0000000001306828
AUTHOR
Marc Montesinos-magraner
showing 29 related works from this author
Organocatalytic Enantioselective Functionalization of Hydroxyquinolines through an Aza-Friedel-Crafts Alkylation with Isatin-derived Ketimines
2018
[EN] A highly enantioselective addition of hydroxyquinolines to isatin-derived ketimines has been realized using a quinine-derived thiourea organocatalyst. The reaction affords chiral 3-amino-2-oxindoles bearing a quinoline moiety with a quaternary stereocenter in high yields (up to 98%) and excellent enantioselectivities (up to 99%). Moreover, we can extend this methodology for the enantioselective functionalization of 5-hydroxyisoquinoline. This methodology represents, to the best of our knowledge, the first enantioselective addition of hydroxyquinolines to imines.
Leaving Group and Regioselectivity Switches in the Aminoalkylation Reaction of Indoles and Related Heterocycles with α-Amido Sulfones
2013
The regioselective aminoalkylation of indoles and related heterocycles with α-amido sulfones under basic conditions has been studied. The reaction that employed the MeMgBr/MgBr2 system provided high yields of 3-(1-carbamoylalkyl)indoles. On the other hand, the reaction that used Cs2CO3 afforded 1-(1-carbamoylalkyl)indoles exclusively in high yields. The first reaction constitutes a switch of the leaving group of the α-amido sulfone in comparison to previously reported reactions between indoles and α-amido sulfones, which provided 3-(1-arylsulfonylalkyl)indoles. The second reaction constitutes a switch in the regioselectivity. The extensions of these C- and N-aminoalkylations starting from p…
Catalytic Enantioselective Friedel–Crafts Reactions of Naphthols and Electron-Rich Phenols
2016
The enantioselective Friedel–Crafts reaction is a powerful tool for the construction of benzylic stereocenters in a stereodefined manner. Significant advances have already been achieved with heteroarenes such as indoles and pyrroles; however, the reaction with homoarenes is less developed. This short review covers the most relevant literature on enantioselective Friedel–Crafts reactions with naphthols and phenols. 1 Introduction 2 Friedel–Crafts Reactions Involving 1,2-Nucleophilic Addition to C=X Bonds 3 Friedel–Crafts Reactions Involving Conjugate Nucleophilic Addition to Electrophilic C=C Bonds 4 Friedel–Crafts Reactions Involving π-Allylic Complexes as Electrophiles 5 ipso-Friedel–Craft…
ChemInform Abstract: Organocatalytic Asymmetric Addition of Naphthols and Electron-Rich Phenols to Isatin-Derived Ketimines: Highly Enantioselective …
2015
A quinine-derived thiourea organocatalyst promoted the highly enantioselective addition of naphthols and activated phenols to ketimines derived from isatins. The reaction afforded chiral 3-amino-2-oxindoles with a quaternary stereocenter in high yields (up to 99 %) with excellent enantioselectivity (up to 99 % ee). To the best of our knowledge, this transformation is the first highly enantioselective addition of naphthols to ketimines.
Enantioselective Friedel-Crafts reaction of hydroxyarenes with nitroenynes to access chiral heterocycles via sequential catalysis
2021
Naphthols, hydroxyindoles and an activated phenol are reacted with differently substituted (E)-nitrobut-1-en-3-ynes using the commercially available Rawal's chiral squaramide. The corresponding β-nitroalkynes were obtained with good yields and excellent enantioselectivities. Moreover, dihydronaphthofurans can be accessed via silver catalysed cyclization in a tandem one-pot procedure, with high preservation of the optical purity.
A Cu-BOX catalysed enantioselective Mukaiyama-aldol reaction with difluorinated silyl enol ethers and acylpyridine
2022
A Cu(II)/BOX complex catalyses the enantioselective addition of difluorinated silyl enol ethers to acylpyridine N-oxides. The reaction provides difluorinated chiral tertiary alcohols of great interest in medicinal chemistry. These compounds are obtained in moderate to excellent yields and with high enantioselectivities. The stereochemical outcome of the reaction has been explained by DFT calculations.
ChemInform Abstract: Organocatalytic Enantioselective Friedel-Crafts Alkylation of 1-Naphthol Derivatives and Activated Phenols with Ethyl Trifluorop…
2016
Financial support from the MINECO [Gobierno de Espana and FEDER (EU)] (CTQ2013-47949-P) and from Generalitat Valenciana (ISIC2012/001) is gratefully acknowledged. M.M.-M. thanks the Universitat de Valencia for a predoctoral grant. C. V. thanks MINECO for JdC contract. Access to NMR and MS facilities from the Servei central de support a la investigacio experimental (SCSIE)-UV is also acknowledged.
