The Experts below are selected from a list of 360 Experts worldwide ranked by ideXlab platform
Xingwang Wang - One of the best experts on this subject based on the ideXlab platform.
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organic hydrogen phosphites and hydrogen phosphates catalyzed friedel crafts amidoalkylation of indoles with aryl aldimines
Tetrahedron Letters, 2011Co-Authors: Beilei Wang, Jinxin Zhang, Guogui Liu, Qi Shen, Xingwang WangAbstract:Abstract A highly efficient and selective Friedel–Crafts amidoalkylation reaction of indoles with N-Ts aryl aldimines has been developed utilizing dimethyl hydrogen phosphite or diphenyl hydrogen phosphate as the organocatalysts, providing a facile and cost-effective process for synthesis of 3-indolyl methanamine derivatives in good to excellent yields. This transformation displays a broad substrate scope and wide functional-group tolerability, regardless of the electronic and steric properties of N-Ts aryl aldimines. Given that the developed catalytic Friedel–Crafts amidoalkylation reaction exhibits several salient features such as metal-free catalysis, high efficiency, low cost and mild reaction condition, this process might have practical applications in the synthesis of 3-indolyl methanamine derivatives.
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dinuclear zinc catalyzed asymmetric friedel crafts amidoalkylation of indoles with aryl aldimines
ChemInform, 2011Co-Authors: Beilei Wang, Jinxin Zhang, Guogui Liu, Qi Shen, Teng Liu, Xingwang WangAbstract:Asymmetric Friedel—Crafts amidoalkylation of indoles (I) and (VI) with aryl aldimines (II), (IV) or (VII) is efficiently catalyzed by Trost′s dinuclear zinc—bis(prolinol)phenol complex.
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dinuclear zinc catalyzed asymmetric friedel crafts amidoalkylation of indoles with aryl aldimines
Organic and Biomolecular Chemistry, 2011Co-Authors: Beilei Wang, Jinxin Zhang, Guogui Liu, Qi Shen, Teng Liu, Xingwang WangAbstract:The asymmetric Friedel–Crafts amidoalkylation of indoles with aryl aldimines could be efficiently catalyzed by Trost's bis-ProPhenol dinuclear zinc complexes to attain 3-indolyl methanamine derivatives in good to excellent yields (85–98%) with moderate to high enantiomeric ratios (from 70 : 30 up to 95 : 5 er). Remarkably, this approach provides efficient access to enantiomerically enriched 3-indolyl methanamines, which avoids the formation of the undesirable bis- and tris(indolyl)methanes (BIMs and TIMs) byproduct.
Beilei Wang - One of the best experts on this subject based on the ideXlab platform.
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organic hydrogen phosphites and hydrogen phosphates catalyzed friedel crafts amidoalkylation of indoles with aryl aldimines
Tetrahedron Letters, 2011Co-Authors: Beilei Wang, Jinxin Zhang, Guogui Liu, Qi Shen, Xingwang WangAbstract:Abstract A highly efficient and selective Friedel–Crafts amidoalkylation reaction of indoles with N-Ts aryl aldimines has been developed utilizing dimethyl hydrogen phosphite or diphenyl hydrogen phosphate as the organocatalysts, providing a facile and cost-effective process for synthesis of 3-indolyl methanamine derivatives in good to excellent yields. This transformation displays a broad substrate scope and wide functional-group tolerability, regardless of the electronic and steric properties of N-Ts aryl aldimines. Given that the developed catalytic Friedel–Crafts amidoalkylation reaction exhibits several salient features such as metal-free catalysis, high efficiency, low cost and mild reaction condition, this process might have practical applications in the synthesis of 3-indolyl methanamine derivatives.
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dinuclear zinc catalyzed asymmetric friedel crafts amidoalkylation of indoles with aryl aldimines
ChemInform, 2011Co-Authors: Beilei Wang, Jinxin Zhang, Guogui Liu, Qi Shen, Teng Liu, Xingwang WangAbstract:Asymmetric Friedel—Crafts amidoalkylation of indoles (I) and (VI) with aryl aldimines (II), (IV) or (VII) is efficiently catalyzed by Trost′s dinuclear zinc—bis(prolinol)phenol complex.
