Anton Vidal-ferran - Academia.edu (original) (raw)
Papers by Anton Vidal-ferran
Cheminform, 2010
1999 stereochemistry stereochemistry (general, optical resolution) O 0030
ChemInform, 1999
A Superior, Readily Available Enantiopure Ligand for the Catalytic Enantioselective Addition of D... more A Superior, Readily Available Enantiopure Ligand for the Catalytic Enantioselective Addition of Diethylzinc to α-Substituted Aldehydes.
Tetrahedron, 2015
ABSTRACT Herein is reported the efficient preparation of a set of enantiopure bisphosphine ligand... more ABSTRACT Herein is reported the efficient preparation of a set of enantiopure bisphosphine ligands, whose backbone incorporates an array of diverse crown ethers as distal regulation sites via well-defined supramolecular interactions to tune the catalytic properties of the bisphosphine groups. These new ligands enabled very good catalytic activity in rhodium-mediated asymmetric hydrogenations at low catalyst loadings, while the enantioselectivity remained moderate. Slightly positive regulation effects for the enantioselectivity of the hydrogenation reactions were obtained as a result of the combination of the appropriate bisphosphine ligand and different regulation agents.
Journal of the Chemical Society, Dalton Transactions, 1997
... Valérie Marvaud, Anton Vidal-Ferran, Simon J. Webb and Jeremy KM Sanders ... ing blocks to in... more ... Valérie Marvaud, Anton Vidal-Ferran, Simon J. Webb and Jeremy KM Sanders ... ing blocks to include the diamagnetic d6 ruthenium carbonyl porphyrin 1, and describe the stereospecific templated synthesis via 2 and 3 of the triruthenium complex 4. Ruthenium porphy-rins have ...
ChemInform, 2008
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a Full Text option. The original article is ...
Journal of the Chemical Society, Perkin Transactions 1, 1995
Page 1. J. CHEM. SOC. PERKIN TRANS. 1 1995 2275 Octatetrayne-linked porphyrins: 'str... more Page 1. J. CHEM. SOC. PERKIN TRANS. 1 1995 2275 Octatetrayne-linked porphyrins: 'stretched' cyclic dimers and trimers with very spacious cavities Harry L. Anderson, Christopher J. Walter, Anton Vidal-Ferran, Robert A. Hay ...
Journal of the Chemical Society, Perkin Transactions 2, 1998
... Nick Bampos, Michèle R. Prinsep, Heyong He, Anton Vidal-Ferran, Alan Bashall, Mary McPartlin,... more ... Nick Bampos, Michèle R. Prinsep, Heyong He, Anton Vidal-Ferran, Alan Bashall, Mary McPartlin, Harry Powell and Jeremy KM Sanders. ... 4, p. 12 . 25, RA Abraham, AE Rowan, DA Goff, KE Mansfield and KM Smith, J. Chem. Soc., Perkin Trans. 2, 1989, 1633 RSC . ...
ChemInform, 2008
A family of chiral phosphinooxazolines (12a-e) derived from modular, enantiopure b-amino alcohols... more A family of chiral phosphinooxazolines (12a-e) derived from modular, enantiopure b-amino alcohols has been prepared, and their palladium complexes have been used as chiral mediators in the asymmetric allylic alkylation reaction. The oxazoline moiety in 12 contains a C-4 aryl and a C-5 alkoxymethyl substituent that can be independently optimized for high catalytic activity and enantioselectivity. A methoxymethyl substituent at C-5 has been found to provide the best results in terms of enantioselectivity and activity in the alkylation of a diverse family of allylic substrates under both thermal and microwave-assisted activation. The palladium-phos-phinooxazoline complexes described in this work are remarkably robust, as the enantioselectivity recorded in the asymmetric allylic alkylation remains essentially unchanged in the temperature range between 20 and 130 8C. An unprecedented reversal in enantioselectivity has been observed between 1,3-diphenylallyl and 1,3-dimethylallyl alkylation substrates, and the origin of this behavior has been explained by means of ONIOM QM/MM calculations.
