Search results for: Carlos Roque Duarte Correia

Items from 1 to 20 out of 22 results

article

Enantioselective Synthesis of Dihydrobenzofurans, Dihydrobenzosulfones, and Dihydroindoles by Merging One‐pot Intramolecular Heck‐Matsuda Reactions from Anilines with Redox‐Relay Process

Edson Leonardo Scarpa de Souza, Sergei Aleksandrovich Gorbatov, Breno Mendes Pierozzi, João Marcos Batista Junior, more

Chemistry – A European Journal > 30 > 44 > n/a - n/a

A one‐pot tandem process was developed aiming at the concise and expeditious enantioselective synthesis of dihydrobenzofuran, dihydrobenzosulfone, and dihydroindole scaffolds under mild, and open‐flask conditions. This process combines the in situ generation of aryldiazonium salt directly from the anilines in methanol telescoped to an intramolecular Heck‐Matsuda reaction linked to a redox relay process...

article

In Tandem Enantioselective Intramolecular Heck‐Matsuda Reactions directly from Anilines

Tomaz Henrique Duarte Chorro, Edson Leonardo Scarpa de Souza, Otto Daolio Köster, Ellen Christine Polo, more

Advanced Synthesis & Catalysis > 365 > 2 > 211 - 223

A new enantioselective intramolecular strategy for the synthesis of enantioenriched bridged benzoxacines, unsaturated spirobenzofurans, 2,3‐dihydrobenzofuran and 2,3‐indoline acetate scaffolds in a tandem‐like diazotization/Heck‐Matsuda process directly from anilines has been developed. The process combines the in situ diazotization of the aniline, followed by the intramolecular Heck‐Matsuda reaction,...

article

Enantioselective Synthesis of α,β‐Unsaturated Aryl Lactams by Heck‐Matsuda and Heck‐Mizoroki Arylations of Enelactams

Ingredy Bastos Braga, Ricardo Almir Angnes, Emilio Carlos de Lucca Júnior, Ataualpa Albert Carmo Braga, more

European Journal of Organic Chemistry > 2022 > 39 > n/a - n/a

The chiral aryl lactam nucleus is a common motif present in many bioactive natural products and the development of effective enantioselective methodologies for its preparation is of great interest. In this work, we report the synthesis of several enantioenriched aryl lactams in good yields and enantiomeric ratios using a combined strategy employing arenediazonium salts bearing electron‐withdrawing...

article

In Tandem Auto‐Sustainable Enantioselective Heck‐Matsuda Reactions Directly from Anilines

Christian Leonardo Herrera, João Victor Santiago, Julio Cezar Pastre, Carlos Roque Duarte Correia

Advanced Synthesis & Catalysis > 364 > 11 > 1863 - 1872

An in tandem enantioselective Heck‐Matsuda (HM) reaction of cyclic and acyclic olefins directly from anilines is described. The method relies on a process involving the progressive in situ diazotization of the starting anilines followed by a palladium‐catalyzed Heck‐Matsuda arylation using chiral N,N‐ligands. This intermolecular enantioselective HM arylation strategy was applied to the desymmetrization...

article

Enantioselective Heck Arylation of Acyclic Alkenol Aryl Ethers: Synthetic Applications and DFT Investigation of the Stereoselectivity

Ellen Christine Polo, Martí Fernández Wang, Ricardo Almir Angnes, Ataualpa A. C. Braga, more

Advanced Synthesis & Catalysis > 362 > 4 > 884 - 892

Herein we report the enantioselective Heck‐Matsuda arylation of acyclic E and Z‐alkenyl aryl ethers. The reactions were carried out under mild conditions affording the enantioenriched benzyl ethers in a regioselective manner, moderate to good yields (up to 73%), and in good to excellent enantiomeric ratios (up to 97:3). The enantioselective Heck‐Matsuda arylation has shown a broad scope (25 examples),...

article

Chiral N,N Ligands Enabling Palladium‐Catalyzed Enantioselective Intramolecular Heck–Matsuda Carbonylation Reactions by Sequential Migratory and CO Insertions

Rafaela C. Carmona, Otto D. Köster, Carlos Roque Duarte Correia

Angewandte Chemie > 130 > 37 > 12243 - 12246

Unprecedented enantioselective intramolecular Heck carbonylation reactions of arenediazonium salts were enabled by a chiral N,N ligand. This reaction constitutes the first enantioselective Heck carbonylation that proceeds through migratory insertion followed by CO insertion. The enantioenriched functionalized dihydrobenzofurans were obtained in good to high yields and enantiomeric ratios of up to...

