Article
Chemistry, Multidisciplinary
Poorna Chandrasekhar Settipalli, Shaik Anwar
Summary: A [2+2+2] annulation reaction between cyclohexanone, beta-nitrostyrene and 2-arylidene-1,3-indanedione has been successfully carried out to obtain multisubstituted spiro trans-decalinol derivatives at room temperature. This reaction process exhibits high chemical yields and excellent diastereoselectivity, resulting in the formation of multiple bonds and stereocenters through the Michael/nitro-Michael/Aldol process.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Amit Shikari, Koushik Mandal, Deepak Chopra, Subhas Chandra Pan
Summary: A new organocatalytic asymmetric synthesis method has been developed for the synthesis of cyclic acetals with a spirooxindole skeleton. It was found that a bifunctional squaramide catalyst with an adamantyl motif was the most effective in the cascade reaction, providing high diastereo- and enantioselectivities for the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Muhammad Sohail, Fujie Tanaka
Summary: The DYKAT reactions can transform dihydrobenzofuranone derivatives into spirooxindole derivatives with high enantioselectivities and yields, regardless of the stereochemistry of the starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xiu-Ning Hu, Dong-Ping Wu, Ye-Peng Xu, Pei-Qiang Huang
Summary: The first organocatalytic asymmetric synthesis of an advanced intermediate of (+)-sarain A was achieved by combining organocatalytic asymmetric Michael addition reaction and a nitrogen-to-carbon chirality transfer. This method allows for the construction of three chiral centers and chemoselective reduction of a key lactam intermediate, providing a tricyclic intermediate with all necessary functionalities for further elaboration into (+)-sarain A.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Martina Sotolova, Martin Kamlar, Marek Remes, Pierre-Yves Geant, Ivana Cisarova, Martin Sticha, Jan Vesely
Summary: An organocatalytic asymmetric domino Michael/alpha-alkylation reaction has been developed for the synthesis of 1,2,3-trisubstituted cyclopentane carbaldehydes. The reaction, catalyzed by chiral secondary amines, exhibits high diastereo- and enantioselectivities.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Wei Liu, Tianren Qin, Wansen Xie, Jinmiao Zhou, Zidan Ye, Xiaoyu Yang
Summary: We have developed an efficient modular asymmetric synthesis of azahelicenes from readily available polycyclic aromatic amines, aldehydes, and (di)enamides, employing a central-to-helical chirality conversion strategy. A series of aza[5]- and aza[4]helicenes bearing various substituents were easily obtained with good yields and high enantioselectivities. The diverse derivatizations and the preliminary application of the azahelicene derivative as a chiral organocatalyst demonstrated the potential of this method, and the photophysical and chiroptical properties of these azahelicenes were well studied, showing potential applications in novel organic optoelectronic materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Eugenia Marques-Lopez, Isaac G. Sonsona, Miryam Garces-Marin, M. Concepcion Gimeno, Raquel P. Herrera
Summary: In this study, the potential of phosphites as nucleophiles for the asymmetric synthesis of chiral chromene derivatives was explored. By employing asymmetric organocatalyzed phospha-Michael addition, chiral chromenylphosphonates were synthesized using a bifunctional squaramide. The optimized protocol provided good reactivity with yields of up to 95% and chiral products with an enantiomeric excess of up to 98%.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Mohammed Anif Pasha, K. Anebouselvy, Dhevalapally B. Ramachary
Summary: Lawsone, a red-orange dye found in henna leaves, is an important building block in the fields of chemistry and biology. In recent decades, the chemistry of lawsone has gained significant interest among synthetic organic chemists. This review summarizes the latest advances in the asymmetric synthesis of high-yielding, optically active molecules using lawsone and lawsone derivatives as key building blocks.
