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474 results on '"Vidal‐Ferran, Anton"'

7. Separation of Volatile Organic Compounds in TAMOF-1

Author

González-Galán, Carmen, primary, de Fez-Febré, Mabel, additional, Giancola, Stefano, additional, González-Cobos, Jesús, additional, Vidal-Ferran, Anton, additional, Galán-Mascarós, José Ramón, additional, Balestra, Salvador R. G., additional, and Calero, Sofía, additional

Published
2022
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12. Differentiation of Epoxide Enantiomers in the Confined Spaces of an Homochiral Cu(II) MOF by Kinetic Resolution

Author

Cabezas Giménez, Juan José, Lillo, Vanesa, Núñez Rico, José Luis, Corella Ochoa, M. Nieves, Jover Modrego, Jesús, Galán Mascarós, Jose Ramón, and Vidal Ferran, Anton

Subjects
Enantiomers, Quiralitat, Amino acids, Enantiòmers, Aminoàcids, Chirality
Abstract

TAMOF-1, a homochiral metal-organic framework (MOF) constructed from an amino acid derivative and Cu(II), was investigated as a heterogeneous catalyst in kinetic resolutions involving the ring opening of styrene oxide with a set of anilines. The branched products generated from the ring opening of styrene oxide with anilines and the unreacted epoxide were obtained with moderately high enantiomeric excesses. The linear product arising from the attack on the non-benzylic position of styrene oxide underwent a second kinetic resolution by reacting with the epoxide, resulting in an amplification of its final enantiomeric excess and a concomitant formation of an array of isomeric aminodiols. Computational studies confirmed the experimental results, providing a deep understanding of the whole process involving the two successive kinetic resolutions. Furthermore, TAMOF-1 activity was conserved after several catalytic cycles. The ring opening of a mesoepoxide with aniline catalyzed by TAMOF-1 was also studied and moderate enantioselectivities were obtained.

Published
2021

15. A DFT/MM analysis of the effect of ligand substituents on asymmetric hydrogenation catalyzed by rhodium complexes with phosphine-phosphinite ligands

Author

Donald, Steven M.A., Vidal-Ferran, Anton, and Maseras, Feliu

Subjects
Molecular mechanics -- Research, Density functionals -- Research, Hydrogenation -- Observations -- Research, Ligands -- Properties -- Research, Chemistry, Observations, Research, Properties
Abstract

DFT and DFT/MM calculations are carried out on the rate-determining step of the addition of dihydrogen to methyl-(N)-acetylaminoacrylate catalyzed by a rhodium catalyst containing a bidentate phosphine--phosphinite ligand. DFT calculations reproduce the experimental results, while DFT/MM calculations do not. The failure of DFT/MM methods for this particular problem is analyzed through a series of calculations with different partitions between the DFT and MM regions, which show that electronic effects of all ligand substituents considered are critical. The analysis of these electronic effects provides key information on the role of each of the substituents in the outcome of the overall catalytic process. Key words: asymmetric hydrogenation, density functional theory, quantum mechanics/molecular mechanics methods, enantioselectivity. Operant sur la base de la TDF et de la TDF/MM, on a effectue des calculs sur l'etape cinetiquement limitante de l'addition du dihydrogene sur le N-acetylaminoacrylate de methyle, catalysee par un catalyseur de rhodium contenant un ligand phosphine--phosphinite bidentate. Les calculs sur la base de la TDF permettent de reproduire les resultats experimentaux alors que ceux effectues sur la base de la TDF/MM ne le permettent pas. On a analyse les causes de l'echec des methodes TDF/MM dans ce probleme particulier en effectuant une serie de calculs avec differentes partitions entre les regions TDF et MM qui montrent que les effets electroniques de tous les ligands substituants consideres jouent un role critique. L'analyse de ces effets electroniques fournit de l'information pertinente sur le role de chacun de substituants dans le resultat du processus catalytique global. Mots-cles : hydrogenation asymetrique, theorie de la fonctionnelle de la densite, methodes de la mecanique quantique/mecanique moleculaire, enantioselectivite. [Traduit par la Redaction], Introduction Over the past three decades, the field of asymmetric catalysis, in general, and asymmetric hydrogenation, in particular, has received considerable interest in academia with the notable contributions of Knowles, [...]

Published
2009
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16. XBphos-Rh: a halogen-bond assembled supramolecular catalyst† †Electronic supplementary information (ESI) available: Experimental details, spectroscopic and crystallographic data. CCDC 1815870 and 1815871. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc00233a

Author

Carreras, Lucas, Serrano-Torné, Marta, van Leeuwen, Piet W. N. M., and Vidal-Ferran, Anton

Subjects
Chemistry
Abstract

XBphos-Rh constitutes the first example of halogen bonding as the driving force behind the assembly of a transition-metal catalyst for hydroborations., The use of halogen bonding as a tool to construct a catalyst backbone is reported. Specifically, pyridyl- and iodotetrafluoroaryl-substituted phosphines were assembled in the presence of a rhodium(i) precursor to form the corresponding halogen-bonded complex XBphos-Rh. The presence of fluorine substituents at the iodo-containing supramolecular motif was not necessary for halogen bonding to occur due to the template effect exerted by the rhodium center during formation of the halogen-bonded complex. The halogen-bonded supramolecular complexes were successfully tested in the catalytic hydroboration of terminal alkynes.

