0000000000043009

AUTHOR

Miguel A. Maestro

0000-0001-8922-8033

showing 17 related works from this author

Gold catalyzed stereoselective tandem hydroamination–formal aza-Diels–Alder reaction of propargylic amino esters

2013

A gold-catalyzed tandem intramolecular hydroamination-formal aza-Diels-Alder reaction of propargylic amino esters is described. The overall process leads to the formation of a tetracyclic framework as a single diastereoisomer, with the creation of four bonds and five stereocenters.

Amino estersChemistryStereochemistryMetals and AlloysDiastereomerGeneral ChemistryCatalysisSurfaces Coatings and FilmsElectronic Optical and Magnetic MaterialsStereocenterCatalysisIntramolecular forceMaterials ChemistryCeramics and CompositesStereoselectivityAza-Diels–Alder reactionHydroaminationChemical Communications
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Gold-Catalyzed Intramolecular Hydroamination of o-Alkynylbenzyl Carbamates: A Route to Chiral Fluorinated Isoindoline and Isoquinoline Derivatives

2013

Enantiomerically pure fluorinated isoindoline and dihydroisoquinoline scaffolds have been prepared through a diastereoselective addition of fluorinated nucleophiles to Ellman’s N-(tert-butanesulfinyl)imines followed by a sequence of Sonogashira cross-coupling/gold(I)-catalyzed cycloisomerization of the corresponding carbamate. A more favored 5-exo-dig mechanism was observed mainly due to an electronic effect of the fluorinated group.

Hydrocarbons FluorinatedMolecular StructureChemistryOrganic ChemistrySonogashira couplingStereoisomerismIsoindolineIsoindolesIsoquinolinesBiochemistryMedicinal chemistryCatalysischemistry.chemical_compoundCycloisomerizationNucleophileIntramolecular forceElectronic effectOrganic chemistryHydroaminationCarbamatesGoldPhysical and Theoretical ChemistryIsoquinolineAmines
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ChemInform Abstract: Gold Catalyzed Stereoselective Tandem Hydroamination-Formal Aza-Diels-Alder Reaction of Propargylic Amino Esters.

2013

The overall sequence of the tandem reaction presented here leads to nitrogen-containing tetracycles under formation of 4 bonds and five stereocenters, in most cases as single diastereoisomers.

Cascade reactionAmino estersChemistryStereochemistryDiastereomerAza-Diels–Alder reactionStereoselectivityGeneral MedicineHydroaminationStereocenterCatalysisChemInform
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ChemInform Abstract: An Approach to 2,4-Substituted Pyrazolo[1,5-a]pyridines and Pyrazolo[1,5-a]azepines by Ring-Closing Metathesis.

2014

Based on the title approach, the diastereoselective synthesis of potential peptidomimetics [(XI) and (XIV)] is described.

Ring-closing metathesisPeptidomimeticChemistrySalt metathesis reactionGeneral MedicineCombinatorial chemistryChemInform
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ChemInform Abstract: Intramolecular Michael Reaction of tert-Butylsulfinyl Ketimines: Asymmetric Synthesis of 3-Substituted Indanones.

2012

The reaction proceeds in the presence of the Ruppert—Prakash reagent (Tms-CF3) with either TBAT or TBAF as a base.

ChemistryIntramolecular forceReagentMichael reactionEnantioselective synthesisGeneral MedicineBase (exponentiation)Medicinal chemistryChemInform
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Structure, magnetic properties and nuclease activity of pyridine-2-carbaldehyde thiosemicarbazonecopper(II) complexes.

2008

New complexes of formulae [Cu(HL 2 )(H 2 O)(NO 3 )](NO 3 ) ( 1 ), [{Cu(L 1 )(tfa)} 2 ] ( 2 ), [{Cu(L 1 )} 2 (pz)](ClO 4 ) 2 ( 3 ) and {[{Cu(L 1 )} 2 (dca)](ClO 4 )} n ( 4 ), where HL 1  = pyridine-2-carbaldehyde thiosemicarbazone, HL 2  = pyridine-2-carbaldehyde 4 N -methylthiosemicarbazone, Htfa = trifluoroacetic acid (CF 3 COOH), pz = pyrazine (C 4 H 4 N 2 ) and dca = dicyanamide [N(CN) 2 ] − , have been synthesized and characterized. The crystal structures of these compounds are built up of monomers ( 1 ), dinuclear entities with the metal centers bridged through the non-thiosemicarbazone coligand ( 2 and 3 ) and 1D chains of dimers ( 4 ). In all the cases, square–pyramidal copper(II) io…

