Review
Chemistry, Applied
Sara Meninno, Francesca Franco, Maurizio Benaglia, Alessandra Lattanzi
Summary: Pyrazoleamides have gained attention as reactive and practical surrogates in asymmetric catalysis, particularly in a variety of metal- and organocatalytic transformations. Their relevance has extended to photoredox catalysis and challenging stereoselective bond-forming reactions in recent years.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Nobuya Tsuji, Pavel Sidorov, Chendan Zhu, Yuuya Nagata, Timur Gimadiev, Alexandre Varnek, Benjamin List
Summary: Catalyst optimization processes often rely on qualitative assumptions of chemists based on screening data, while machine learning models using molecular properties or calculated 3D structures are time-consuming and costly. This study proposes a machine learning model based on fragment descriptors, which are fine-tuned for asymmetric catalysis and result in robust and efficient virtual screening. Through theoretical design and experimental validation, new catalysts with higher selectivities in a challenging synthesis were developed using only moderately selective training data.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Gorka Garay, Josebe Hurtado, Manuel Pedron, Lorena Garcia, Efraim Reyes, Eduardo Sanchez-Diez, Tomas Tejero, Luisa Carrillo, Pedro Merino, Jose L. Vicario
Summary: We have demonstrated the catalytic and enantioselective rearrangement of vinylcyclopropane-cyclopentene, using (vinylcyclopropyl)acetaldehydes as starting materials and enamine intermediates for activation. The reaction involves the generation of a donor-acceptor cyclopropane, leading to the formation of an acyclic iminium ion/dienolate intermediate where stereochemistry is erased. The final cyclization step results in the stereocontrolled formation of various structurally distinct cyclopentenes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Donglei Wang, Ying-Bo Shao, Yunrong Chen, Xiao-Song Xue, Xiaoyu Yang
Summary: An efficient method for the asymmetric synthesis of planar-chiral macrocycles (paracyclophanes) has been developed using chiral phosphoric acid catalysis for enantioselective electrophilic aromatic aminations with azodicarboxylates. This method allows for the synthesis of a wide range of chiral macrocycles with varying ring sizes and functional groups, achieving high yields and enantioselectivities. The mechanism and origins of the stereoselectivities of these reactions were investigated through experimental studies and computational calculations. Preliminary utilization of the planar-chiral macrocycle as a chiral organocatalyst demonstrated the potential applications of these novel chiral skeletons.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Esteban Matador, Javier Iglesias-Siguenza, David Monge, Pedro Merino, Rosario Fernandez, Jose M. Lassaletta
Summary: A highly enantio- and diastereoselective thiourea-catalyzed dearomatization of isoquinolines has been developed using N-tert-butylhydrazones as key neutral reagents, leading to the formation of appealing dihydroisoquinoline derivatives with excellent stereocontrol. Experimental and computational data support the generation of highly ordered complexes that play a crucial role in the selective and high-yielding transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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)
Review
Chemistry, Physical
Nilanjana Majumdar
Summary: Catalytic asymmetric transformation is a powerful strategy for synthesizing diverse nonracemic molecular entities. Carboxylic acids have been explored as building blocks in this area, and significant advancements have been made in the last three decades. They can act as both C- and O-nucleophiles, as well as electrophiles, in asymmetric reactions under catalytic conditions.
Article
Chemistry, Physical
Nilanjana Majumdar
Summary: Catalytic asymmetric transformation is a powerful strategy for introducing chirality, and the role of carboxylic acids as building blocks in catalytic asymmetric reactions is an emerging area, making them highly intriguing substrates in asymmetric catalysis research.