ChemInform, 2009
Exploring Substrate Scope of Shi-Type Epoxidations. -Simultaneous addition of solutions of Oxone ... more Exploring Substrate Scope of Shi-Type Epoxidations. -Simultaneous addition of solutions of Oxone and potassium carbonate to a buffered solution of alkenes in the presence of a fructose diester dihydrate results in efficient enantioselective formation of oxiranes. The pH value is the key parameter for optimal reactions. -(NIETO, N.; MUNSLOW, I. J.; FERNANDEZ-PEREZ, H.; VIDAL-FERRAN*, A.; Synlett 2008, 18, 2856-2858; Inst. Chem. Res. Catalonia, E-43007 Tarragona, Spain; Eng.) -Mais 12-116
Tetrahedron: Asymmetry, 1997
Secondary amines react with (IR,2S)-indene oxide 1 in a completely regioselective manner leading ... more Secondary amines react with (IR,2S)-indene oxide 1 in a completely regioselective manner leading to trans-2-dialkylamino-l-indanols 4a-d in high yield. A Mitsunobu inversion via the corresponding p-nitrobenzoates, followed by reduction with DIBALH leads to the cis-2-dialkylamino-l-indanols 5a-d also in high yield. These two new classes of aminoindanols have been tested as chiral ligands for the enantioselective addition of diethylzinc to both aliphatic and aromatic aldehydes, leading to l-substituted l-propanols with up to 80% e.e. A very simple procedure t-or the enantiomeric enrichment of 1 from 88% to >_99% e.e. is also reported. @ 1997 Elsevier Science Ltd Indene oxide 1, nowadays readily available in enantioenriched form through a manganese-salen catalysed Jacobsen epoxidation, I has gained considerable importance as a chiral starting material. Being a potential precursor to the cis-aminoindanol moiety present in Merck's HIV protease inhibitor Indinavir 2,2 it has also been studied by chemists at Merck and by others as a source of cisaminoalcohols and related species with activity as chiral ligands for enantioselective catalysis.3 N"~OH f~PhH OH . N .... =-" 1 2
Tetrahedron Letters, 1997
A new ligand, (1R,2R)-l-(c/s-2,6-dimethylpiperidino)-l-phenyl-3-trityloxyproixm-2-ol lc, designed... more A new ligand, (1R,2R)-l-(c/s-2,6-dimethylpiperidino)-l-phenyl-3-trityloxyproixm-2-ol lc, designed on the basis of molecular modelling (AM1) studies to increase the energy gap between the re and si attacks in the aminculcohol promoted addition of diethylzinc to benzaldehyde, has been synthesised in 73% overall yield from enanti~nerically pure epoxycinnamyl alcohol. Ligand lc induces the highly enantioselective addition of Et2Zn to a broad range of aromatic and aliphatic aldehydes. © 1997 Elsevier Science Ltd.
Tetrahedron Letters, 2004
Alcohols Q 0230 Boron Trifluoride Induced Reactions of Phenylglycidyl Ethers: A Convenient Synthe... more Alcohols Q 0230 Boron Trifluoride Induced Reactions of Phenylglycidyl Ethers: A Convenient Synthesis of Enantiopure, Stereodefined Fluorohydrins. -Enantiopure O-substituted epoxy alcohols of type (I) and (III) react with BF3·OEt2 with ring-opening to give β-fluoro alcohols completely regio-and diastereoselectively. -(ISLAS-GONZALEZ, G.; PUIGJANER, C.; VIDAL-FERRAN, A.; MOYANO, A.; RIERA, A.; PERICAS*, M. A.; Tetrahedron Lett. 45 (2004) 33, 6337-6341; Dep. Quim. Org., Univ. Barcelona, E-08028 Barcelona, Spain; Eng.) -Mais 46-078
Tetrahedron Letters, 1999
TETRAHEDRONLETTERSTetrahedron Letters 40 (1999) 777-780PergamonThe Dual-Catalyzed (Amino Alcohol/... more TETRAHEDRONLETTERSTetrahedron Letters 40 (1999) 777-780PergamonThe Dual-Catalyzed (Amino Alcohol/Lewis Acid) Enantioselective Addition ofDiethylzinc to N-Diphenyiphosphinoyl IminesCiril Jimeno, Anton Vidal.Ferran, Albert Moyano, Miquel A. Periebs*, Antoni ...
Tetrahedron, 1995
... of 2Aminobenzenel,3dicarbonitriles from ,[3 Unsaturated Ketones or Aldehydes Pedro Victory,*,... more ... of 2Aminobenzenel,3dicarbonitriles from ,[3 Unsaturated Ketones or Aldehydes Pedro Victory,*,t Angel AlvarezLarena,b Gabriel Germain,c Raoui Kessels,a ... for the reaction of propa o nedinitrile and enones with different structu R,,,,R3 ra,, , aract r tics, ot, , onesu , , nour group. ...