Review
Multidisciplinary Sciences
Anastasy O. Kolodiazhna, Oleg Kolodiazhnyi
Summary: This review focuses on the development of methods for catalytic asymmetric synthesis of phosphonates with chiral centers in the side chain. These methods have practical applications in synthesizing phosphonates with diverse biological activities found in natural compounds.
Review
Chemistry, Multidisciplinary
Cheng Niu, Da-Ming Du
Summary: This review highlights the recent advancements in sulfa-Michael addition-triggered cascade reactions for the stereoselective synthesis of sulfur-containing compounds. It discusses various types of reactions, including sulfa-Michael/aldol, sulfa-Michael/Henry, sulfa-Michael/Michael, sulfa-Michael/Mannich and some sulfa-Michael triggered multi-step processes. The review also introduces reaction mechanisms and derivatization experiments.
Article
Chemistry, Physical
Mariola Zielinska-Blajet, Joanna Najdek
Summary: An efficient approach to synthesizing chiral selenoureas derived from Cinchona alkaloid scaffolds was described in this study. These selenoureas were evaluated as bifunctional organocatalysts in asymmetric Michael addition reactions, with the best results achieved by those containing the 4-fluorophenyl group, showing enantioselectivities up to 96% ee. Additionally, the catalytic performance of thiourea and selenourea counterparts was compared.
Review
Chemistry, Organic
Regina Westphal, Eclair Venturini Filho, Fabrizio Medici, Maurizio Benaglia, Sandro J. Greco
Summary: This review summarizes the latest developments in asymmetric domino reactions, with a focus on the preparation of spiro compounds. Discussions on the stereoselectivity of the transformations, reaction mechanisms, rationalization of the stereochemical outcome, and the applications of domino reactions to the synthesis of biologically active molecules and natural products are included.
SYNTHESIS-STUTTGART
(2022)
Review
Chemistry, Organic
Helene Pellissier
Summary: This review discusses the major advancements in the total synthesis of bioactive products using enantioselective organocatalytic domino/tandem reactions as key steps, including those based on asymmetric Michael-initiated domino reactions and aldol-initiated domino/tandem reactions.
CURRENT ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Martina Bortolami, Francesca Leonelli, Marta Feroci, Fabrizio Vetica
Summary: Organocatalysis has been shown to be a powerful tool for the asymmetric synthesis of oxindole-based compounds, offering advantages such as step- and atom-economy, environmental friendliness, and non-toxicity.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Vojtech Docekal, Tereza Koberova, Jan Hrabovsky, Andrea Vopalenska, Robert Gyepes, Ivana Cisarova, Ramon Rios, Jan Vesely
Summary: A new asymmetric organocatalytic cascade reaction was reported for the synthesis of enantiopure chiral boron dipyrromethenes (BODIPYs), with high isolated yields and enantiomeric excesses. The method showed synthetic versatility and was successfully applied to a series of additional transformations of the corresponding optically pure compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Artur Przydacz, Aleksandra Topolska, Anna Skrzynska, Sebastian Frankowski, Lukasz Albrecht
Summary: This manuscript presents the application of amino isobenzofulvene intermediates as pentaenamines in a 1,6-addition reaction. The alkylation of the indene ring in indene-2-carbaldehydes with para-quinone methides was achieved, with the stereoselectivity controlled by C-2-symmetric 2,5-diphenylpyrrolidine. The developed process utilizes the reactivity of amino isobenzofulvene intermediates derived from indene-2-carbaldehydes in a non-cycloadditive manner.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Artur Przydacz, Aleksandra Topolska, Anna Skrzynska, Lukasz Albrecht
Summary: A dearomative formal (4+2)-cycloaddition reaction has been established using NHC-catalysis between 2-substituted 3-furaldehydes derivatives and isatins or alpha,alpha,alpha-trifluoroacetophenones. Highly reactive NHC-bound heterocyclic o-QDM intermediates derived from 3-furaldehydes play a key role in the process, leading to the formation of structurally diverse 6,7-dihydro-4H-furo[3,2-c]pyran-4-ones in moderate to high yields. The obtained (4+2)-cycloadducts also show potential in the synthesis of spirooxindole derivatives containing 6,7-dihydro-4H-furo[3,2-c]pyran scaffold.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Aleksandra Topolska, Sebastian Frankowski, Lukasz Albrecht
Summary: The application of differentiating catalysis in the [4 + 2]-cycloaddition reaction between 2-alkyl-3-formylheteroarenes and alpha,beta-unsaturated aldehydes is described in this paper. The use of the same aminocatalyst allows for independent activation of both starting materials, achieving high enantio- and diastereoselectivity through LUMO-lowering and HOMO-rising principles. The combination of dearomative dienamine activation with iminium ion chemistry further improves the outcome of the process.