Review
Chemistry, Applied
Seoung-Mi Choi, Ju Hyun Kim
Summary: This review summarizes the progress made in the synthesis of 2H-pyrroles since 2000, including methods such as dearomatization of 1H-pyrrole, oxidation of pyrrolines or pyrrolidines, ring construction via catalytic cycloaddition, and rearrangement of 3H-pyrroles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Claire Segovia, Jeremy Godemert, Jean-Francois Briere, Vincent Levacher, Sylvain Oudeyer
Summary: An organocatalyzed one-pot sequential deracemization of aromatic ketones with a stereogenic center at the alpha-position was achieved through an acid-base strategy, in which enantioselective protonation reaction played a key role. This protocol provides enantioenriched ketones with up to 89% ee without isolating sensitive intermediates like silyl enolates. Water was found to be crucial in this process. This one-pot sequence serves as a valuable extension to previously reported chemically driven red-ox protocols, expanding the range of molecules eligible for deracemization.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Raquel Hidalgo-Leon, Nerea Alberro, Fernando P. Cossio, Jose Miguel Sansano, Maria de Gracia Retamosa
Summary: The highly enantioselective organocatalytic synthesis of spirocyclic compounds by Diels-Alder reactions using cyclic 2,5-dienones as precursors and different nitroalkenes as dienophiles is described. Cinchonidine-based primary amine catalyst and benzoic acid co-catalyst enable the construction of spiro compounds containing three stereogenic centres with good yields and excellent diastereo- and enantioselectivities. Computational methods have been used to investigate the plausible reaction mechanism.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Emilien Le Saux, Dengke Ma, Pablo Bonilla, Catherine M. Holden, Danilo Lustosa, Paolo Melchiorre
Summary: A general iminium ion-based catalytic method for enantioselective conjugate addition of carbon-centered radicals to aliphatic and aromatic enals is reported in this study. The process uses an organic photoredox catalyst and a chiral amine catalyst to achieve consistently high levels of stereoselectivity. This catalytic platform is demonstrated to have broad applicability in intercepting various radicals, including non-stabilized primary ones that are typically challenging to engage in asymmetric processes. Additionally, the system can be used to develop organocatalytic cascade reactions, producing stereochemically dense chiral products in one step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Seunghwan Byun, Meemie U. Hwang, Henry R. Wise, Anna V. Bay, Paul H. -Y. Cheong, Karl A. Scheidt
Summary: This study explores the enantioselective carbene-catalyzed radical-radical coupling reaction of acyl imidazoles and racemic Hantzsch esters, leading to the synthesis of chiral alpha-aryl aliphatic ketones. The method shows potential application in pharmaceutical synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Bo-Bo Gou, Yue Tang, Yan-Hong Lin, Le Yu, Qing-Song Jian, Huai-Ri Sun, Jie Chen, Ling Zhou
Summary: A new type of chiral all-carbon tetrasubstituted VQMs was successfully prepared via nucleophilic addition of 2-alkynylnaphthols to o-quinone methides or imines, catalyzed by chiral phosphoric acids. The method showed high efficiency and excellent diastereoselectivities and enantioselectivities, leading to the synthesis of naphthyl-2H-chromenes with axially and centrally chiral elements and axially chiral quinone-naphthols. The obtained axially chiral naphthols could further be converted into valuable phosphine ligands and other functional molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Chenxiao Qian, Pengfei Li, Jianwei Sun
Summary: A catalytic enantioselective variant of oxidative rearrangement of indoles to access oxindoles has been developed using chiral phosphoric acid catalysis, providing a rapid access to a range of enantioenriched spirooxindoles with high enantioselectivity controlled by dynamic kinetic resolution.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Inorganic & Nuclear
Juan Carlos Perez-Sanchez, Raquel P. Herrera, M. Concepcion Gimeno
Summary: This review explores the recent advancements in the combination of the ferrocene structure with gold-mediated catalysis in the field of organometallic chemistry, discussing the application and potential of ferrocene in gold catalysis.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Isaac G. Sonsona, Andrea Vicenzi, Marco Guidotti, Giorgiana Denisa Bisag, Mariafrancesca Fochi, Raquel P. Herrera, Luca Bernardi
Summary: The study demonstrates the improved selectivity of an asymmetric aldol reaction by replacing part of the catalyst, and identifies the most suitable reaction conditions. However, these conditions seem to be limited to oxindoles bearing a 3-substituent of funapide.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Aliasghar Jarrahpour, Zahra Jowkar, Zahra Haghighijoo, Roghayeh Heiran, Javad Ameri Rad, Veronique Sinou, Florent Rouvier, Christine Latour, Jean Michel Brunel, Namik Ozdemir
Summary: A class of novel spiro-beta-lactam isatin hybrids were synthesized through a [2 + 2] cycloaddition reaction and evaluated for their biological activities. The compounds showed moderate to good activities against P. falciparum K1 strain, but exhibited unsatisfactory antimicrobial activities against Gram-positive and Gram-negative bacteria.
