Síntesis Asimétrica y Catálisis

Otro sitio más de Blogs de la Universidad de Valladolid

Recent papers

Recent papers


R. Sánchez-Molpeceres, L. Martín, N. Esteban, J. A. Miguel, Alicia Maestro, J. M. Andrés.

“Enantioselective Amination of 4-Substituted Pyrazolones Catalyzed by Oxindole-Containing Thioureas and by a Recyclable Linear-Polymer-Supported Analogue in a Continuous Flow Process.”

J. Org. Chem. 2024, 89, 330−344.

DOI: 10.1021/acs.joc.3c02069.


Elena Prieto, Jorge D. Martín, Javier Nieto * and Celia Andrés.

«Enantioselective synthesis of 3-hydroxy- and 3-amino-3-alkynyl-2-oxindoles by the dimethylzinc-mediated addition of terminal alkynes to isatins and isatin-derived ketimines

Org. Biomol. Chem. 2023, 21, 6940-6948.

DOI: 10.1039/D3OB01023F

Marta Gil-Ordóñez, Alicia Maestro, José M. Andrés.

“Access to Spiropyrazolone-Butenolides through NHC-Catalyzed [3+2]-Asymmetric Annulation of 3-Bromoenals and 1H-Pyrazol-4,5-diones.”

J. Org. Chem. 2023, 88, 6890−6900.

DOI: 10.1021/acs.joc.3c00188

Marta Gil-Ordóñez, Laura Martín, Alicia Maestro, José M. Andrés.

«Organocatalytic Asymmetric Synthesis of Oxazolidino Spiropyrazolinones via N,O-acetalization/aza Michael addition domino reaction between N-Boc pyrazolinone ketimines and γ-hydroxyenones.»

Org. Biomol. Chem., 2023, 21, 2361–2369.

DOI: 10.1039/d2ob02290g


Marta Gil-Ordóñez, Camille Aubry, Cristopher Niño, Alicia Maestro, José M. Andrés.

“Squaramide-catalyzed asymmetric Mannich reaction between 1,3-dicarbonyl compounds and pyrazolinone ketimines: a pathway to enantioenriched 4-pyrazolyl- and 4-isoxazolyl-4-aminopyrazolone derivatives.”

Molecules 2022, 27, 6983.

DOI: https://doi.org/10.3390/molecules27206983

Eva Sánchez-Hernández, Celia Andrés-Juan, Laura Buzón-Durán, Adriana Correa-Guimaraes,
Jesús Martín-Gil,* Pablo Martín-Ramos.*

«Antifungal Activity of Methylxanthines against Grapevine Trunk Diseases.»

Agronomy 2022, 12, 885.

DOI: https://doi.org/10.3390/agronomy12040885

M. Gil-Ordóñez, A. Maestro, P. Ortega, P. G. Jambrina, J. M. Andrés.

NHC-Catalysed [3+2]-Asymmetric Annulation between Pyrazolin-4,5-diones and Enals: Synthesis of Novel Spirocyclic Pyrazolone γ-Butyrolactones and Computational Study of Mechanism and Stereoselectivity.”

Org. Chem. Front. 2022, 9, 420-427.

DOI: https://doi.org/10.1039/D1QO01462E

J. M. Pérez de la Lastra, , C. Andrés Juan, F. J. Plou, E. Pérez-Lebeña.

«The Nitration of Proteins, Lipids and DNA by Peroxynitrite Derivatives-Chemistry Involved and Biological Relevance.»

Stresses 2022, 2, 53–64.

DOI: https://doi.org/10.3390/stresses2010005


J. M. Pérez de la Lastra, C. Andrés-Juan, F. J. Plou and E. Pérez-Lebeña.

«Theoretical Three-Dimensional Zinc Complexes with Glutathione, Amino Acids and Flavonoids.»

Stresses 2021, 1, 123–141.