Article
Chemistry, Organic
Marta Romaniszyn, Leslaw Sieron, Lukasz Albrecht
Summary: This study demonstrates the use of organocatalytic Brønsted base activation to generate 2π-components for the diastereoselective [8 + 2]-cycloaddition reaction involving 8,8-dicyanoheptafulvene. The use of dienolates leads to the formation of biologically relevant polycyclic products bearing a γ-butyrolactone structural motif, thus expanding the synthetic potential of Brønsted base activated higher-order cycloadditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Laura Carceller-Ferrer, Aleix Gonzalez del Campo, Carlos Vila, Gonzalo Blay, M. Carmen Munoz, Jose R. Pedro
Summary: A diastereo- and enantioselective organocatalyticaldol reaction was developed for the synthesis of chiral tertiary alcohols bearing a trifluoromethyl group from alkylidenepyrazolones and trifluoromethylketones. Despite moderate yields, the reaction showed excellent diastereoselectivity and moderate to good enantioselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Marek Moczulski, Angelika Artelska, Lukasz Albrecht, Anna Albrecht
Summary: The photocatalytic decarboxylative alkylation of 3-cyanochromones using triphenylphosphine and potassium iodide as photoredox-mediators has been described. This method is cost-effective and interesting, and allows for obtaining a number of biologically relevant products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Barbara Pacholczyk-Sienicka, Grzegorz Ciepielowski, Jakub Modranka, Tomasz Bartosik, Lukasz Albrecht
Summary: The targeted quantitative NMR (qNMR) approach is a powerful tool for classifying and determining the authenticity of honey samples. In this study, the chemical profiles of different types of Polish honey samples were determined using qNMR, and pattern recognition was performed using principal component analysis (PCA). The results showed that qNMR combined with chemometric analysis can be used as a supplementary tool for specifying honeys.
Article
Chemistry, Applied
Justyna Kowalska, Beata Lukasik, Sebastian Frankowski, Leslaw Sieron, Lukasz Albrecht
Summary: This paper demonstrates the application of organocatalysis in the synthesis of 2,3-dihydro-1H-pyrrolizines. The formal (3+2)-cycloaddition of alpha,beta-unsaturated aldehydes and pyrrole-based hydrazone was achieved through aminocatalytic iminium ion activation, resulting in products with high chemical yields and excellent stereocontrol. The developed method was also utilized in the first organocatalytic synthesis of the non-steroidal anti-inflammatory drug ketorolac.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Amparo Sanz-Marco, Daniel Esperilla, Marc Montesinos-Magraner, Carlos Vila, M. Carmen Munoz, Jose R. Pedro, Gonzalo Blay
Summary: A Cu(ii)/BOX complex catalyst was used for the enantioselective addition of difluorinated silyl enol ethers to acylpyridine N-oxides. The reaction produced difluorinated chiral tertiary alcohols, which are of great interest in medicinal chemistry. The reaction had good to excellent yields and high enantioselectivities. The stereochemical outcome of the reaction was explained by DFT calculations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Applied
Laura Carceller-Ferrer, Gonzalo Blay, M. Carmen Munoz, Jose R. Pedro, Carlos Vila