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dinuclear zinc catalyzed asymmetric friedel crafts amidoalkylation of indoles with aryl aldimines
Organic and Biomolecular Chemistry, 2011Co-Authors: Beilei Wang, Jinxin Zhang, Guogui Liu, Qi Shen, Teng Liu, Xingwang WangAbstract:The asymmetric Friedel–Crafts amidoalkylation of indoles with aryl aldimines could be efficiently catalyzed by Trost's bis-ProPhenol dinuclear zinc complexes to attain 3-indolyl methanamine derivatives in good to excellent yields (85–98%) with moderate to high enantiomeric ratios (from 70 : 30 up to 95 : 5 er). Remarkably, this approach provides efficient access to enantiomerically enriched 3-indolyl methanamines, which avoids the formation of the undesirable bis- and tris(indolyl)methanes (BIMs and TIMs) byproduct.
Nuria Sotomayor - One of the best experts on this subject based on the ideXlab platform.
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MCDCalc Values for Chemical Reactivity
2019Co-Authors: Paula Carracedo, Esther Lete, Nuria Sotomayor, Eider Aranzamendi, Sonia Arrasate, Mikel Martinez, Carlos Fernandez-lozano, Haralambos Sarimveis, Georgia Tsiliki, Cristian Robert MunteanuAbstract:Data set of MCDCalc Descriptors for Chiral Brønsted Acid-Catalyzed Enantioselective α-Amidoalkylation Reaction
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phenolic activation in chiral bronsted acid catalyzed intramolecular α amidoalkylation reactions for the synthesis of fused isoquinolines
ACS omega, 2017Co-Authors: Eider Aranzamendi, Nuria Sotomayor, Esther LeteAbstract:An organolithium addition–intramolecular α-amidoalkylation sequence on N-phenethylimides has been developed for the synthesis of fused tetrahydroisoquinoline systems using 1,1′-bi-2-naphthol (binol)-derived Bronsted acids. This transformation is the first in which activated benzene derivatives are used as internal nucleophiles, instead of electron-rich heteroaromatics, generating a quaternary stereocenter. Phenolic substitution on the aromatic ring of the phenethylamino moiety and the use of binol-derived N-triflylphosphoramides as catalysts are determinants to achieve reasonable levels of enantioselection, that is, up to 75% enantiomeric excess, in the α-amidoalkylation step. The procedure is complementary to the intermolecular α-amidoalkylation process, as opposite enantiomers are formed, and to the Pictet–Spengler cyclization, which allows the formation of tertiary stereocenters.
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Phenolic Activation in Chiral Brønsted Acid-Catalyzed Intramolecular α‑Amidoalkylation Reactions for the Synthesis of Fused Isoquinolines
2017Co-Authors: Eider Aranzamendi, Nuria Sotomayor, Esther LeteAbstract:An organolithium addition–intramolecular α-amidoalkylation sequence on N-phenethylimides has been developed for the synthesis of fused tetrahydroisoquinoline systems using 1,1′-bi-2-naphthol (binol)-derived Brønsted acids. This transformation is the first in which activated benzene derivatives are used as internal nucleophiles, instead of electron-rich heteroaromatics, generating a quaternary stereocenter. Phenolic substitution on the aromatic ring of the phenethylamino moiety and the use of binol-derived N-triflylphosphoramides as catalysts are determinants to achieve reasonable levels of enantioselection, that is, up to 75% enantiomeric excess, in the α-amidoalkylation step. The procedure is complementary to the intermolecular α-amidoalkylation process, as opposite enantiomers are formed, and to the Pictet–Spengler cyclization, which allows the formation of tertiary stereocenters
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enantioselective intramolecular α amidoalkylation reaction in the synthesis of pyrrolo 2 1 a isoquinolines
Tetrahedron Letters, 2012Co-Authors: Asier Gomezsanjuan, Nuria Sotomayor, Esther LeteAbstract:Abstract BINOL-derived chiral Bronsted acids are capable of carrying out the intramolecular α-amidoalkylation of a tertiary N-acyliminium ions when a methoxylated benzene ring is used as internal π nucleophile. The reaction can be applied to the synthesis of pyrrolo[2,1-a]isoquinolines and use of the sterically congested acid 3e is determinant to obtain good levels of enantioselection.