DOI: https://doi.org/10.3390/stresses1030011

E. Sánchez-Hernández, L. Buzón-Durán, C. Andrés-Juan, B. Lorenzo-Vidal, J. Martín-Gil and P. Martín-Ramos.

«Physicochemical Characterization of Crithmum maritimum L. and Daucus carota subsp. gummifer (Syme) Hook.fil. and Their Antimicrobial Activity against Apple Tree and Grapevine Phytopathogens.»

Agronomy 2021, 11, 886.

DOI: https://doi.org/10.3390/agronomy11050886

C. Andrés, J.M. Pérez de la Lastra, F.J. Plou, E. Pérez-Lebeña.

«The Chemistry of Reactive Oxygen Species (ROS) Revisited: Outlining
Their Role in Biological Macromolecules (DNA, Lipids and Proteins) and Induced Pathologies.»

Int. J. Mol. Sci. 2021, 22, 4642.

DOI: https://doi.org/10.3390/ijms22094642

E. Prieto, R. Infante, J. Nieto* and C. Andres*.

«Dimethylzinc-mediated enantioselective addition of terminal
alkynes to 1,2-diketones using perhydro-1,3-benzoxazines as

Org. Biomol. Chem., 2021, 19, 3859-3867.

DOI: https://doi-org.ponton.uva.es/10.1039/D1OB00249J

José Manuel Pérez de la Lastra ,* , Celia Andrés-Juan , Francisco J. Plou and Eduardo Pérez-Lebeña.

«Impact of Zinc, Glutathione, and Polyphenols as Antioxidants
in the Immune Response against SARS-CoV-2.»

Processes 2021, 9, 506.

DOI: https://doi.org/10.3390/pr9030506


L. Martín, A. Maestro, J. M. Andrés, R. Pedrosa.

«Bifunctional thiourea-modified polymers of intrinsic microporosity for enantioselective α-amination of 3-aryl-2-oxindoles in batch and flow Conditions.»

Org. Biomol. Chem. 2020, 18, 9275-9283.

DOI: https://doi.org/10.1039/D0OB01373K

M. Rodríguez-Rodríguez, A. Maestro, J. M. Andrés, R. Pedrosa.

«Supported bifunctional chiral thioureas as catalysts in the synthesis of 3-amino-2-oxindoles through enantioselective aza-Friedel-Crafts reaction. Application in continuous flow processes.»

Adv. Synth. Catal. 2020, 362, 2744– 2754.

DOI: https://doi.org/10.1002/adsc.202000238


Patricia Rodríguez-Ferrer, Daniel Naharro, Alicia Maestro, José M. Andrés, Rafael Pedrosa.

«Chiral Bifunctional Thiosquaramides as Organocatalysts in the Synthesis of Enantioenriched 3,3-Disubstituted Oxindoles.»

Eur. J. Org. Chem. 2019, 6539-6549.

DOI: https://doi.org/10.1002/ejoc.201901327

Patricia Rodríguez-Ferrer, Miguel Sanz-Novo, Alicia Maestro, José M. Andrés, Rafael Pedrosa.

«Synthesis of Enantioenriched 3-Amino-3-substituted oxindoles by Stereoselective Mannich Reaction Catalyzed by Supported Bifunctional Thioureas.»

Adv. Synth. Catal. 2019, 361, 3645– 3655.

DOI: https://doi.org/10.1002/adsc.201900414

María Valle, Laura Martín, Alicia Maestro, José M. Andrés, Rafael Pedrosa.

«Chiral Bifunctional Thioureas and Squaramides Grafted into Old Polymers of Intrinsic Microporosity for Novel Applications.»

Polymers 2019, 11, 13.

DOI: https://doi.org/10.3390/polym11010013

Agustín Gutiérrez-Loriente, Jose Miguel Martín Álvarez, Elena Prieto, Celia Andrés, Javier Nieto.

«Synthesis of Enantiopure Oxygen- and Nitrogen-Containing Heterocycles by Diastereoselective Ring-Closing Metathesis Reaction in Perhydro-1,3-benzoxazine Derivatives.»

