Article
Chemistry, Applied
Enrico Marcantonio, Claudio Curti, Lucia Battistini, Andrea Sartori, Luana Cardinale, Giorgio Pelosi, Franca Zanardi
Summary: The remote enolization strategy, strategic exploitation of noncovalent bifunctional organocatalysis, and efficient stereoselective trapping of dienolate intermediates with nitroolefins led to the successful synthesis of functionalized, chiral carbocycle-fused uracils with three contiguous stereocenters in one step, showing good levels of enantioselectivity and complete diastereocontrol. Furthermore, the enantiopure products could be obtained via simple one-cycle recrystallizations and the scaffolds could be further functionalized without losing their chiral integrity.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Vinod Bhajammanavar, Popuri Sureshbabu, Mallu Kesava Reddy, Mahiuddin Baidya
Summary: The cascade annulation between alkylidene malononitriles and cyclic sulfamidate imines was controlled under organocatalysis, allowing selective access to polycyclic and densely functionalized dihydropyridines and pyridines in high yields. The protocol is scalable and has a broad substrate scope, and the products were further utilized in the synthesis of tetracyclic pyridopyrimidines, demonstrating synthetic versatility.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Applied
Tao Wang, Bo Huang, You-Qing Wang
Summary: Using chiral phosphoric acids as organocatalysts, a formal asymmetric (4+2) cycloaddition of 3-methylene isoindolinone and in situ-generated ortho-quinone methide substrates is achieved. This reaction allows the construction of spiro chroman-isoindolinones containing spiro-N,O-heterocycles with high enantioselectivity, with a broad substrate scope.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Enrico Marcantonio, Debora Guazzetti, Kelly Bugatti, Lucia Battistini, Andrea Sartori, Giorgio Pelosi, Claudio Curti, Franca Zanardi
Summary: Organocatalytic asymmetric transformation of aromatic heterocycles via in situ formation of reactive diene species and subsequent cycloaddition has become a powerful tool. This study reveals the efficient and direct preparation of 6,7-dihydrobenzo[d]imidazoles with optimal enantio- and regioselectivities using previously intractable aromatic imidazole rings as cycloaddends. Post-cycloaddition chemical editing allows the modification of imidazole-based ring systems.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Organic
Anup Biswas, Avisek Ghosh, Rajat Shankhdhar, Indranil Chatterjee
Summary: Chiral analogues of squaramides have proved to be efficient asymmetric catalysts in the synthesis of acyclic and cyclic chiral molecules. By utilizing several bifunctional squaramides as catalysts, a wide range of cyclic molecules bearing multiple functionalities and stereocenters have been successfully synthesized.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Nicolaj Inunnguaq Jessen, Maksimilian Bura, Giulio Bertuzzi, Karl Anker Jorgensen
Summary: An efficient and stereoselective synthesis of chiral cycl[3.2.2]azines has been achieved through the rational design and utilization of novel (E)-3-benzylidene-3H-pyrrolizines in iminium-ion catalysis. The method allows for incorporation of diverse enals and the obtained products can undergo selective transformations while retaining stereochemical information established in the [8+2] cycloaddition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Pierre Milbeo, Arthur Lebrene, Mariia Savchuk, Giang Vo-Thanh, Sylvain Oudeyer, Helene Beucher, Jean-Francois Briere
Summary: A highly diastereoselective organocatalyzed domino vinylogous sulfa-Michael-aldol-cyclocondensation (VMAC) reaction has been developed using alkylidene Meldrum's acid as dienes, showcasing an unprecedented sulfa-1,6-conjugate addition and a diastereoselective aldol reaction leading to a formal (4+2) cycloaddition. This research provides a new approach to synthesize bio-relevant and original tricyclic thiochroman derivatives.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
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)
Article
Biochemistry & Molecular Biology
Antonia Di Mola, Felice De Piano, Lorenzo Serusi, Giovanni Pierri, Laura Palombi, Antonio Massa
Summary: The investigation of the reactivity of an alpha-amido sulfone derived from 2-formyl benzoate under organocatalytic conditions in the presence of acetylacetone allowed the synthesis of a new heterocyclic hybrid isoindolinone-pyrazole with high enantiomeric excess. Dibenzylamine was also used as a nucleophile to afford an isoindolinone with aminal substituent in 3-position in suitable selectivity. The use of Takemoto's bifunctional organocatalyst not only led to observed enantioselectivity but was also important in accomplishing the cyclization step in both cases. Notably, this catalytic system proved to be particularly effective in comparison to widely used phase transfer catalysts.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Caroline Dorsch, Christoph Schneider
Summary: We describe a catalytic asymmetric cyclization of 1-aryl terpenols to produce enantiomerically enriched Delta(9)-cis-tetrahydrocannabinoid scaffolds in a one-step process. Powerful chiral catalysts, strongly acidic imidodiphosphorimidates (IDPis), were identified to give the products in good yields and excellent enantioselectivity. After MOM-deprotection, some naturally occurring cannabimimetics such as (-)-cis-Delta(9)-tetrahydrocannabinol and (-)-perrottetinene, as well as some unnatural analogues, were accessible through a simple 3-step biomimetic sequence.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Karen R. Winters, Jean-Luc Montchamp