MEDICINAL CHEMISTRY RESEARCH
(2022)
Article
Materials Science, Biomaterials
Alireza Sanei-Dehkordi, Roghayeh Heiran, Mohammad Djaefar Moemenbellah-Fard, Sina Sayah, Mahmoud Osanloo
Summary: The larvicidal effects of essential oils of Satureja khuzestanica and Zataria multiflora, as well as their components, carvacrol, were investigated in this study. The use of nanoliposomal forms yielded better results compared to non-formulated states. These findings suggest that these samples could be potential green larvicides for other mosquito populations.
Review
Biochemistry & Molecular Biology
Sandra Ardevines, Eugenia Marques-Lopez, Raquel P. Herrera
Summary: This review summarizes the research on pyrazole derivatives as antitumor agents. Pyrazole, a five-membered aromatic heterocycle ring with two adjacent nitrogen atoms, has been postulated as a potent candidate in the pharmacological context. Due to its presence in many natural substances, pyrazole is an interesting therapeutic target covering a broad spectrum of biological activities, and its potential as antitumor agents has been explored in various investigations, showing promising results in certain cases. Therefore, this review focuses on breast cancer, the leading cause of cancer mortality in women in some countries, and covers a range of research from the earliest studies published in 2003 to the most recent ones in 2021.
CURRENT MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Elham Riazimontazer, Roghayeh Heiran, Aliasghar Jarrahpour, Ahmad Gholami, Zahra Hashemi, Aboozar Kazemi
Summary: Beta-lactam antibiotics are critical antibacterial agents in modern medicine. In this study, monocyclic beta-lactams with various substituents were synthesized through the Staudinger cycloaddition reaction. The synthesized beta-lactams showed potential antibacterial activity against various strains, including multidrug-resistant pathogens. Molecular docking analysis indicated that compound 4d could serve as a promising lead compound for the treatment of infectious diseases.
Article
Chemistry, Multidisciplinary
Sandra Ardevines, Fernando Auria-Luna, Eduardo Romanos, Vanesa Fernandez-Moreira, Andrea Benedi, M. Concepcion Gimeno, Isabel Marzo, Eugenia Marques-Lopez, Raquel P. Herrera
Summary: 1,4-Dihydropyridine is a privileged scaffold with good anticancer activity. A family of 23 new compounds based on this structure core has been synthesized, and their cytotoxicity and photo-physical properties have been evaluated.
ARABIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Applied
Sandra Ardevines, Devan Horn, Juan Alegre-Requena, Marta Gonzalez-Jimenez, M. Concepcion Gimeno, Eugenia Marques-Lopez, Raquel P. Herrera
Summary: An enantioselective C-P bond formation has been developed by activating C(sp(3))-H in an oxidation step, followed by an organocatalytic hydrophosphonylation protocol. The Pudovik reaction achieved asymmetric organocatalysis using a one-pot strategy with different alcohols and phosphite, MnO2 as the oxidant, and a chiral squaramide as the organocatalyst. The reaction scope produced enantiomerically enriched a-hydroxy phosphonates with yields ranging from 40% to >95% and enantioselectivities from 64% to >99%. Furthermore, this methodology has demonstrated the formation of a tetrasubstituted carbon stereocenter in situ, using diphenyl phosphite, to generate an acetophenone derivative. Therefore, this approach represents an asymmetric strategy for constructing chiral C-P bonds, which is significant for the pharmaceutical industry.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Polymer Science
Alireza Valizadeh, Mehrnaz Hosseinzadeh, Roghayeh Heiran, Shekoufeh Hatami, Ali Hosseinipour, Mahmoud Osanloo
Summary: This study investigated the anticancer activity of Lavandula angustifolia essential oil and alginate nanoparticles containing L. angustifolia essential oil. The essential oil components were characterized using GC-MS, and the nanoparticle size was analyzed by DLS. The cytotoxicity of the essential oil and nanoparticles on melanoma and breast cancer cell lines was evaluated, and gene expression was assessed using RT-qPCR. Alginate nanoparticles containing L. angustifolia essential oil showed significant anticancer activity and affected apoptosis regulator genes, making them a potential candidate for in vivo studies.