Organocatalytic asymmetric addition of naphthols and electron-rich phenols to isatin-derived ketimines: highly enantioselective construction of tetra…
2015
A quinine-derived thiourea organocatalyst promoted the highly enantioselective addition of naphthols and activated phenols to ketimines derived from isatins. The reaction afforded chiral 3-amino-2-oxindoles with a quaternary stereocenter in high yields (up to 99%) with excellent enantioselectivity (up to 99% ee). To the best of our knowledge, this transformation is the first highly enantioselective addition of naphthols to ketimines
Three-Component Synthesis of α-Aminoperoxides Using Primary and Secondary Dialkylzinc Reagents with O2 and α-Amido Sulfones
2020
A straightforward strategy for the synthesis of unprecedented α-aminoperoxides bearing primary and secondary alkylperoxide substituents is described. Commercially available dialkylzinc reagents are oxidized with molecular oxygen and the consequent peroxide species react with stable (hetero)aromatic and aliphatic α-amido sulfones in excellent yields (>90%). The now available α-aminoperoxides are of potential interest in medicinal chemistry, specifically for the synthesis of antimalarial compounds. Moreover, modification of the reaction conditions selectively leads to N,O-acetals in good yields.
Organocatalytic Enantioselective Friedel–Crafts Aminoalkylation of Indoles in the Carbocyclic Ring
2016
The first general catalytic method for the, so far elusive, enantioselective Friedel−Crafts functionalization of indoles in the carbocyclic ring is presented. This transformation contrasts with the usual tendency of these heterocycles to react at the azole ring. For this purpose, the four regioisomeric hydroxy carbocyclic-substituted indoles were reacted with several isatinderived ketimines, using a Cinchona alkaloid-based squaramide, in a low 0.5−5 mol % catalyst loading, as a bifunctional catalyst. This methodology allows the functionalization of indoles in every position of the carbocyclic ring in a regio- and enantioselective fashion, by switching only the position of the hydroxy group …
ChemInform Abstract: Organocatalytic Enantioselective Aza-Friedel-Crafts Reaction of 2-Naphthols with Benzoxathiazine 2,2-Dioxides.
2015
An organocatalytic enantioselective aza-Friedel–Crafts addition of 2-naphthols to benzoxathiazine 2,2-dioxides is described using a quinine-derived bifunctional catalyst. The method allows the use of a wide range of aromatic compounds as nucleophiles, including 1-naphthol and sesamol, and benzoxathiazines 2,2-dioxides, expanding the existing state of the art enantioselective synthesis of aminomethylnaphthol derivatives.
Organocatalytic Enantioselective Friedel-Crafts Alkylation of 1-Naphthol Derivatives and Activated Phenols with Ethyl Trifluoropyruvate
2015
An organocatalytic enantioselective Friedel–Crafts alkylation of a series of substituted 1- naphthol derivatives and activated phenols with ethyl trifluoropyruvate, catalyzed by a quinine-derived squaramide, is presented. Good yields and high to excellent enantioselectivities of the Friedel– Crafts alkylation products were obtained.
ChemInform Abstract: Leaving Group and Regioselectivity Switches in the Aminoalkylation Reaction of Indoles and Related Heterocycles with α-Amido Sul…
2013
Two methods are presented which allow the regioselective C- or N-aminoalkylation of indoles, pyrroles or azaindoles.
ChemInform Abstract: Catalytic Enantioselective Friedel-Crafts Reactions of Naphthols and Electron-Rich Phenols
2016
The enantioselective Friedel–Crafts reaction is a powerful tool for the construction of benzylic stereocenters in a stereodefined manner. Significant advances have already been achieved with heteroarenes such as indoles and pyrroles; however, the reaction with homoarenes is less developed. This short review covers the most relevant literature on enantioselective Friedel–Crafts reactions with naphthols and phenols. 1 Introduction 2 Friedel–Crafts Reactions Involving 1,2-Nucleophilic Addition to C=X Bonds 3 Friedel–Crafts Reactions Involving Conjugate Nucleophilic Addition to Electrophilic C=C Bonds 4 Friedel–Crafts Reactions Involving π-Allylic Complexes as Electrophiles 5 ipso-Friedel–Craft…
(S)-Mandelic acid enolate as a chiral benzoyl anion equivalent for the enantioselective synthesis of non-symmetrically substituted benzoins
2011
A strategy for the enantioselective synthesis of non-symmetrically substituted benzoins from (S)-mandelic acid and aromatic aldehydes has been developed. This strategy is based on a diastereoselective aldol reaction of the lithium enolate of the 1,3-dioxolan-4-one derived from (S)-mandelic acid and pivalaldehyde with aromatic aldehydes, which gives the corresponding aldols in good yields. Subsequent hydroxyl group protection as MEM ethers, basic hydrolysis of the dioxolanone ring, oxidative decarboxylation of the α-hydroxy acid moiety, and hydroxyl group deprotection provides chiral non-symmetrically substituted benzoins with high enantiomeric excesses.
