Please use this identifier to cite or link to this item:
https://hdl.handle.net/10316/107444
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Rénio, Márcia R. R. | - |
dc.contributor.author | Sousa, Francisco J. P. M. | - |
dc.contributor.author | Tavares, Nélia C. T. | - |
dc.contributor.author | Valente, Artur J. M. | - |
dc.contributor.author | Serra, M. Elisa Silva | - |
dc.contributor.author | Murtinho, Dina | - |
dc.date.accessioned | 2023-07-12T10:39:01Z | - |
dc.date.available | 2023-07-12T10:39:01Z | - |
dc.date.issued | 2021 | - |
dc.identifier.issn | 0268-2605 | pt |
dc.identifier.issn | 1099-0739 | pt |
dc.identifier.uri | https://hdl.handle.net/10316/107444 | - |
dc.description.abstract | The enantioselective Henry reaction is a very important and useful carbon– carbon bond forming reaction. The execution of this reaction requires the use of efficient chiral catalysts. In this work, in situ formed complexes of N-substituted dihydroxypyrrolidines, chiral ligands derived from L-tartaric acid and amines, were evaluated as catalysts in the enantioselective Henry reaction. The results showed that the nature of the N-substituent on the ligand significantly influences the outcome of the reaction. Best results were obtained using a Cu (II) complex of (3S,4S)-N-benzyl-3,4-dihydroxypyrrolidine, in the presence of DIPEA, for the reaction of aromatic aldehydes with nitromethane, at room temperature, originating products with er up to 92:8 (R:S) and conversions up to 96%. The interaction between the pyrrolidine ligand and the copper ion, in isopropanol, was followed by UV-vis spectrophotometry, showing a 1:1 stoichiometry and a binding constant of 4.4. The results obtained will contribute to the design and development of more efficient chiral catalysts for this type of reaction. | pt |
dc.language.iso | eng | pt |
dc.publisher | Wiley Online Library | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/POR_CENTRO/PD/BD/128496/2017/PT/Synthesis of chiral ligands and catalysts for Asymmetric transformations | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/OE/PD/BD/135494/2018/PT/Development of new catalysts for asymmetric reactions and their application in the total synthesis of biologically active compounds | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/UID/QUI/00313/2020 | pt |
dc.rights | embargoedAccess | pt |
dc.rights.uri | http://creativecommons.org/licenses/by-nc/4.0/ | pt |
dc.subject | asymmetric catalysis | pt |
dc.subject | complex stoichiometry | pt |
dc.subject | Henry reaction | pt |
dc.subject | pyrrolidines | pt |
dc.title | (3S,4S)‐N‐substituted‐3,4‐dihydroxypyrrolidines as ligands for the enantioselective Henry reaction | pt |
dc.type | article | - |
degois.publication.firstPage | e6175 | pt |
degois.publication.issue | 5 | pt |
degois.publication.title | Applied Organic Chemistry | pt |
dc.peerreviewed | yes | pt |
dc.identifier.doi | 10.1002/aoc.6175 | pt |
degois.publication.volume | 35 | pt |
dc.date.embargo | 2022-01-01 | * |
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.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.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.orcid | 0000-0002-5246-4232 | - |
crisitem.author.orcid | 0000-0001-6034-7733 | - |
crisitem.author.orcid | 0000-0002-4612-7686 | - |
crisitem.author.orcid | 0000-0002-4562-7072 | - |
crisitem.author.orcid | 0000-0002-1391-9855 | - |
Appears in Collections: | I&D CQC - Artigos em Revistas Internacionais |
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File | Description | Size | Format | |
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Rénio2021ApplOrganometChem.pdf | 866.27 kB | Adobe PDF | View/Open |
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