Adv. Synth. Catal. 2019, 361, 1042-1063.

DOI: https://doi.org/10.1002/adsc.201801454

J. M. Andrés, A. Maestro, M. Valle, I. Valencia, R. Pedrosa.

«Stereoselective Synthesis of Enantioenriched 2,3,4-Trisubstituted Benzopyrans by Cascade Reactions Catalyzed by Monomeric and Polymeric Recoverable Bifunctional Thioureas and Squaramides.»


ACS Omega 2018, 3, 16591−16600.

DOI: https://doi.org/10.1021/acsomega.8b02302

José M. Andrés, Alicia Maestro, María Valle, Rafael Pedrosa.

«Chiral Bifunctional Thioureas and Squaramides and their Copolymers as Recoverable Organocatalysts. Stereoselective Synthesis of 2-Substituted-4-amino-3-nitro-Benzopyrans and 3-Functionalyzed- 3,4- diamino -4H-Chromenes.»

J. Org. Chem. 2018, 83, 5546-5557.

DOI: https://doi.org/10.1021/acs.joc.8b00567


José M. Andrés, Jorge Losada, Alicia Maestro, Patricia Rodríguez-Ferrer, Rafael Pedrosa.

«Supported and Unsupported Chiral Squaramides as Organocatalysts for Stereoselective Michael Additions: Synthesis of Enantiopure Chromenes and Spirochromanes.»

J. Org. Chem. 2017, 82, 8444−8454.

DOI: https://doi.org/10.1021/acs.joc.7b01177

José M. Andrés, Alicia Maestro, Fernando González, Rafael Pedrosa, María Valle.

«Biodegradable Chitosan-derived Thioureas as Recoverable Supported Organocatalysts. Application to the Stereoselective Aza-Henry Reaction.»

Eur. J. Org. Chem. 2017, 3658-3665.

DOI: https://doi.org/10.1002/ejoc.201700582

Rebeca Infante, José M. Martín-Alvarez, Celia Andrés and Javier Nieto.

«Dimethylzinc-Mediated Addition of Phenylacetylene to alpha-Diketones Catalyzed by Chiral Perhydro-1,3-benzoxazines.»

Organic Letters 2017, 19 (7), 1516–1519.

DOI: https://doi.org/10.1021/acs.orglett.7b00252

José M. Andrés, Miguel González, Alicia Maestro, Daniel Naharro, Rafael Pedrosa.

«Novel Recyclable Chiral Bifunctional Thioureas derived from [60]Fullerene and their use as Highly Efficient Organocatalysts for Asymmetric nitro-Michael Reaction

Eur. J. Org. Chem. 2017, 2683–2691.

DOI: https://doi.org/10.1002/ejoc.201601640


J.M. Andrés; A. Maestro, P. Rodríguez-Ferrer, I. Simón, R. Pedrosa.

«Short Synthesis of Novel Recyclable Chiral Bifunctional Thioureas from Aminoalkyl Polystyrene and their use as Organocatalysts in Stereoselective aza-Henry Reaction

ChemistrySelect, 2016, 5057-61.

DOI: https://doi.org/10.1002/slct.201601213

James O. Guevara-Pulido, José M. Andrés, Deisy P. Ávila and Rafael Pedrosa.*

«Enantioselective Synthesis of Seven-Membered Carbo- and Heterocyles by Organocatalyzed Intramolecular Michael Addition».

RSC Advances, 2016,6, 30166-30169.

DOI: https://doi.org/10.1039/C6RA04198A

José M. Andrés,* M. Ceballos, A. Maestro, I. Sanz, R. Pedrosa.*

«Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions».

Beilstein J. Org. Chem. 2016, 12, 628-635.

DOI: https://doi.org/10.3762/bjoc.12.61

J.M. Andrés; N. de la Cruz, M. Valle, R. Pedrosa.

«Bottom-up Synthesis of Novel Supported Thioureas and Their Use in Enantioselective Solvent-free Aza-Henry and Michael Additions».

