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https://hdl.handle.net/10316/107444
Title: | (3S,4S)‐N‐substituted‐3,4‐dihydroxypyrrolidines as ligands for the enantioselective Henry reaction | Authors: | Rénio, Márcia R. R. Sousa, Francisco J. P. M. Tavares, Nélia C. T. Valente, Artur J. M. Serra, M. Elisa Silva Murtinho, Dina |
Keywords: | asymmetric catalysis; complex stoichiometry; Henry reaction; pyrrolidines | Issue Date: | 2021 | Publisher: | Wiley Online Library | Project: | 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 |
Serial title, monograph or event: | Applied Organic Chemistry | Volume: | 35 | Issue: | 5 | 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. | URI: | https://hdl.handle.net/10316/107444 | ISSN: | 0268-2605 1099-0739 |
DOI: | 10.1002/aoc.6175 | Rights: | embargoedAccess |
Appears in Collections: | I&D CQC - Artigos em Revistas Internacionais |
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Rénio2021ApplOrganometChem.pdf | 866.27 kB | Adobe PDF | View/Open |
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