Published
2018

26. A new family of modular chiral ligands for the catalytic enantioselective reduction of prochiral ketones

Author

Puigjaner, Cristina, Vidal-Ferran, Anton, Moyano, Albert, Pericas, Miquel A., and Riera, Antoni

Subjects
Chemistry, Organic -- Research, Alcohol -- Research, Propanols -- Research, Biological sciences, Chemistry
Abstract

A study concerning the preparation of enantiomerically pure oxazaborolidines from phenylpropanol is presented. Results indicate that a four-step sequence involving alcohol protection and the azido group reduction.

Published
1999

27. Structural Investigations on Enantiopure POP Ligands: a High- Performing POP Ligand for Rhodium-catalysed Hydrogenations

Author

Vidal-Ferran, Anton, Balakrishna, Bugga, and Fernández-Pérez, Héctor

Abstract

A second generation of phosphine–phosphite (P–OP) ligands, incorporating a more sterically bulky phosphite group than previous P–OP ligand designs, gave very efficient catalysts for the Rh‐catalysed asymmetric hydrogenation of a diverse array of substrates (11 examples, 93–99 % ee) containing structurally diverse substituents and chelating groups at the C=C double bond. The presence of the sterically bulky (Sa)‐3,3′‐diphenyl‐5,5′,6,6′,7,7′,8,8′‐octahydro‐[1,1′‐binaphthalene]‐2,2′‐diol‐derived phosphite fragment caused significant increases in enantioselectivity (up to Δee = 58 %), and provided improved results compared to those obtained with the first generation of P–OP‐derived rhodium catalysts {i.e., rhodium complexes incorporating phosphine–phosphite ligands with (Ra)‐ and (Sa)‐BINOL‐derived phosphite groups; BINOL = [1,1′‐binaphthalene]‐2,2′‐diol}. Overall, the optimal ligand L8 provided very high enantioselectivities for a range of structurally diverse olefins (up to 99 % ee).

Published
2019

28. Stepwise approach to bimetalic porphyrin hosts: Spatially enforced coordination of a nickel(II) porphyrin

Author

Vidal-Ferran, Anton, Bampos, Nick, and Sanders, Jeremy K.M>

Subjects
Porphyrins -- Research, Biosynthesis -- Observations, Chemistry, Inorganic -- Observations, Chemistry
Abstract

A stepwise convergent route was used in the synthesis of the Znsub3 1,1,2-trimer Znsub33 and the NiZnsub2 1,1,2-trimer NIZnsub23. Both trimers show larger affinity for PYsub3T, with regard to the linear trimers, providing a thermodynamic force for cyclization of new host molecules, characterized by NMR spectroscopy. A resulting Ni(II) paramagnetic complex was characterized by NMR.

Published
1997

29. Synthesis of a family of fine-tunable new chiral ligands for catalytic asymmetric synthesis. Ligand optimization through the enantioselective addition of diethylzinc to aldehydes

Author

Vidal-Ferran, Anton, Moyano, Albert, Pericas, Miqel A., and Riera, Antoni

Subjects
Chirality -- Analysis, Aldehydes -- Analysis, Enantiomers -- Analysis, Organic compounds -- Synthesis, Biological sciences, Chemistry
Abstract

Identification of the steric bulk of the R-oxy group and the specification of the dialkylamino substituent as a nitrogen-containing six-membered ring as the key parameters for high catalytic activity and enantioselectivity was established. Interactions between the methylene groups alpha to nitrogen with the ethyl group being transferred from zinc to carbonyl group were responsible for the high enantioselectivity.

Published
1997

31. Homochiral Metal–Organic Frameworks for Enantioselective Separations in Liquid Chromatography

Author

Corella-Ochoa, M. Nieves, primary, Tapia, Jesús B., additional, Rubin, Heather N., additional, Lillo, Vanesa, additional, González-Cobos, Jesús, additional, Núñez-Rico, José Luis, additional, Balestra, Salvador R.G., additional, Almora-Barrios, Neyvis, additional, Lledós, Marina, additional, Güell-Bara, Arnau, additional, Cabezas-Giménez, Juanjo, additional, Escudero-Adán, Eduardo C., additional, Vidal-Ferran, Anton, additional, Calero, Sofía, additional, Reynolds, Melissa, additional, Martí-Gastaldo, Carlos, additional, and Galán-Mascarós, José Ramón, additional

Published
2019
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37. Homochiral Metal–Organic Frameworks for Enantioselective Separations in Liquid Chromatography