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Brønsted Acid Catalyzed Enantioselective α-Amidoalkylation in the Synthesis of Isoindoloisoquinolines
The Journal of organic chemistry, 2012Co-Authors: Eider Aranzamendi, Nuria Sotomayor, Esther LeteAbstract:The Parham cyclization–intermolecular α-amidoalkylation sequence results in the facile enantioselective synthesis of 12b-substituted isoindoloisoquinolines (ee up to 95%) using BINOL-derived Bronsted acids. α-Amidoalkylation of indole occurs through the formation of a chiral conjugate base/bicyclic quaternary N-acyliminium ion pair.
Esther Lete - One of the best experts on this subject based on the ideXlab platform.
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MCDCalc Values for Chemical Reactivity
2019Co-Authors: Paula Carracedo, Esther Lete, Nuria Sotomayor, Eider Aranzamendi, Sonia Arrasate, Mikel Martinez, Carlos Fernandez-lozano, Haralambos Sarimveis, Georgia Tsiliki, Cristian Robert MunteanuAbstract:Data set of MCDCalc Descriptors for Chiral Brønsted Acid-Catalyzed Enantioselective α-Amidoalkylation Reaction
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phenolic activation in chiral bronsted acid catalyzed intramolecular α amidoalkylation reactions for the synthesis of fused isoquinolines
ACS omega, 2017Co-Authors: Eider Aranzamendi, Nuria Sotomayor, Esther LeteAbstract:An organolithium addition–intramolecular α-amidoalkylation sequence on N-phenethylimides has been developed for the synthesis of fused tetrahydroisoquinoline systems using 1,1′-bi-2-naphthol (binol)-derived Bronsted acids. This transformation is the first in which activated benzene derivatives are used as internal nucleophiles, instead of electron-rich heteroaromatics, generating a quaternary stereocenter. Phenolic substitution on the aromatic ring of the phenethylamino moiety and the use of binol-derived N-triflylphosphoramides as catalysts are determinants to achieve reasonable levels of enantioselection, that is, up to 75% enantiomeric excess, in the α-amidoalkylation step. The procedure is complementary to the intermolecular α-amidoalkylation process, as opposite enantiomers are formed, and to the Pictet–Spengler cyclization, which allows the formation of tertiary stereocenters.
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Phenolic Activation in Chiral Brønsted Acid-Catalyzed Intramolecular α‑Amidoalkylation Reactions for the Synthesis of Fused Isoquinolines
2017Co-Authors: Eider Aranzamendi, Nuria Sotomayor, Esther LeteAbstract:An organolithium addition–intramolecular α-amidoalkylation sequence on N-phenethylimides has been developed for the synthesis of fused tetrahydroisoquinoline systems using 1,1′-bi-2-naphthol (binol)-derived Brønsted acids. This transformation is the first in which activated benzene derivatives are used as internal nucleophiles, instead of electron-rich heteroaromatics, generating a quaternary stereocenter. Phenolic substitution on the aromatic ring of the phenethylamino moiety and the use of binol-derived N-triflylphosphoramides as catalysts are determinants to achieve reasonable levels of enantioselection, that is, up to 75% enantiomeric excess, in the α-amidoalkylation step. The procedure is complementary to the intermolecular α-amidoalkylation process, as opposite enantiomers are formed, and to the Pictet–Spengler cyclization, which allows the formation of tertiary stereocenters
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enantioselective intramolecular α amidoalkylation reaction in the synthesis of pyrrolo 2 1 a isoquinolines
Tetrahedron Letters, 2012Co-Authors: Asier Gomezsanjuan, Nuria Sotomayor, Esther LeteAbstract:Abstract BINOL-derived chiral Bronsted acids are capable of carrying out the intramolecular α-amidoalkylation of a tertiary N-acyliminium ions when a methoxylated benzene ring is used as internal π nucleophile. The reaction can be applied to the synthesis of pyrrolo[2,1-a]isoquinolines and use of the sterically congested acid 3e is determinant to obtain good levels of enantioselection.