ChemPlusChem, 2016,  81, 86-92.

DOI: https://doi.org/10.1002/cplu.201500476


Javier Nieto, Celia Andrés and Alfonso Pérez-Encabo.

«7-Endo selenocyclization reactions on chiral 3-prenyl and 3-cinnamyl-2-hydroxymethylperhydro-1,3-benzoxazine derivatives».

Organic & Biomolecular Chemistry 2015, 13, 9118–9126.

DOI: https://doi.org/10.1039/C5OB01297J

J. O. Guevara-Pulido, J.M. Andrés; R. Pedrosa.

«The Organocatalyzed Domino Michael-Aldol Reaction Revisited. Synthesis of Enantioenriched 3-Hydroxycyclohexanone Derivatives by Reaction of Enals with a,a´-Diaryl-substituted Acetone«.

RSC Advances, 2015, 5, 65975-65981.

DOI: https://doi.org/10.1039/C5RA11215J

R. Pedrosa,* J.M. Andrés,* D. P. Ávila, M. Ceballos and R. Pindado

«Chiral ureas and thioureas supported on polystyrene for enantioselective aza-Henry reactions under solvent-free conditions.»

Green Chem. 2015, 17, 2217-2225.

DOI: https://doi.org/10.1039/C4GC02474E


J. Guevara-Pulido, J.M. Andrés; R. Pedrosa.

«Organocatalytic Domino Michael–Heterocyclization Reaction of alpha,beta-Unsaturated Aldehydes and alpha-Cyano Ketones: Synthesis of Enantioenriched 4,5,6-Trisubstituted 3,4-Dihydropyranones».

Eur. J. Org. Chem. 2014, 8072-8076.

J. Guevara-Pulido, J.M. Andrés; R. Pedrosa.

«One-Pot Sequential Organocatalytic Michael−Tishchenko−Lactonization Reactions. Synthesis of Enantioenriched 4,5,6-Trisubstituted δ-Lactones».

J. Org. Chem. 2014, 79, 8638-8644.

Rebeca Infante, Javier Nieto* and Celia Andrés*

«Tandem diastereo-and Enantioselective preparation of aryl and alkyl cyclopropyl carbinols with three adjacent stereocenters using perhydrobenzoxazines and diethylzinc».

 Org. Biomol. Chem. 2014, 12, 345-354.


R. Pedrosa; J.M. Andrés; A. Gamarra; R. Manzano; C. Pérez-López.

«Novel sulfonylpolystyrene-supported prolinamides as catalysts for enantioselective aldol reaction in water».

Tetrahedron 201369, 10811-10819.

(Artículo destacado en Synfacts, 2014, 10, 222).

R. Pedrosa, J.M Andrés, R. Manzano, C. Pérez-López.

«Novel supported and unsupported prolinamides as organocatalyst for enantioselective cyclization of triketones».

Tetrahedron Letters 2013, 54, 3101-3104.

R. Infante, Y. Hernández, J. Nieto,  C. Andrés.

“Enantioselective One-Pot Catalytic Synthesis of 4,5-Epoxy-3-alkanols and 1-Phenyl-2,3-epoxy-1-alkanols from α,β-Unsaturated Aldehydes”.

European Journal of Organic Chemistry  2013 (22), 4863-4869.


R. Infante, A. Gago, J. Nieto,  C. Andres.

«Enantiocontrolled Synthesis of Tertiary α-Hydroxy-α-ynyl Esters by Dimethylzinc-Mediated Addition of Alkynes to α-Keto Esters».

Advanced Synthesis & Catalysis 2012, 354, 2797-2804.

R. Infante, J. Nieto,  C. Andres.

«Enantioselective addition of dimethylzinc to aldehydes catalyzed by a chiral perhydro-1,3-benzoxazine-based amino alcohol as ligand».

Synthesis 2012, 44, 1343-1348.

A. Maestro, R. Pedrosa, A. Pérez-Encabo, J.J. Pérez-Rueda.

«(-)-8-Amino menthol-derived perhydrobenzoxazines as chiral templates and masked aldehydes in the diastereoselective intermolecular Pausond-Khand reaction».

