Utilize este identificador para referenciar este registo:
https://hdl.handle.net/10316/107444
Título: | (3S,4S)‐N‐substituted‐3,4‐dihydroxypyrrolidines as ligands for the enantioselective Henry reaction | Autor: | Rénio, Márcia R. R. Sousa, Francisco J. P. M. Tavares, Nélia C. T. Valente, Artur J. M. Serra, M. Elisa Silva Murtinho, Dina |
Palavras-chave: | asymmetric catalysis; complex stoichiometry; Henry reaction; pyrrolidines | Data: | 2021 | Editora: | Wiley Online Library | Projeto: | info:eu-repo/grantAgreement/FCT/POR_CENTRO/PD/BD/128496/2017/PT/Synthesis of chiral ligands and catalysts for Asymmetric transformations 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 info:eu-repo/grantAgreement/FCT/UID/QUI/00313/2020 |
Título da revista, periódico, livro ou evento: | Applied Organic Chemistry | Volume: | 35 | Número: | 5 | Resumo: | 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. | URI: | https://hdl.handle.net/10316/107444 | ISSN: | 0268-2605 1099-0739 |
DOI: | 10.1002/aoc.6175 | Direitos: | embargoedAccess |
Aparece nas coleções: | I&D CQC - Artigos em Revistas Internacionais |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
---|---|---|---|---|
Rénio2021ApplOrganometChem.pdf | 866.27 kB | Adobe PDF | Ver/Abrir |
Citações SCOPUSTM
2
Visto em 14/out/2024
Citações WEB OF SCIENCETM
2
Visto em 2/out/2024
Visualizações de página
111
Visto em 8/out/2024
Downloads
40
Visto em 8/out/2024
Google ScholarTM
Verificar
Altmetric
Altmetric
Este registo está protegido por Licença Creative Commons