Summary: A series of P-stereogenic chiral phosphorus acids (CPAs) were synthesized to determine the requirements for efficient asymmetric organocatalysis. Although the efficacy of these compounds was disappointing for the specific reaction, the study is valuable for developing structural design elements.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Tibor Penaska, Vitalii Palchykov, Erik Rakovsky, Gabriela Addova, Radovan Sebesta
Summary: The stereoselective formation of spiro oxindole pyrrolidines via formal [3+2] cycloaddition of oxindole imines with ketoesters and ketoamides was investigated, with bifunctional squaramide organocatalyst inducing enantioselectivity of up to 72% ee. Ketoamides provided alternative products, and the reaction pathway was elucidated with the help of DFT calculation.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Achille Antenucci, Giovanni Ghigo, Davide Cassetta, Marco Alcibiade, Stefano Dughera
Summary: Chiral phosphoric acids (CPAs) and their salts have been widely used as privileged catalysts in asymmetric transformations. Previous efficient CPAs have relied on C-2 symmetry and axial chirality, with the only exception being TADDOL derivatives. In this study, we have designed and synthesized C-2 symmetric cycloglycerophosphates (cGPAs), which were applied in the addition of trimethylsilyl cyanide (TMSCN) to aldehydes and ketones. The corresponding cyanohydrins were obtained with yields between 77% and 99% and enantiomeric excesses between 84.2% and 99.5%, in 27 examples. A DFT computational model was also used to rationalize the reaction mechanism and stereochemical outcome.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Jia-Hong Wu, Jian-Ping Tan, Jia-Yan Zheng, Jiajia He, Zhenlei Song, Zhishan Su, Tianli Wang
Summary: In this article, a general and modular protocol for the synthesis of axially chiral arylpyrazole scaffolds containing a phosphorus unit is described. The reaction is catalyzed by a dipeptide phosphonium salt and involves an oxidative central-to-axial chirality conversion. The reaction demonstrates excellent yields and enantioselectivities, a broad substrate scope, and a low catalyst loading, leading to the formation of axially chiral phosphine compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Taiki Morita, Hiroki Murakami, Yasunobu Asawa, Hiroyuki Nakamura
Summary: In this study, a palladium-catalyzed N-H/B-H double activation of 1,2-dihydro-1,2-benzazaborines proceeded via cycloaddition with vinyl ethylene carbonate to produce polycyclic oxazaborolidines in moderate to high yields. Chiral oxazaborolidines were synthesized using a SPINOL-derived phosphoramidite as a chiral ligand, showing excellent enantioselectivity. The resulting oxazaborolidines demonstrated good stability in various carbon-carbon coupling reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Claudio Curti, Lucia Battistini, Andrea Sartori, Franca Zanardi
Article
Chemistry, Multidisciplinary
Claudio Curti, Gloria Rassu, Marco Lombardo, Vincenzo Zambrano, Luigi Pinna, Lucia Battistini, Andrea Sartori, Giorgio Pelosi, Franca Zanardi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Kelly Bugatti, Agostino Bruno, Daniela Arosio, Andrea Sartori, Claudio Curti, Lisa Augustijn, Franca Zanardi, Lucia Battistini
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Applied
Enrico Marcantonio, Claudio Curti, Lucia Battistini, Andrea Sartori, Luana Cardinale, Giorgio Pelosi, Franca Zanardi
Summary: The remote enolization strategy, strategic exploitation of noncovalent bifunctional organocatalysis, and efficient stereoselective trapping of dienolate intermediates with nitroolefins led to the successful synthesis of functionalized, chiral carbocycle-fused uracils with three contiguous stereocenters in one step, showing good levels of enantioselectivity and complete diastereocontrol. Furthermore, the enantiopure products could be obtained via simple one-cycle recrystallizations and the scaffolds could be further functionalized without losing their chiral integrity.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Organic
Lucia Battistini, Kelly Bugatti, Andrea Sartori, Claudio Curti, Franca Zanardi
Summary: Targeted therapies have gained increasing interest in recent years as effective strategies to improve therapeutic efficiency, especially in the field of cancer chemotherapeutics. RGD peptide-drug conjugates offer new possibilities for targeted drug delivery systems.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Nutrition & Dietetics
Pedro Mena, Claudia Favari, Animesh Acharjee, Saisakul Chernbumroong, Letizia Bresciani, Claudio Curti, Furio Brighenti, Christian Heiss, Ana Rodriguez-Mateos, Daniele Del Rio
Summary: This study aims to investigate the inter-individual variability in the metabolism of flavan-3-ol metabolites, defining different metabotypes through various data pre-treatment and clustering methods. The validation and robustness of urinary metabotypes in flavan-3-ol metabolism were confirmed, providing a step towards understanding the individual differences in this metabolism.