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Brønsted Acid Catalyzed Enantioselective α-Amidoalkylation in the Synthesis of Isoindoloisoquinolines
The Journal of organic chemistry, 2012Co-Authors: Eider Aranzamendi, Nuria Sotomayor, Esther LeteAbstract:The Parham cyclization–intermolecular α-amidoalkylation sequence results in the facile enantioselective synthesis of 12b-substituted isoindoloisoquinolines (ee up to 95%) using BINOL-derived Bronsted acids. α-Amidoalkylation of indole occurs through the formation of a chiral conjugate base/bicyclic quaternary N-acyliminium ion pair.
Vincent Dalla - One of the best experts on this subject based on the ideXlab platform.
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sequential friedel crafts type α amidoalkylation intramolecular hydroarylation distinct advantage of combined tf2nh cationic lau i as a consecutive or binary bicatalytic system
Organic Letters, 2015Co-Authors: Liliana Boiaryna, Mohamed Othman, Mohamed Salah Azizi, Abderrahman El Bouakher, Baptiste Picard, Catherine Taillier, Malika Trabelsiayadi, Vincent DallaAbstract:The combined use of Tf2NH and L(Au)+X– as a dual or binary catalytic system clearly improves the efficiency and enlarges the scope of the tandem intermolecular Friedel–Crafts α-amidoalkylation/intramolecular hydroarylation sequence, compared to an “all gold” multicatalysis approach.
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Sequential Friedel–Crafts-Type α‑Amidoalkylation/Intramolecular Hydroarylation: Distinct Advantage of Combined Tf2NH/Cationic LAu(I) as a Consecutive or Binary Bicatalytic System
2015Co-Authors: Liliana Boiaryna, Mohamed Othman, Mohamed Salah Azizi, Abderrahman El Bouakher, Baptiste Picard, Catherine Taillier, Malika Trabelsi-ayadi, Vincent DallaAbstract:The combined use of Tf2NH and L(Au)+X– as a dual or binary catalytic system clearly improves the efficiency and enlarges the scope of the tandem intermolecular Friedel–Crafts α-amidoalkylation/intramolecular hydroarylation sequence, compared to an “all gold” multicatalysis approach
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dual hard soft gold catalysis intermolecular friedel crafts type α amidoalkylation alkyne hydroarylation sequences by n acyliminium ion chemistry
ChemInform, 2013Co-Authors: Liliana Boiaryna, Vincent Dalla, Catherine Taillier, Mohamed Kamal El Mkaddem, Mohamed OthmanAbstract:Gold catalysts have been applied in cascade-type reactions for the synthesis of different nitrogen-based compounds. The reactions likely proceed by a new gold-catalyzed cascade intermolecular α-amidoalkylation/intramolecular carbocyclization cascade process by unifying both the σ- and π-Lewis acid properties of the gold salts. In the first part of this report we show that the σ-Lewis acidity of gold(I) and gold(III) could be exploited to efficiently catalyze the nucleophilic substitution of various alkoxy- and acetoxylactams. The reaction was found to be applicable to a wide range of cyclic N-acyliminium ion precursors and various nucleophiles, including allyltrimethylsilane, silyl enol ethers, arenes, and active methylene derivatives. As a logical progression of this study, a combined hard/soft binary catalytic gold system was then used to implement an unprecedented tandem intermolecular Friedel-Crafts amidoalkylation/intramolecular hydroarylation sequence allowing an expedient access to new, complex, fused polyheterocyclic structures from trivial materials.
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eco friendly n acyliminium ion chemistry solvent free hntf2 and tipsotf catalyzed α amidoalkylation of silicon based π nucleophiles
Tetrahedron Letters, 2006Co-Authors: Mariejose Tranchant, Charlotte Moine, Raja Ben Othman, Till Bousquet, Mohamed Othman, Vincent DallaAbstract:Abstract The α-amidoalkylation of silicon-based π-nucleophiles is efficiently catalyzed by HNTf 2 or TIPSOTf at very low levels of loading in neat conditions.