Synlett, 2008
... Exploring Substrate Scope of Shi-Type Epoxidations. Natalia Nieto a , Ian J. Munslow a , Héct... more ... Exploring Substrate Scope of Shi-Type Epoxidations. Natalia Nieto a , Ian J. Munslow a , Héctor Fernández-Pérez a , Anton Vidal-Ferran* a,b. ... Eur. J. 2002, 8: 4164. 3b Popa D, Puigjaner C, Gómez M, Benet-Buchholz J, Vidal-Ferran A, Pericàs MA,Adv. Synth. Catal. ...
Organic Letters, 2002
The addition of diethylzinc to dicobalt hexacarbonyl complexes of acetylenes mediated by (R)-2-pi... more The addition of diethylzinc to dicobalt hexacarbonyl complexes of acetylenes mediated by (R)-2-piperidino-1,1,2-triphenylethanol takes place with very high enantioselectivity (96−99% ee) to afford the S enantiomers of dicobalt hexacarbonyl complexes of 1-alkynyl-1-propanols. The utility of this process is exemplified by the development of a short, highly enantioselective (99% ee) synthesis of unnatural incrustoporin.
![Research paper thumbnail of ( S )-2-[( R )-Fluoro(phenyl)methyl]oxirane: A General Reagent for Determining the ee of α-Chiral Amines](https://attachments.academia-assets.com/45373284/thumbnails/1.jpg)
](Organic Letters, 2010
S)-2-[(R)-Fluoro(phenyl)methyl]oxirane is a new, synthetic, yet enantiopure, chiral resolution re... more S)-2-[(R)-Fluoro(phenyl)methyl]oxirane is a new, synthetic, yet enantiopure, chiral resolution reagent, readily obtained from enantiopure (2S,3S)phenylglycidol, that reacts with a variety of r-chiral primary and secondary amines in a straightforward manner through a regioselective ring-opening. Diastereomeric products are easily identified and quantified by 19 F, 1 H, and 13 C NMR and by HPLC, which makes this fluorinated compound a most versatile reagent for the analysis of scalemic mixtures of amines.
New Journal of Chemistry, 1998
A cyclic Zn-porphyrin trimer with ethyne and butadiyne links stabilises the thermodynamically dis... more A cyclic Zn-porphyrin trimer with ethyne and butadiyne links stabilises the thermodynamically disfavoured endo transition state and product of a reversible DielsÈAlder reaction; at 30 ¡C the endo adduct is formed rapidly and almost exclusively. Linear porphyrin dimers containing ...
Cheminform, 2010
1999 stereochemistry stereochemistry (general, optical resolution) O 0030
ChemInform, 1999
A Superior, Readily Available Enantiopure Ligand for the Catalytic Enantioselective Addition of D... more A Superior, Readily Available Enantiopure Ligand for the Catalytic Enantioselective Addition of Diethylzinc to α-Substituted Aldehydes.
Tetrahedron, 2015
ABSTRACT Herein is reported the efficient preparation of a set of enantiopure bisphosphine ligand... more ABSTRACT Herein is reported the efficient preparation of a set of enantiopure bisphosphine ligands, whose backbone incorporates an array of diverse crown ethers as distal regulation sites via well-defined supramolecular interactions to tune the catalytic properties of the bisphosphine groups. These new ligands enabled very good catalytic activity in rhodium-mediated asymmetric hydrogenations at low catalyst loadings, while the enantioselectivity remained moderate. Slightly positive regulation effects for the enantioselectivity of the hydrogenation reactions were obtained as a result of the combination of the appropriate bisphosphine ligand and different regulation agents.
Journal of the Chemical Society, Dalton Transactions, 1997
... Valérie Marvaud, Anton Vidal-Ferran, Simon J. Webb and Jeremy KM Sanders ... ing blocks to in... more ... Valérie Marvaud, Anton Vidal-Ferran, Simon J. Webb and Jeremy KM Sanders ... ing blocks to include the diamagnetic d6 ruthenium carbonyl porphyrin 1, and describe the stereospecific templated synthesis via 2 and 3 of the triruthenium complex 4. Ruthenium porphy-rins have ...
ChemInform, 2008
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a Full Text option. The original article is ...
Journal of the Chemical Society, Perkin Transactions 1, 1995
Page 1. J. CHEM. SOC. PERKIN TRANS. 1 1995 2275 Octatetrayne-linked porphyrins: 'str... more Page 1. J. CHEM. SOC. PERKIN TRANS. 1 1995 2275 Octatetrayne-linked porphyrins: 'stretched' cyclic dimers and trimers with very spacious cavities Harry L. Anderson, Christopher J. Walter, Anton Vidal-Ferran, Robert A. Hay ...