EUROPEAN JOURNAL OF NUTRITION
(2022)
Article
Chemistry, Multidisciplinary
Ignjat P. Filipovic, Emina M. Mrkalic, Giorgio Pelosi, Vesna Kojic, Dimitar Jakimov, Dejan Baskic, Zoran D. Matovic
Summary: A new dicarboxylato-diamide-type compound was synthesized and characterized. It showed reasonable dose-dependent cytotoxicity against cancer cells and selectivity towards normal cells.
JOURNAL OF THE SERBIAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Kelly Bugatti, Elena Andreucci, Noemi Monaco, Lucia Battistini, Silvia Peppicelli, Jessica Ruzzolini, Claudio Curti, Franca Zanardi, Francesca Bianchini, Andrea Sartori
Summary: This study reports the synthesis and in vitro biological evaluation of three new covalent conjugates, consisting of an alpha(V)beta(6) integrin-recognizing small cyclopeptide and nintedanib, for the treatment of fibrotic diseases. One of these conjugates demonstrates optimal antifibrotic properties in vitro. The integrin ligand within the conjugate plays a role in inhibiting fibrotic stimuli and enhancing the effect of nintedanib, while selectively targeting cells overexpressing alpha(V)beta(6) integrin.
Article
Chemistry, Organic
Kelly Bugatti, Andrea Sartori, Lucia Battistini, Jessica Ruzzolini, Chiara Nediani, Claudio Curti, Francesca Bianchini, Franca Zanardi
Summary: Melanoma, the deadliest form of skin cancer, is increasing in incidence. New studies have shown the potential of combining nintedanib with immuno- and/or targeted therapy drugs in melanoma treatment.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Enrico Marcantonio, Franca Zanardi, Claudio Curti, Marco Lombardo
Summary: In this study, the mechanism of the stereoselective (4+2) cycloaddition of N-protected 6-methyluracil-5-carbaldehydes and (E)-beta-nitrostyrenes catalyzed by Takemoto's tertiary amine/thiourea organocatalyst was explored using density functional theory calculations. The study revealed a four-step sequence involving a stereo-defining Michael addition followed by a diastereoselective intramolecular Henry reaction. Additionally, a complex network of hydrogen bonding interactions between the chiral catalyst and the reaction partners was discovered.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Enrico Marcantonio, Debora Guazzetti, Kelly Bugatti, Lucia Battistini, Andrea Sartori, Giorgio Pelosi, Claudio Curti, Franca Zanardi
Summary: Organocatalytic asymmetric transformation of aromatic heterocycles via in situ formation of reactive diene species and subsequent cycloaddition has become a powerful tool. This study reveals the efficient and direct preparation of 6,7-dihydrobenzo[d]imidazoles with optimal enantio- and regioselectivities using previously intractable aromatic imidazole rings as cycloaddends. Post-cycloaddition chemical editing allows the modification of imidazole-based ring systems.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Mirco Scaccaglia, Martina Rega, Marianna Vescovi, Silvana Pinelli, Matteo Tegoni, Cristina Bacci, Giorgio Pelosi, Franco Bisceglie
Summary: Many bacterial strains are developing resistance mechanisms to antibiotics, necessitating the search for new drugs. This study investigates the antimicrobial activity of gallium(III) complexes, which are found to be effective against antibiotic-resistant strains of Klebsiella pneumoniae, Escherichia coli, and Pseudomonas aeruginosa, without causing cytotoxicity in eukaryotic cells.