Article
Polymer Science
Hamidreza Rahmani, Ali Ghanbariasad, Mohammad Hassan Meshkibaf, Alireza Molazade, Roghayeh Heiran, Mojdeh Safari, Mahmoud Osanloo
Summary: Melanoma is a deadly form of skin cancer, and due to the drawbacks of chemotherapeutic drugs, there is a focus on developing new herbal drugs. This study identified the chemical composition of Rosmarinus officinalis essential oil and prepared chitosan nanoparticles containing the oil along with alpha-pinene. The efficacy of the nanoparticles containing alpha-pinene was found to be more potent than other formulations, and it was confirmed that the effect on cell viability occurred through the apoptosis pathway.
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, Multidisciplinary
Stephany Zarate-Roldan, M. Concepcion Gimeno, Raquel P. Herrera
Summary: A novel approach for allylic alkylation using a variety of allylic alcohols under mild conditions and deep eutectic solvents (DESs) is described. The use of a simple DES mixture of choline chloride (ChCl) and lactic acid has shown excellent results for a wide range of substrates, providing a greener alternative to previously reported methods. This procedure also demonstrates the trapping of allylic carbocations with indole derivatives and the successful use of challenging nucleophiles such as amides, carbamates, azides, and sulfonamides.
Article
Chemistry, Inorganic & Nuclear
Daniel Salvador-Gil, Raquel P. Herrera, M. Concepcion Gimeno
Summary: The reaction between propargylamines and isothiocyanates can selectively produce iminothiazolidines, aminothiazolines, or mixed thiazolidine-thiourea compounds under mild conditions. Secondary propargylamines lead to the formation of cyclic 2-amino-2-thiazoline derivatives, while primary propargylamines form iminothiazoline species. These cyclic thiazoline derivatives can further react with excess isothiocyanate to give rise to thiazolidine-thiourea compounds. Coordination studies of these heterocyclic species towards silver and gold have been conducted, resulting in the synthesis of complexes of different stoichiometries. Preliminary studies on the cytotoxic activity of these ligands and complexes in lung cancer cells show that their coordination to metals, especially silver, significantly enhances the cytotoxic activity.
DALTON TRANSACTIONS
(2023)
Review
Chemistry, Inorganic & Nuclear
Juan Carlos Perez-Sanchez, Raquel P. Herrera, M. Concepcion Gimeno
Summary: Gold(II) complexes have been less utilized in catalysis compared to their gold(I) and gold(III) counterparts. However, gold(II) complexes offer potential in homo-coupling and cross-coupling reactions, as they are more easily accessible through simplified oxidation and reduction processes. Gold(II) exhibits characteristics of both soft acid gold(I) and hard acid gold(III). This review explores the unique reactivity and potential applications of gold(II) species, highlighting their significance in catalytic transformations.
DALTON TRANSACTIONS
(2024)
Review
Materials Science, Multidisciplinary
Abolfazl Ghaderian, Roghayeh Heiran, Samrana Kazim, Shahzada Ahmad
Summary: The development of sustainable and cost-effective energy resources is a challenging task. Utilizing solar energy and employing polymers as charge transporting layers can improve the reliability and performance of solar cells, advancing their commercial viability.
JOURNAL OF MATERIALS CHEMISTRY C
(2022)
