dc.contributor.authorDzib, Eugenia
dc.contributor.authorSandoval-Ramírez, Jesús
dc.contributor.authorMuñoz-Hernández, Miguel Ángel
dc.contributor.authorBernès, Sylvain
dc.contributor.authorKürti, László
dc.contributor.authorDuarte, Fernanda
dc.contributor.authorMerino, Gabriel
dc.contributor.authorFernández-Herrera, María A.
dc.date.accessioned2021-02-08T18:37:51Z
dc.date.available2021-02-08T18:37:51Z
dc.date.issued2020
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.
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.
dc.identifier.digitald0sc01701a
dc.identifier.doihttps://doi.org/10.1039/D0SC01701A
dc.identifier.urihttps://hdl.handle.net/1911/109814
dc.language.isoeng
dc.publisherRoyal Society of Chemistry
dc.rightsThis article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.
dc.rights.urihttps://creativecommons.org/licenses/by-nc/3.0/
dc.titletrans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanism
dc.typeJournal article
dc.type.dcmiText
dc.type.publicationpublisher version
Files
Original bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
d0sc01701a.pdf
Size:
692.95 KB
Format:
Adobe Portable Document Format
Download
Collections
Faculty Publications
Chemistry Publications