Please use this identifier to cite or link to this item:
https://hdl.handle.net/10316/107442
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Lopes, Susana M. M. | - |
dc.contributor.author | Santos, Joana R. C. | - |
dc.contributor.author | Pinho e Melo, Teresa M. V. D. | - |
dc.date.accessioned | 2023-07-12T09:43:54Z | - |
dc.date.available | 2023-07-12T09:43:54Z | - |
dc.date.issued | 2021-02-11 | - |
dc.identifier.uri | https://hdl.handle.net/10316/107442 | - |
dc.description.abstract | The chemical behavior of steroidal N-sulfonyl-1-azadienes toward carbonyl compounds, in the presence of pyrrolidine, is described. With aldehydes, these azadienes participate in hetero-Diels-Alder reactions with the in situ generated enamines. The stereoselectivity results from the approach of the dienophiles from the less hindered α-face of the steroid, with the pyrrolidine moiety endo and retention of the enamine trans geometry. This diastereoselective synthetic methodology led to a new class of chiral pentacyclic steroids. Interestingly, the studied steroidal scaffolds follow a different mechanistic pathway with cyclic ketones. They undergo a diastereoselective annulation reaction, under enamine catalysis, affording chiral hexacyclic steroids. | pt |
dc.language.iso | eng | pt |
dc.publisher | Royal Society of Chemistry | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/UIDB/QUI/00313/2020 | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP/00313/2020/PT/Coimbra Chemistry Center | pt |
dc.rights | embargoedAccess | pt |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | pt |
dc.subject.mesh | Alkenes | pt |
dc.subject.mesh | Amines | pt |
dc.subject.mesh | Aza Compounds | pt |
dc.subject.mesh | Catalysis | pt |
dc.subject.mesh | Models, Molecular | pt |
dc.subject.mesh | Molecular Conformation | pt |
dc.subject.mesh | Stereoisomerism | pt |
dc.subject.mesh | Steroids | pt |
dc.title | Reactivity of steroidal 1-azadienes toward enamines: an approach to novel chiral penta- and hexacyclic steroids | pt |
dc.type | article | - |
degois.publication.firstPage | 1122 | pt |
degois.publication.lastPage | 1132 | pt |
degois.publication.issue | 5 | pt |
degois.publication.title | Organic & Biomolecular Chemistry | pt |
dc.peerreviewed | yes | pt |
dc.identifier.doi | 10.1039/d0ob02344b | pt |
degois.publication.volume | 19 | pt |
dc.date.embargo | 2022-02-11 | * |
uc.date.periodoEmbargo | 365 | pt |
item.grantfulltext | open | - |
item.cerifentitytype | Publications | - |
item.languageiso639-1 | en | - |
item.openairetype | article | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.fulltext | Com Texto completo | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.orcid | 0000-0002-1580-5667 | - |
crisitem.author.orcid | 0000-0002-2919-3390 | - |
crisitem.author.orcid | 0000-0003-3256-4954 | - |
Appears in Collections: | I&D CQC - Artigos em Revistas Internacionais |
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File | Description | Size | Format | |
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Lopes2021OrgBiomolChem.pdf | 2.59 MB | Adobe PDF | View/Open |
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