article

Chiral N,N Ligands Enabling Palladium‐Catalyzed Enantioselective Intramolecular Heck–Matsuda Carbonylation Reactions by Sequential Migratory and CO Insertions

Rafaela C. Carmona, Otto D. Köster, Carlos Roque Duarte Correia

Angewandte Chemie International Edition > 57 > 37 > 12067 - 12070

article

Enantioselective, Noncovalent, Substrate‐Directable Heck–Matsuda and Oxidative Heck Arylations of Unactivated Five‐Membered Carbocyclic Olefins

Juliana Manso de Oliveira, Ricardo Almir Angnes, Ismat Ullah Khan, Ellen Christine Polo, more

Chemistry – A European Journal > 24 > 45 > 11738 - 11747

Highly diastereo‐ and enantioselective, noncovalent, substrate‐directable Heck desymmetrizations of cyclopentenyl olefins containing hydroxymethyl and carboxylate functional groups are presented. These conformationally unbiased cyclic olefins underwent effective arylations in yields of up to 97 %, diastereoselectivity up to >20:1, and enantiomeric excesses of up to 99 %. Noncovalent directing effects...

article

Graphene oxide nanomaterials for the removal of non-ionic surfactant from water

Patricia Prediger, Thais Cheminski, Tauany de Figueiredo Neves, William Bardelin Nunes, more

Journal of Environmental Chemical Engineering > 2018 > 6 > 1 > 1536-1545

The presence of surfactants in aquatic environment is a major public health concern. Recently, several methods have been developed to remove these compounds, among these are the adsorption processes. The great challenge of this technology is to achieve high removal capacities, fast adsorption and efficient adsorbent recoveries. The aim of our study was to synthesize GO and rGO and use them for non-ionic...

article

Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)‐Verapamil

Caio C. Oliveira, Andreas Pfaltz, Carlos Roque Duarte Correia

Angewandte Chemie International Edition > 54 > 47 > 14036 - 14039

We describe herein a highly regio‐ and enantioselective Pd‐catalyzed Heck arylation of unactivated trisubstituted acyclic olefins to provide all‐carbon quaternary stereogenic centers. Chiral N,N ligands of the pyrimidine‐ and pyrazino‐oxazoline class were developed for that purpose, providing the desired products in good to high yields with enantiomeric ratios up to >99:1. Both linear and branched...

article

Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)‐Verapamil

Caio C. Oliveira, Andreas Pfaltz, Carlos Roque Duarte Correia

Angewandte Chemie > 127 > 47 > 14242 - 14245

article

Construction of 3-arylpropylamines using Heck arylations. The total synthesis of cinacalcet hydrochloride, alverine, and tolpropamine

Patrícia Prediger, Allan Ribeiro da Silva, Carlos Roque Duarte Correia

Tetrahedron > 2014 > 70 > 20 > 3333-3341

New synthetic routes toward the commercial drugs cinacalcet hydrochloride, alverine, and tolpropamine were developed using a Heck–Matsuda arylation as the key-step. Several reaction conditions were evaluated for the Heck–Matsuda reaction using allylamine derivatives and arenediazonium salts. For cinacalcet hydrochloride, N-formylamide provided the best result, furnishing the synthetic target in a...

article

Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines

Patrícia Prediger, Laís Ferreira Barbosa, Yves Génisson, Carlos Roque Duarte Correia

The Journal of Organic Chemistry > 2011 > 76 > 19 > 7737 - 7749

article

The Heck–Matsuda arylation of 2-hetero-substituted acrylates

Francisco de Azambuja, Carlos Roque Duarte Correia

Tetrahedron Letters > 2011 > 52 > 1 > 42-45

The Heck–Matsuda arylation of 2-aza and 2-oxo-substituted acrylates is described. Several reaction conditions were evaluated including the influence of solvents, temperature, catalysts, and stoichiometry. While the oxygenated system was successfully arylated in benzonitrile with Pd ₂ (dba) ₃ as catalyst, the aza-acrylate furnished methoxylated products. The methoxylated products were...

article

Highly Regio- and Stereoselective Heck Reaction of Allylic Esters with Arenediazonium Salts: Application to the Synthesis of Kavalactones

Angélica Venturini Moro, Flávio Sega Pereira Cardoso, Carlos Roque Duarte Correia

Organic Letters > 2009 > 11 > 16 > 3642 - 3645

article

Synthesis of new aza-bicyclic 2-isoxazolines by 1,3-dipolar cycloaddition of endocyclic enecarbamates and enamides with nitrile oxides