ThiosemicarbazonesNucleasebiologyChemistryPyridineschemistry.chemical_elementCrystal structureDNACrystallography X-RayBiochemistryMagnetic susceptibilityCopperInorganic ChemistryMetalCrystallographychemistry.chemical_compoundMagneticsMonomervisual_artbiology.proteinvisual_art.visual_art_mediumOrganometallic CompoundsAntiferromagnetismSemicarbazoneCopperJournal of inorganic biochemistry
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Base-Dependent Stereodivergent Intramolecular Aza-Michael Reaction: Asymmetric Synthesis of 1,3-Disubstituted Isoindolines

2013

The nucleophilic addition (A(N)) / intramolecular aza-Michael reaction (IMAMR) process on Ellman's tert-butylsulfinyl imines, bearing a Michael acceptor in the ortho position, is studied. This reaction affords 1,3-disubstituted isoindolines with a wide range of substituents in good yields and diastereoselectivities. Interestingly, careful choice of the base for the aza-Michael step allows either the cis or the trans diastereoisomers to be exclusively obtained. This stereodivergent cyclization has enabled the synthesis of C2-symmetric bisacetate-substituted isoindolines. In addition, bisacetate isoindolines bearing two well-differentiated ester moieties are also noteworthy because they may a…

chemistry.chemical_classificationheterocyclesOrtho positioncyclizationNucleophilic additionBase (chemistry)Stereochemistryasymmetric synthesisOrganic ChemistryEnantioselective synthesisDiastereomerGeneral ChemistryCatalysischiral auxiliarieschemistryNitrogen atomIntramolecular forceMichael reactionaza-Michael additionChemistry - A European Journal
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(1,3,4‐Oxadiazole)copper(II) Compounds: Dimensionality, Magnetism and Nuclease Activity

2009

The work presented here describes the synthesis of new copper(II) complexes derived from 2-amino-5-(pyridin-2-yl)-1,3,4-oxadiazole (L1) and 2-methylamino-5-(pyridin-2-yl)-1,3,4-oxadiazole (L2) which also incorporate azido (N3 -), thiocyanato (NCS-), cyanato (NCO-), dicyanamido [N(CN)2 -, dca] and malonato (C3H2O4 2-, mal) coligands. Structures of the [Cu(L2)(mal)(H2O)]·2H 2O(1), [{Cu(L2)(mal)}2] (2), [Cu(L 2)2-(NCS)2] (3), [Cu(L1)(NCS) 2]n (4) and [{Cu(L2)}2(dca) 2](ClO4)2·2H2O (5) compounds show the dependence of the dimensionality on parameters such as the type of oxadiazole and coligand utilised, solvents or reaction times. In this sense, 1 and 3 are mononuclear complexes, 2 contains cen…

NucleasebiologyChemistryMagnetismOxadiazoleMineralogychemistry.chemical_elementReflectivityCopperInorganic Chemistrychemistry.chemical_compoundCrystallographyDna cleavagebiology.proteinEuropean Journal of Inorganic Chemistry
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ChemInform Abstract: Gold-Catalyzed Intramolecular Hydroamination of o-Alkynylbenzyl Carbamates: A Route to Chiral Fluorinated Isoindoline and Isoqui…

2013

Title compounds are prepared in enantiomerically pure form by the diastereoselective addition of fluorinated nucleophiles to N-(tert-butanesulfinyl)imines (I) followed by a sequence of Sonogashira cross-coupling/gold(I)-catalyzed cycloisomerization of the corresponding carbamate.

chemistry.chemical_compoundCycloisomerizationNucleophileChemistryIntramolecular forceSonogashira couplingGeneral MedicineHydroaminationIsoindolineIsoquinolineMedicinal chemistryCatalysisChemInform
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Intramolecular Michael reaction of tert-butylsulfinyl ketimines: asymmetric synthesis of 3-substituted indanones.

2011

Aromatic tert-butylsulfinyl ketimines bearing a suitable Michael acceptor at the ortho position readily undergo an intramolecular conjugate addition achieving indanone derivatives in good yields and complete diastereoselectivity.