Journal of the Chemical Society, Perkin Transactions 2, 1998
... Nick Bampos, Michèle R. Prinsep, Heyong He, Anton Vidal-Ferran, Alan Bashall, Mary McPartlin,... more ... Nick Bampos, Michèle R. Prinsep, Heyong He, Anton Vidal-Ferran, Alan Bashall, Mary McPartlin, Harry Powell and Jeremy KM Sanders. ... 4, p. 12 . 25, RA Abraham, AE Rowan, DA Goff, KE Mansfield and KM Smith, J. Chem. Soc., Perkin Trans. 2, 1989, 1633 RSC . ...
ChemInform, 2008
A family of chiral phosphinooxazolines (12a-e) derived from modular, enantiopure b-amino alcohols... more A family of chiral phosphinooxazolines (12a-e) derived from modular, enantiopure b-amino alcohols has been prepared, and their palladium complexes have been used as chiral mediators in the asymmetric allylic alkylation reaction. The oxazoline moiety in 12 contains a C-4 aryl and a C-5 alkoxymethyl substituent that can be independently optimized for high catalytic activity and enantioselectivity. A methoxymethyl substituent at C-5 has been found to provide the best results in terms of enantioselectivity and activity in the alkylation of a diverse family of allylic substrates under both thermal and microwave-assisted activation. The palladium-phos-phinooxazoline complexes described in this work are remarkably robust, as the enantioselectivity recorded in the asymmetric allylic alkylation remains essentially unchanged in the temperature range between 20 and 130 8C. An unprecedented reversal in enantioselectivity has been observed between 1,3-diphenylallyl and 1,3-dimethylallyl alkylation substrates, and the origin of this behavior has been explained by means of ONIOM QM/MM calculations.
ChemInform, 2009
Exploring Substrate Scope of Shi-Type Epoxidations. -Simultaneous addition of solutions of Oxone ... more Exploring Substrate Scope of Shi-Type Epoxidations. -Simultaneous addition of solutions of Oxone and potassium carbonate to a buffered solution of alkenes in the presence of a fructose diester dihydrate results in efficient enantioselective formation of oxiranes. The pH value is the key parameter for optimal reactions. -(NIETO, N.; MUNSLOW, I. J.; FERNANDEZ-PEREZ, H.; VIDAL-FERRAN*, A.; Synlett 2008, 18, 2856-2858; Inst. Chem. Res. Catalonia, E-43007 Tarragona, Spain; Eng.) -Mais 12-116
Tetrahedron: Asymmetry, 1997
Secondary amines react with (IR,2S)-indene oxide 1 in a completely regioselective manner leading ... more Secondary amines react with (IR,2S)-indene oxide 1 in a completely regioselective manner leading to trans-2-dialkylamino-l-indanols 4a-d in high yield. A Mitsunobu inversion via the corresponding p-nitrobenzoates, followed by reduction with DIBALH leads to the cis-2-dialkylamino-l-indanols 5a-d also in high yield. These two new classes of aminoindanols have been tested as chiral ligands for the enantioselective addition of diethylzinc to both aliphatic and aromatic aldehydes, leading to l-substituted l-propanols with up to 80% e.e. A very simple procedure t-or the enantiomeric enrichment of 1 from 88% to >_99% e.e. is also reported. @ 1997 Elsevier Science Ltd Indene oxide 1, nowadays readily available in enantioenriched form through a manganese-salen catalysed Jacobsen epoxidation, I has gained considerable importance as a chiral starting material. Being a potential precursor to the cis-aminoindanol moiety present in Merck's HIV protease inhibitor Indinavir 2,2 it has also been studied by chemists at Merck and by others as a source of cisaminoalcohols and related species with activity as chiral ligands for enantioselective catalysis.3 N"~OH f~PhH OH . N .... =-" 1 2
Tetrahedron Letters, 1997
A new ligand, (1R,2R)-l-(c/s-2,6-dimethylpiperidino)-l-phenyl-3-trityloxyproixm-2-ol lc, designed... more A new ligand, (1R,2R)-l-(c/s-2,6-dimethylpiperidino)-l-phenyl-3-trityloxyproixm-2-ol lc, designed on the basis of molecular modelling (AM1) studies to increase the energy gap between the re and si attacks in the aminculcohol promoted addition of diethylzinc to benzaldehyde, has been synthesised in 73% overall yield from enanti~nerically pure epoxycinnamyl alcohol. Ligand lc induces the highly enantioselective addition of Et2Zn to a broad range of aromatic and aliphatic aldehydes. © 1997 Elsevier Science Ltd.
