Utilize este identificador para referenciar este registo:
https://hdl.handle.net/1822/73187
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Campo DC | Valor | Idioma |
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dc.contributor.author | Freitas, David S. | por |
dc.contributor.author | Sousa, Cristina E. A. | por |
dc.contributor.author | Parente, Joana | por |
dc.contributor.author | Drogalim, Artem | por |
dc.contributor.author | Fortes, A. Gil | por |
dc.contributor.author | Cerqueira, Nuno M. F. S. A. | por |
dc.contributor.author | Rodríguez-Borges, José E. | por |
dc.contributor.author | Alves, Maria José Chão | por |
dc.date.accessioned | 2021-05-31T11:08:03Z | - |
dc.date.issued | 2019 | - |
dc.identifier.issn | 1477-0520 | por |
dc.identifier.uri | https://hdl.handle.net/1822/73187 | - |
dc.description.abstract | This is the first synthetic report of (3S,4R)-dihydroxy-N-alkyl-l-homoprolines described so far. 2,4-O-Benzylidene-d-erythrose was obtained from d-glucose with an improved yield, and then transformed into the title (3S,4R)-dihydroxy-N-alkyl-l-homoprolines, in a two-step strategy, with excellent overall yields. Hydrogenolysis of the benzyl group led to the NH congener. The synthesis of final products from 1,4-lactone intermediates was studied by computational means either under acidic or basic conditions. The theoretical mechanism studies fully explain the experimental results: (a) an equilibrium between l-homoprolines and their bicyclic counterparts is established in acids; (b) the equilibrium suffers a complete displacement towards the l-homoproline side in a basic medium. | eng |
dc.description.sponsorship | We thank the NMR Portuguese network (PTNMR, Bruker Avance III 400-Univ. Minho), and FCT and FEDER (European Fund for Regional Development)-COMPETE-QREN-EU for financial support to CQ/UM. We also thank Search-ON2 for the revitalization of the HPC infrastructure of UMinho, (NORTE-07-0162-FEDER-000086), co-funded by the North Portugal Regional Operational Programme (ON.2-O Novo Norte), under the National Strategic Reference Framework (NSRF), through the European Regional Development Fund (ERDF) and the doctoral scholarship SFRH/BD/87292/2012. | por |
dc.language.iso | eng | por |
dc.publisher | Royal Society of Chemistry | por |
dc.rights | restrictedAccess | por |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | por |
dc.title | (3S,4R)-3,4-Dihydroxy-N-alkyl-l-homoprolines: synthesis and computational mechanistic studies | eng |
dc.type | article | por |
dc.peerreviewed | yes | por |
dc.relation.publisherversion | https://pubs.rsc.org/en/content/articlelanding/2019/ob/c9ob02141h#!divAbstract | por |
oaire.citationStartPage | 10052 | por |
oaire.citationEndPage | 10064 | por |
oaire.citationIssue | 47 | por |
oaire.citationVolume | 17 | por |
dc.identifier.doi | 10.1039/C9OB02141H | por |
dc.date.embargo | 10000-01-01 | - |
dc.identifier.pmid | 31748775 | por |
dc.subject.fos | Ciências Naturais::Ciências Químicas | por |
dc.subject.wos | Science & Technology | por |
sdum.journal | Organic & Biomolecular Chemistry | por |
oaire.version | AM | por |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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Synthesis-2019.pdf Acesso restrito! | Accepted Manuscript | 1,81 MB | Adobe PDF | Ver/Abrir |
Este trabalho está licenciado sob uma Licença Creative Commons