Ortho positionMolecular StructureStereochemistryChemistryOrganic ChemistryEnantioselective synthesisStereoisomerismBiochemistryMedicinal chemistryIntramolecular forceIndansNitrilesMichael reactionIminesPhysical and Theoretical ChemistryConjugateOrganic letters
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ChemInform Abstract: Base-Dependent Stereodivergent Intramolecular Aza-Michael Reaction: Asymmetric Synthesis of 1,3-Disubstituted Isoindolines.

2014

For the reaction of the compounds (I) the careful choice of the base allows the exclusive formation of either cis or trans diastereoisomer with the exception of the trihalogenates (Ie) and (If), which afford the cis-products regardless of the base used.

ChemistryStereochemistryIntramolecular forceEnantioselective synthesisMichael reactionDiastereomerGeneral MedicineBase (exponentiation)ChemInform
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An Approach to 2,4-Substituted Pyrazolo[1,5-a]pyridines and Pyrazolo[1,5-a]azepines by Ring-Closing Metathesis

2013

The ring-closing metathesis (RCM) reactions of dienylpyrazoles have been employed in the synthesis of pyrazolo[1,5-a]pyridine and pyrazolo[1,5-a]azepine derivatives. Based on this approach, the diastereoselective synthesis of potential peptidomimetics containing four amino acid residues with the second (i+1) and third (i+2) fragments having been substituted by bicyclic frameworks is described.

chemistry.chemical_compoundRing-closing metathesischemistryBicyclic moleculeStereochemistryPeptidomimeticOrganic ChemistryPyridineEnantioselective synthesisPhysical and Theoretical ChemistryAzepineAmino acid residueMetathesisEuropean Journal of Organic Chemistry
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CCDC 841484: Experimental Crystal Structure Determination

2013

Related Article: Santos Fustero, Raquel Román, Amparo Asensio, Miguel A. Maestro, José L. Aceña, Antonio Simón-Fuentes|2013|Eur.J.Org.Chem.|2013|7164|doi:10.1002/ejoc.201300901

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameterscatena-[bis(mu~2~-22'-(cyclohexane-12-diylbis[iminiomethylylidene])diphenolato)-dinitrato-chloro-cerium dichloromethane solvate]Experimental 3D Coordinates
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CCDC 941485: Experimental Crystal Structure Determination

2013

Related Article: Santos Fustero, Raquel Román, Amparo Asensio, Miguel A. Maestro, José L. Aceña, Antonio Simón-Fuentes|2013|Eur.J.Org.Chem.|2013|7164|doi:10.1002/ejoc.201300901

Space GroupCrystallographyCrystal Systemt-Butyl (1-((1-(1-allyl-3-(2-furyl)-1H-pyrazol-5-yl)but-3-en-1-yl)amino)-1-oxopropan-2-yl)carbamateCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 916244: Experimental Crystal Structure Determination

2013

Related Article: Santos Fustero, Ignacio Ibáñez, Pablo Barrio, Miguel A. Maestro, Silvia Catalán|2013|Org.Lett.|15|832|doi:10.1021/ol3035142

Space GroupCrystallographyCrystal Systemt-Butyl 1-(35-difluorobenzyl)-3-(trifluoromethyl)-13-dihydro-2H-isoindole-2-carboxylateCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 935857: Experimental Crystal Structure Determination

2013

Related Article: Santos Fustero, Lidia Herrera, Ruben Lázaro, Elsa Rodríguez, Miguel A. Maestro, Natalia Mateu, Pablo Barrio|2013|Chem.-Eur.J.|19|11776|doi:10.1002/chem.201301591

Space GroupCrystallographyCrystal SystemCrystal StructureEthyl (2-(t-butylsulfinyl)-23-dihydro-1H-isoindol-1-yl)acetateCell ParametersExperimental 3D Coordinates
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CCDC 916245: Experimental Crystal Structure Determination

2013

Related Article: Santos Fustero, Ignacio Ibáñez, Pablo Barrio, Miguel A. Maestro, Silvia Catalán|2013|Org.Lett.|15|832|doi:10.1021/ol3035142

3-(4-Methoxyphenyl)-1-(trifluoromethyl)-1234-tetrahydroisoquinolineSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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