Valderes Moraes de Almeida, Rosiel José dos Santos, Alexandre José da Silva Góes, José Gildo de Lima, more

Tetrahedron Letters > 2009 > 50 > 6 > 684-687

Novel aza-bicyclic 2-isoxazolines, 4,5-dihydroisoxazole[5,4-b]pyrrolidines, and 4,5-dihydroisoxazole[5,4-b]piperidines were synthesized in a highly regioselective manner through a 1,3-dipolar cycloaddition reaction of 5- and 6-membered endocyclic enecarbamates and enamides with several nitrile oxides in good to excellent yields. Hydrogenolysis of 5- and 6-membered Cbz-cycloadducts led to secondary...

article

Synthesis of alexine-like compounds from chiral five-membered endocyclic enecarbamates

Marcelo Siqueira Valle, Pascal Retailleau, Carlos Roque Duarte Correia

Tetrahedron Letters > 2008 > 49 > 12 > 1957-1960

Stereoselective syntheses of enantiomerically enriched trihydroxy pyrrolizidine and indolizidines were accomplished from a common chiral endocyclic enecarbamate. The synthetic strategy features an efficient [2+2] cycloaddition of ketenes to the endocyclic enecarbamate and a highly regioselective Baeyer–Villiger oxidation of the intermediate azabicyclic-cyclobutanones. These new heterocycles are compounds...

article

Regio- and Stereoselective Heck Arylations of N -Carbomethoxy- l - 3-Dehydroproline Methyl Ester with Arenediazonium Salts. Total Synthesis of Neuroexcitatory Aryl Kainoids

Kezia Peixoto da Silva, Marla Narciso Godoi, Carlos Roque Duarte Correia

Organic Letters > 2007 > 9 > 15 > 2815 - 2818

article

Continuous chromatographic separation of a baclofen precursor (N-Boc-4-[p-chloro-phenyl]-2-pyrrolidone) in a simulated moving bed using a polysaccharide carbamate as chiral stationary phase

Vinicius de Veredas, Marcos José Sousa Carpes, Carlos Roque Duarte Correia, Cesar Costapinto Santana

Journal of Chromatography A > 2006 > 1119 > 1-2 > 156-162

Liquid chromatography is known as one of the most flexible, efficient and cost-effective methods to resolve racemic mixture in order to attend the growing demand of the pharmaceutical industry for pure enantiomeric compounds. Cellulose tris(3,5-dimethylphenylcarbamate) is frequently used as a stationary phase for enantiomeric separations because of its attractive properties, including high enantioselectivity,...

article

Efficient Heck Arylations of Cyclic and Acyclic Acrylate Derivatives Using Arenediazonium Tetrafluoroborates. A New Synthesis of the Antidepressant Drug (±)-Paroxetine

Julio Cezar Pastre, Carlos Roque Duarte Correia

Organic Letters > 2006 > 8 > 8 > 1657 - 1660

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Keywords

HECK REACTION (5)
PALLADIUM (5)
ASYMMETRIC CATALYSIS (3)
ARENEDIAZONIUM SALTS (2)
DENSITY FUNCTIONAL CALCULATIONS (2)
N,N LIGANDS (2)
VERAPAMIL (2)
(N-BOC-4-[P-CHLORO-PHENYL]-2-PYRROLIDONE) (1)
1,3-DIPOLAR CYCLOADDITION (1)
2-ISOXAZOLINES (1)
ADSORPTION (1)
ALVERINE (1)
ANILINES (1)
ARYLDIAZONIUM SALTS (1)
ASYMMETRISCHE KATALYSE (1)
BINDING (1)
CASCADE REACTIONS (1)
CELLULOSE TRIS(3,5-DIMETHYLPHENYLCARBAMATE) (1)
CINACALCET HYDROCHLORIDE (1)
COMPUTATIONAL METHODS (1)
CONVULSION (1)
DESYMMETRIZATIONS (1)
DFT (1)
DNQX (1)
DYNAMIC NMR (1)
ENAMIDES (1)
ENAMIDES AND ENECARBAMATES (1)
ENANTIOMER SEPARATION (1)
ENANTIOSELECTIVE HECK (1)
ENANTIOSELECTIVE HECK MATSUDA REACTIONS (1)
ENANTIOSELECTIVE HECK REACTIONS (1)
ENANTIOSELECTIVITY (1)
ENDOCYCLIC ENECARBAMATES (1)
ENELACTAMS (1)
GLUTAMATE (1)
GRAPHENE OXIDE (1)
HECK-REAKTION (1)
HECK‐REAKTION (1)
HOMOGENEOUS CATALYSIS (1)
IN SITU ARYLDIAZONIUM SALT FORMATION (1)
IN TANDEM REACTIONS (1)
INTRACEREBROVENTRICULAR ADMINISTRATION (1)
INTRAMOLECULAR HECK REACTIONS (1)
KASKADENREAKTIONEN (1)
MK-801 (1)
N,N-LIGAND (1)
N,N-LIGANDEN (1)
N,N-LIGANDS (1)
N,N LIGANDS (1)
N,N‐LIGANDEN (1)
NITRILE OXIDES (1)
NON-IONIC SURFACTANT (1)
NONCOVALENT INTERACTIONS (1)
ONE POT REACTIONS (1)
ONE-POT PROCESS (1)
OXIDATION (1)
PALLADIUM CATALYSIS (1)
PALLADIUM-KATALYSE (1)
PREPARATIVE CHROMATOGRAPHY (1)
PURIFICATION (1)
QUARTÄRE STEREOZENTREN (1)
QUATERNARY STEREOCENTERS (1)
RECYCLING (1)
ROTATIONAL BARRIER (1)
SMB CHROMATOGRAPHY (1)
TOLPROPAMINE (1)
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Wiley (10)
Elsevier (8)
ACS (4)