Summary: A diastereo- and enantioselective synthesis of spirocyclopropylpyrazolones was achieved through a Michael/alkylation cascade reaction of 4-arylidenepyrazol-5-ones with diethyl 2-bromomalonate catalyzed by (DHQ)(2)AQN. The corresponding spirocyclic compounds were obtained selectively with yields of 30-83%, diastereoselectivities ranging from 60:40 to >95:5, and enantiomeric excess of 26-93% under mild reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Jaume Rostoll-Berenguer, Gonzalo Blay, Jose R. Pedro, Carlos Vila
Summary: Financial support is acknowledged from grant PID2020-116944GB funded by MCIN/AEI/10.13039/501100011033, and by ERDF A way of making Europe and CIAICO/2021/147 funded by Conselleria d'Innovacio, Universitat, Ciencia i Societat Digital. J.R.-B. thanks the Ministerio de Ciencia, Innovacion y Universidades for a FPU predoctoral contract (FPU17/00688). C.V. thanks the RyC contract (RYC-2016-20187) funded by MCIN/AEI/10.13039/501100011033 and by European Union NextGeneration EU/PRTR. Access to NMR, MS, and X-ray facilities from the Servei Central de Suport a la Investigacio Experimental (SCSIE)-UV is also acknowledged.
Article
Chemistry, Multidisciplinary
Jaume Rostoll-Berenguer, Victor Garcia-Garcia, Gonzalo Blay, Jose R. Pedro, Carlos Vila
Summary: This study describes an organophotoredox 1,6-radical addition of 3,4-dihidroquinoxalin-2-ones to para-quinone methides catalyzed by Fukuzumi's photocatalyst under the irradiation of a HP Single LED (455 nm). The corresponding 1,1-diaryl compounds bearing a dihydroquinoxalin-2-one moiety (20 examples) were obtained with good to excellent yields under mild reaction conditions. Several experiments were carried out to propose a reaction mechanism.
ACS ORGANIC & INORGANIC AU
(2023)
Article
Chemistry, Multidisciplinary
Borja Ortin-Rubio, Jaume Rostoll-Berenguer, Carlos Vila, Davide M. Proserpio, Vincent Guillerm, Judith Juanhuix, Inhar Imaz, Daniel Maspoch
Summary: In this study, a generalized net-clipping approach is proposed for predicting the topology of metal-organic frameworks (MOFs) constructed from less-symmetric ligands. The approach generates less-symmetric nets with less-connected linkers through the deconstruction of more-symmetric and more-connected linkers in edge-transitive nets. The researchers successfully applied this approach to different types of linkers, resulting in several new derived and clipped nets. The feasibility of using net-clipping to predict clipped nets is supported by literature examples and new experimental additions, demonstrating the significance of this method in the rational design of new reticular materials.
Article
Chemistry, Organic
Ricardo Toran, Eduardo Portillo, Amparo Sanz-Marco, Carlos Vila, Gonzalo Blay
Summary: We report the enantioselective arylation of isoxazolin-5-ones using a bifunctional squaramide derived from Cinchona alkaloid as a catalyst. The reaction proceeds with high yields and excellent enantioselectivities, resulting in isoxazolin-5-ones featuring an arylated quaternary stereocenter. This study represents the first application of o-QDIs as arylating reagents in asymmetric catalysis.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Ricardo Toran, Dario Puchan, Amparo Sanz-Marco, Carlos Vila, Jose R. Pedro, Gonzalo Blay
Summary: An efficient organocatalytic asymmetric Mannich reaction between isoxazol-5(4H)-ones and isatin-derived ketimines has been developed. The reaction is catalyzed by a bifunctional squaramide/Bronsted base organocatalyst, resulting in the synthesis of chiral 3-aminooxindoles. The prepared compounds exhibit good yields and excellent enantioselectivities, and have demonstrated versatile synthetic transformations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