Tetrahedron Letters, 2004
Alcohols Q 0230 Boron Trifluoride Induced Reactions of Phenylglycidyl Ethers: A Convenient Synthe... more Alcohols Q 0230 Boron Trifluoride Induced Reactions of Phenylglycidyl Ethers: A Convenient Synthesis of Enantiopure, Stereodefined Fluorohydrins. -Enantiopure O-substituted epoxy alcohols of type (I) and (III) react with BF3·OEt2 with ring-opening to give β-fluoro alcohols completely regio-and diastereoselectively. -(ISLAS-GONZALEZ, G.; PUIGJANER, C.; VIDAL-FERRAN, A.; MOYANO, A.; RIERA, A.; PERICAS*, M. A.; Tetrahedron Lett. 45 (2004) 33, 6337-6341; Dep. Quim. Org., Univ. Barcelona, E-08028 Barcelona, Spain; Eng.) -Mais 46-078
Tetrahedron Letters, 1999
TETRAHEDRONLETTERSTetrahedron Letters 40 (1999) 777-780PergamonThe Dual-Catalyzed (Amino Alcohol/... more TETRAHEDRONLETTERSTetrahedron Letters 40 (1999) 777-780PergamonThe Dual-Catalyzed (Amino Alcohol/Lewis Acid) Enantioselective Addition ofDiethylzinc to N-Diphenyiphosphinoyl IminesCiril Jimeno, Anton Vidal.Ferran, Albert Moyano, Miquel A. Periebs*, Antoni ...
Tetrahedron, 1995
... of 2Aminobenzenel,3dicarbonitriles from ,[3 Unsaturated Ketones or Aldehydes Pedro Victory,*,... more ... of 2Aminobenzenel,3dicarbonitriles from ,[3 Unsaturated Ketones or Aldehydes Pedro Victory,*,t Angel AlvarezLarena,b Gabriel Germain,c Raoui Kessels,a ... for the reaction of propa o nedinitrile and enones with different structu R,,,,R3 ra,, , aract r tics, ot, , onesu , , nour group. ...
Synlett, 2008
... Exploring Substrate Scope of Shi-Type Epoxidations. Natalia Nieto a , Ian J. Munslow a , Héct... more ... Exploring Substrate Scope of Shi-Type Epoxidations. Natalia Nieto a , Ian J. Munslow a , Héctor Fernández-Pérez a , Anton Vidal-Ferran* a,b. ... Eur. J. 2002, 8: 4164. 3b Popa D, Puigjaner C, Gómez M, Benet-Buchholz J, Vidal-Ferran A, Pericàs MA,Adv. Synth. Catal. ...
Organic Letters, 2002
The addition of diethylzinc to dicobalt hexacarbonyl complexes of acetylenes mediated by (R)-2-pi... more The addition of diethylzinc to dicobalt hexacarbonyl complexes of acetylenes mediated by (R)-2-piperidino-1,1,2-triphenylethanol takes place with very high enantioselectivity (96−99% ee) to afford the S enantiomers of dicobalt hexacarbonyl complexes of 1-alkynyl-1-propanols. The utility of this process is exemplified by the development of a short, highly enantioselective (99% ee) synthesis of unnatural incrustoporin.
Organic Letters, 2010
S)-2-[(R)-Fluoro(phenyl)methyl]oxirane is a new, synthetic, yet enantiopure, chiral resolution re... more S)-2-[(R)-Fluoro(phenyl)methyl]oxirane is a new, synthetic, yet enantiopure, chiral resolution reagent, readily obtained from enantiopure (2S,3S)phenylglycidol, that reacts with a variety of r-chiral primary and secondary amines in a straightforward manner through a regioselective ring-opening. Diastereomeric products are easily identified and quantified by 19 F, 1 H, and 13 C NMR and by HPLC, which makes this fluorinated compound a most versatile reagent for the analysis of scalemic mixtures of amines.
New Journal of Chemistry, 1998
A cyclic Zn-porphyrin trimer with ethyne and butadiyne links stabilises the thermodynamically dis... more A cyclic Zn-porphyrin trimer with ethyne and butadiyne links stabilises the thermodynamically disfavoured endo transition state and product of a reversible DielsÈAlder reaction; at 30 ¡C the endo adduct is formed rapidly and almost exclusively. Linear porphyrin dimers containing ...