Tetrahedron 2012, 68, 9293-9300.

Rebeca Infante, Javier Nieto and Celia Andrés.

«Highly Homogeneous Stereocontrolled Construction of Quaternary Hydroxyesters by Addition of Dimethylzinc to alpha-ketoesters promoted by Chiral Perhydrobenzoxazines and B(OEt)3».

Chem. Eur. J. 2012, 18, 4375-4379.

A. Maestro, R. Pedrosa, A. Pérez-Encabo, J.J. Pérez-Rueda

«Studies on the Diastereoselective Intramolecular Pauson-Khand Reaction on Regioisomeric Chiral Perhydrobenzoxazines Derived from (-)-8-Aminomenthol»

Eur. J. Org. Chem. 2012, 1202-1208.


R. Manzano, J. M. Andrés, R. Pedrosa.

“Direct experimental evidences on the epimerization of diastereoisomers in the enantioselective organocatalyzed Michael addition of acetoacetates to nitroolefins.”

Synlet  2011, 2203-2205.    

R. Manzano, J. M. Andrés, R. Alvarez, M. D. Muruzábal, A. Rodríguez de Lera, R. Pedrosa.

“Enantioselective Conjugate Addition of Nitro Compounds to α,β-Unsaturated Ketones. An Experimental and Computational Study”.

Chem. Eur. J.  2011, 17, 5931-5938.                                   

R. Pedrosa, J. M. Andrés, R. Manzano, D. Román, S. Téllez

«Highly Diastereo- and Enantioselective Direct Aldol Reactions Promoted by Novel Benzamidoethyl and Benzamidopropyl Prolinamides in Water».

Org. Biomol. Chem. 2011, 9, 935-940.

R. Infante, J. Nieto, C. Andrés.

“Asymmetric additive-free aryl addition to aldehydes using perhydrobenzoxazines as ligands and boroxins as aryl source”.

Org. Biomol. Chem. 2011, 9, 6691-6699.


Rubén Manzano, José M. Andrés, María D. Muruzábal and Rafael Pedrosa

«Stereocontrolled Construction of Quaternary Stereocenters by Inter- and Intramolecular Nitro-Michael Additions Catalyzed by Bifunctional Thioureas».

Adv. Synth. Catal.  2010, 352, 3364-3372.

R. Pedrosa, J. M. Andrés, R. Manzano, P. Rodríguez

«L-Prolinamides Derived from Chiral and Achiral 1,2-Diamines as Useful Novel Bifunctional Organocatalysts for Direct Diastereo- and Enantioselective Aldol Reaction».

Eur. J. Org. Chem. 2010,  5310-5319 .

R. Manzano, J. M. Andrés, M. D. Muruzábal, R. Pedrosa

«Synthesis of both Enantiomers of Hemiesters by Enantioselective Methanolysis of meso Cyclic Anhydrides Catalyzed by a-Amino Acid-derived Chiral Thioureas».

J. Org. Chem.  2010, 75, 5417-5420.

C. Andrés, R. Infante, J. Nieto.

“Perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol as ligands for the catalytic enantioselective addition of diethylzinc to aldehydes”.

Tetrahedron: Asymmetry 2010, 21, 2230-2237.


C. Andrés, I. González,  J. Nieto, C.D. Rosón.

«Lewis Acid Mediated Diastereoselective Keto-Ene Cyclization on Chiral perhydro-1,3-benzoxazines: Synthesis of Enantiopure cis-3,4-Disubstituted 3-Hidroxypyrrolidines».

Tetrahedron 2009, 65, 9728-9733.

J. M. Andrés, R. Manzano, R. Pedrosa

«Novel Bifunctional Chiral Urea and Thiourea Derivatives as Organocatalysts. Enantioselective Nitro Michael Reaction of Malonates and Diketones».

Chem. Eur. J. 2008, 14, 5116-5119.

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