Hydroxy-Directed Enantioselective Hydroxyalkylation in the Carbocyclic Ring of Indoles
2017
[EN] A Cinchona-derived squaramide catalyzes the reaction between hydroxyindoles and isatins leading to enantioenriched indoles substituted in the carbocyclic ring. The reaction proceeds efficiently with differently substituted isatins, yielding the desired products with excellent regioselectivity, good yields, and high enantiocontroi. Moreover, every position of the carbocyclic ring of the indole can be functionalized by using the appropriate starting hydroxyindole. The OH group was removed smoothly upon hydrogenolysis of the corresponding triflate.
Organocatalytic enantioselective aza-Friedel–Crafts reaction of 2-naphthols with benzoxathiazine 2,2-dioxides
2015
An organocatalytic enantioselective aza-Friedel–Crafts addition of 2-naphthols to benzoxathiazine 2,2-dioxides is described using a quinine-derived bifunctional catalyst. The method allows the use of a wide range of aromatic compounds as nucleophiles, including 1-naphthol and sesamol, and benzoxathiazines 2,2-dioxides, expanding the existing state of the art enantioselective synthesis of aminomethylnaphthol derivatives.
Friedel-Crafts Alkylation of Arenes in Total Synthesis
2015
CCDC 1557026: Experimental Crystal Structure Determination
2018
Related Article: Carlos Vila, Alejandra Rendón-Patiño, Marc Montesinos-Magraner, Gonzalo Blay, M. Carmen Muñoz, José R. Pedro|2018|Adv.Synth.Catal.|360|859|doi:10.1002/adsc.201701217
CCDC 1402446: Experimental Crystal Structure Determination
2015
Related Article: Marc Montesinos-Magraner, Rubén Cantón, Carlos Vila, Gonzalo Blay, Isabel Fernández, M. Carmen Muñoz, José R. Pedro|2015|RSC Advances|5|60101|doi:10.1039/C5RA11168D
CCDC 1048103: Experimental Crystal Structure Determination
2015
Related Article: Marc Montesinos-Magraner, Carlos Vila, Rubén Cantón, Gonzalo Blay, Isabel Fernández, M. Carmen Muñoz, José R. Pedro|2015|Angew.Chem.,Int.Ed.|54|6320|doi:10.1002/anie.201501273
CCDC 1402447: Experimental Crystal Structure Determination
2015
Related Article: Marc Montesinos-Magraner, Rubén Cantón, Carlos Vila, Gonzalo Blay, Isabel Fernández, M. Carmen Muñoz, José R. Pedro|2015|RSC Advances|5|60101|doi:10.1039/C5RA11168D
CCDC 1405184: Experimental Crystal Structure Determination
2015
Related Article: Marc Montesinos-Magraner, Carlos Vila, Gonzalo Blay, Isabel Fernández, M. Carmen Muñoz and José R. Pedro|2015|Adv.Synth.Catal.|357|3047|doi:10.1002/adsc.201500548
CCDC 1439710: Experimental Crystal Structure Determination
2016
Related Article: Marc Montesinos-Magraner, Carlos Vila, Alejandra Rendón-Patiño, Gonzalo Blay, Isabel Fernández, M. Carmen Muñoz, and José R. Pedro|2016|ACS Catalysis|6|2689|doi:10.1021/acscatal.6b00260
CCDC 1439713: Experimental Crystal Structure Determination
2016
Related Article: Marc Montesinos-Magraner, Carlos Vila, Alejandra Rendón-Patiño, Gonzalo Blay, Isabel Fernández, M. Carmen Muñoz, and José R. Pedro|2016|ACS Catalysis|6|2689|doi:10.1021/acscatal.6b00260
CCDC 1048104: Experimental Crystal Structure Determination
2015
Related Article: Marc Montesinos-Magraner, Carlos Vila, Rubén Cantón, Gonzalo Blay, Isabel Fernández, M. Carmen Muñoz, José R. Pedro|2015|Angew.Chem.,Int.Ed.|54|6320|doi:10.1002/anie.201501273
CCDC 1439709: Experimental Crystal Structure Determination
2016
Related Article: Marc Montesinos-Magraner, Carlos Vila, Alejandra Rendón-Patiño, Gonzalo Blay, Isabel Fernández, M. Carmen Muñoz, and José R. Pedro|2016|ACS Catalysis|6|2689|doi:10.1021/acscatal.6b00260
CCDC 1530502: Experimental Crystal Structure Determination
2017
Related Article: Marc Montesinos-Magraner, Carlos Vila, Gonzalo Blay, Isabel Fernández, M. Carmen Muñoz, José R. Pedro|2017|Org.Lett.|19|1546|doi:10.1021/acs.orglett.7b00354
CCDC 2190657: Experimental Crystal Structure Determination
2022
Related Article: Amparo Sanz-Marco, Daniel Esperilla, Marc Montesinos-Magraner, Carlos Vila, M. Carmen Muñoz, José R. Pedro, Gonzalo Blay|2022|Org.Biomol.Chem.|21|345|doi:10.1039/D2OB01763F