Author

Corella-Ochoa, M. Nieves, Tapia, Jesús B., Rubin, Heather N., Lillo, Vanesa, González-Cobos, Jesús, Núñez-Rico, José Luis, Balestra, Salvador R.G., Almora-Barrios, Neyvis, Lledós, Marina, Güell-Bara, Arnau, Cabezas-Giménez, Juanjo, Escudero-Adán, Eduardo C., Vidal-Ferran, Anton, Calero, Sofía, Reynolds, Melissa, Martí-Gastaldo, Carlos, and Galán-Mascarós, José Ramón

Abstract

Selective separation of enantiomers is a substantial challenge for the pharmaceutical industry. Chromatography on chiral stationary phases is the standard method, but at a very high cost for industrial-scale purification due to the high cost of the chiral stationary phases. Typically, these materials are poorly robust, expensive to manufacture, and often too specific for a single desired substrate, lacking desirable versatility across different chiral analytes. Here, we disclose a porous, robust homochiral metal–organic framework (MOF), TAMOF-1, built from copper(II) and an affordable linker prepared from natural l-histidine. TAMOF-1has shown to be able to separate a variety of model racemic mixtures, including drugs, in a wide range of solvents of different polarity, outperforming several commercial chiral columns for HPLC separations. Although not exploited in the present article, it is worthy to mention that the preparation of this new material is scalable to the multikilogram scale, opening unprecedented possibilities for low-energy chiral separation at the industrial scale.

Published
2024
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46. Stereoselective Rh Catalyzed Hydrogenative Desymmetriza-tion of Achiral Substituted 1,4-Dienes

Author

Fernández-Pérez, Hector, Lao, Joan R., and Vidal-Ferran, Anton

Abstract

Highly efficient catalytic stereoselective hydrogenative desymmetrization reactions mediated by rhodium complexes derived from enantiopure phosphine-phosphite (POP) ligands are described. The highest performing ligand, which contains a TADDOL-derived phosphite fragment [TADDOL = (2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)], presented excel-lent catalytic properties for the desymmetrization of a set of achiral 1,4-dienes, providing access to the selective formation of a variety of enantioenriched secondary and tertiary alcohols (six examples, up to 92% ee).

Published
2016

47. A Practical Synthesis of Rhodium Precatalysts for Enantioselective

Author

Balakrishna, Bugga and Vidal-Ferran, Anton

Subjects
Asymmetric hydrogenation, kinetic resolution, hydrogenative
Abstract

Herein is described a practical method of preparing enantiopure rhodium(I) complexes that can be used as efficient catalysts for the asymmetric hydrogenation of functionalized alkenes, the hydrogenative kinetic resolution of vinyl sulfoxides and the desymmetrization of meso-dienes. All these rhodium precatalysts incorporate enantiopure phosphine-phosphite (POP) ligands as stereochemical directors of the hydrogenative transformations. The synthetic route starts with the ring-opening of an enantiopure Sharpless epoxy ether with a phosphorus nucleophile followed by isolation of the borane-protected phosphino alcohol derivative by crystallization. The subsequent cleavage of this borane complex, the O-phosphorylation of the resulting phosphino alcohol with the corresponding phosphorus electrophiles (chlorophosphite derivatives), and finally the complexation of the in situ generated POP ligands with [Rh(nbd)2]BF4, followed by crystallization, rendered the target precatalysts.

Published
2016

48. Interfacial charge recombination between [e.sup.-]-Ti[O.sub.2] and the [I.sup.-]/[I.sub.3.sup.-] electrolyte in ruthenium heteroleptic complexes: dye molecular structure-open circuit voltage relationship

Author

Reynal, Anna, Forneli, Amparo, Martinez-Ferrero, Eugenia, Sanchez-Diaz, Antonio, Vidal-Ferran, Anton, O'Regan, Brian C., and Palomares, Emilio

Subjects
Ruthenium -- Chemical properties, Voltage -- Evaluation, Electrolytes -- Composition, Organometallic compounds -- Structure, Organometallic compounds -- Chemical properties, Organometallic compounds -- Electric properties, Chemistry
Abstract

The design, synthesis, and charge recombination of a series of heteroleptic ruthenium(II) polypyridyl complexes containing phenanthroline ligands are reported. The results have significant implications for the future design of new ruthenium heteropelptic complexes.

Published
2008

49. Structural optimization of enantiopure 2-cyclialkylamino-2-aryl-1,1-diphenylethanols as catalytic ligands for enantioselective additions to aldehydes

Author

Rodriguez-Escrich, Sergi, Reddy, Katamreddy Subba, Jimeno, Subba, Colet, Gisela, Rodriguez-Escrich, Carles, Sola, Lluis, Vidal-Ferran, Anton, and Pericas, Miquel A.

Subjects
Aldehydes -- Structure, Ligands -- Structure, Biological sciences, Chemistry
Abstract

The different stages of the structural optimization of a family of modular, enantiopure [beta]-amino alcohol ligands with a common 2-amino-2-aryl-1,1-diphenylethanol skeleton are described. The criteria for the discrimination between analogous, highly enantioselective ligands are discussed.

Published
2008

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