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Advanced Synthesis & Catalysis (3)
Organic Letters (3)
Tetrahedron Letters (3)
Angewandte Chemie (2)
Angewandte Chemie International Edition (2)
Chemistry – A European Journal (2)
European Journal of Organic Chemistry (1)
Journal of Chromatography A (1)
Journal of Environmental Chemical Engineering (1)
Journal of Molecular Structure (1)
Pharmacology, Biochemistry and Behavior (1)
Tetrahedron (1)
The Journal of Organic Chemistry (1)
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Search results for: Carlos Roque Duarte Correia

Enantioselective Synthesis of Dihydrobenzofurans, Dihydrobenzosulfones, and Dihydroindoles by Merging One‐pot Intramolecular Heck‐Matsuda Reactions from Anilines with Redox‐Relay Process

In Tandem Enantioselective Intramolecular Heck‐Matsuda Reactions directly from Anilines

Enantioselective Synthesis of α,β‐Unsaturated Aryl Lactams by Heck‐Matsuda and Heck‐Mizoroki Arylations of Enelactams

In Tandem Auto‐Sustainable Enantioselective Heck‐Matsuda Reactions Directly from Anilines

Enantioselective Heck Arylation of Acyclic Alkenol Aryl Ethers: Synthetic Applications and DFT Investigation of the Stereoselectivity

Chiral N,N Ligands Enabling Palladium‐Catalyzed Enantioselective Intramolecular Heck–Matsuda Carbonylation Reactions by Sequential Migratory and CO Insertions

Chiral N,N Ligands Enabling Palladium‐Catalyzed Enantioselective Intramolecular Heck–Matsuda Carbonylation Reactions by Sequential Migratory and CO Insertions

Enantioselective, Noncovalent, Substrate‐Directable Heck–Matsuda and Oxidative Heck Arylations of Unactivated Five‐Membered Carbocyclic Olefins

Graphene oxide nanomaterials for the removal of non-ionic surfactant from water

Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)‐Verapamil

Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)‐Verapamil

Construction of 3-arylpropylamines using Heck arylations. The total synthesis of cinacalcet hydrochloride, alverine, and tolpropamine

Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines

The Heck–Matsuda arylation of 2-hetero-substituted acrylates

Highly Regio- and Stereoselective Heck Reaction of Allylic Esters with Arenediazonium Salts: Application to the Synthesis of Kavalactones

Synthesis of new aza-bicyclic 2-isoxazolines by 1,3-dipolar cycloaddition of endocyclic enecarbamates and enamides with nitrile oxides

Synthesis of alexine-like compounds from chiral five-membered endocyclic enecarbamates

Regio- and Stereoselective Heck Arylations of N -Carbomethoxy- l - 3-Dehydroproline Methyl Ester with Arenediazonium Salts. Total Synthesis of Neuroexcitatory Aryl Kainoids

Continuous chromatographic separation of a baclofen precursor (N-Boc-4-[p-chloro-phenyl]-2-pyrrolidone) in a simulated moving bed using a polysaccharide carbamate as chiral stationary phase

Efficient Heck Arylations of Cyclic and Acyclic Acrylate Derivatives Using Arenediazonium Tetrafluoroborates. A New Synthesis of the Antidepressant Drug (±)-Paroxetine

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