Article
Chemistry, Organic
David A. Gutierrez, James Fettinger, K. N. Houk, Kaori Ando, Jared T. Shaw
Summary: This study describes the Lewis-acid-promoted addition of prochiral E- and Z-allyl nucleophiles to chiral alpha-alkoxy N-tosyl imines with stereochemical control, resulting in the synthesis of two isomers of clausenamide.
Article
Chemistry, Organic
Erick Martinez-Toto, Mario Ordonez, Juan C. Morales-Solis, Marcos Flores-Alamo
Summary: The diastereoselective synthesis of (2S,5R)-5-methyl-5-(phosphono)-proline, a phosphoproline derivative from L-pyroglutamic acid, is reported. The key feature of this method is the use of chiral cyclic imines as intermediates and the selective nucleophilic addition of phosphites. The target compound is obtained through cleavage and hydrolysis reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kenji Caprice, David Pal, Celine Besnard, Bartomeu Galmes, Antonio Frontera, Fabien B. L. Cougnon
Summary: This study demonstrates the amplification of a mechanically chiral (P)-catenane by binding to (R)-1,1'-binaphthyl 2,2'-disulfonate, with a diastereomeric excess of 85%. The chirality of the [2]catenane was confirmed by single crystal X-ray diffraction and NMR/CD spectroscopies, establishing a basis for the development of new synthetic approaches to enantioenriched mechanically chiral [2]catenanes.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Arun K. Ghosh, Amartyo J. Basu, Che-Sheng Hsu, Monika Yadav
Summary: The asymmetric 1,2-carbamoyl rearrangement reaction investigated in this study shows potential applications in obtaining α-hydroxy amide derivatives with excellent diastereoselectivity and high yield.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Multidisciplinary Sciences
Jiapian Huang, Fei Liu, Ling-Hui Zeng, Shaoyu Li, Zhiyuan Chen, Jie Wu
Summary: The photoredox-catalyzed sulfur dioxide insertion strategy allows for the synthesis of chiral sulfones under mild conditions. This method shows broad application potential and excellent stereospecificity. The introduction of a quaternary carbon stereocenter to derived sulfones further demonstrates the practicality and potential of this methodology.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Izabela Weglarz, Karol Michalak, Jacek Mlynarski
Summary: The study reported the first successful enantioselective hydrosilylation of cyclic imines promoted by a chiral zinc complex, achieving pharmaceutically relevant enantioenriched 2-aryl-substituted pyrrolidines with excellent enantioselectivities. The synthetic utility of the presented methodology was demonstrated in an efficient synthesis of pharmaceutical drug precursors to Aticaprant and Larotrectinib.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Yasushi Yoshida, Reina Kasuya, Takashi Mino, Masami Sakamoto
Summary: The first phase-transfer catalyzed asymmetric synthesis of alpha-chiral tetrasubstituted alpha-aminothioesters has been reported in this study, affording products with up to 81% ee. This work fills a gap in the limited existing literature on the asymmetric synthesis of these important scaffolds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Angelica Mejia Fajardo, Nicolas Queyriaux, Aurele Camy, Laure Vendier, Mary Grellier, Iker Del Rosal, Laurent Maron, Sebastien Bontemps
Summary: This study demonstrates the successful activation of the carbonyl function of five different benzaldehyde derivatives using a masked form of OBB intermediate, and the characterization and analysis of the resulting compounds through various experimental methods.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Cheng Sheng, Zheng Ling, Junzhe Xiao, Kai Yang, Xie Fang, Shengming Ma, Wanbin Zhang
Summary: In this study, enantio- and diastereoselective α-additions of 1-alkynyl ketimines with dual-copper-catalysis were successfully achieved under mild conditions, leading to the synthesis of chiral tetrasubstituted α-amino allenoates bearing a vicinal all-carbon quaternary stereocenter in high yields (up to 99% yield) with excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to >20:1 dr). The stereodivergent synthesis of the products was realized by the asymmetric α-addition reaction and the Grignard reagent promoted epimerization. Importantly, the reaction could be smoothly scaled up and applied to introduce chiral tetrasubstituted allenyl moieties into bioactive molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Shibo Yu, Qihang Cai, Tianxu Yu, Jiahui Li, Chao Yao, Yue-Ming Li
Summary: This paper describes the design and application of new chiral ligands based on binaphthyl and proline skeletons, which incorporate regulatable electronic and steric properties for the imidazoline functional groups. These ligands form chiral complexes with different metal salts and can be used as catalysts for enantioselective conjugate addition reactions, resulting in high yields and excellent enantiomeric excess.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Arne Heusler, Julian Fliege, Tobias Wagener, Frank Glorius
Summary: A novel method for the synthesis of a broad variety of N-substituted 1,4- and 1,2-dihydropyridines using amine borane as a mild and selective reducing agent is reported, expanding the scope of dearomatization strategies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Pierre Plouard, Ulysse Elmerich, Mina Hariri, Severine Loiseau, Ludovic Clarion, Jean Luc Pirat, Pierre-Georges Echeverria, Tahar Ayad, David Virieux
Summary: Asymmetric transfer hydrogenation (ATH) is a powerful method for synthesizing chiral compounds, but the reduction of alpha-ketophosphonates has been less explored. This study reports an efficient Ru-catalyzed ATH method for a broad range of alpha-ketophosphonates, offering mild conditions, operational simplicity, limited waste generation, broad substrate scope, good to excellent yields, and excellent levels of stereoinduction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Yusuke Yoshigoe, Keiichiro Hashizume, Shinichi Saito
Summary: Chiral aza-boraspirobifluorenes were synthesized and their structural and photophysical properties were evaluated. Enantiomers were separated by chiral HPLC and the absolute stereochemistry was determined. The racemization rate-determining step was found to involve the cleavage of the B-N bond.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Anna Lo, David A. Gutierrez, Garrett Toth-Williams, James C. Fettinger, Jared T. Shaw
Summary: Lewis acid mediated allylations of beta-alkoxy N-tosyl imines using allyltrimethylsilane led to the formation of anti-selective 3-alkoxy homoallylic N-tosyl amines. Two methods of Cu(OTf)(2)-mediated allylations were reported, showing that diastereoselectivity can be achieved through the 1,3 acyclic stereocontrol of beta-chiral aldimines. The observed selectivity trends and computational evidence suggest that selectivity arises through the formation of a six-membered ring chelate.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kristina Plevova, Peter Kisszekelyi, Denisa Vargova, Samuel Andrejcak, Viktor Toth, LukaS Fertal, Erik Rakovsky, Juraj Filo, Radovan Sebesta
Summary: This study demonstrates the diastereoselective double C-H heteroarylation of chiral ferrocenes using Pd-complexes with chiral mono-protected amino acids, resulting in a variety of functionalized compounds. The absolute configurations of CH-activation products were confirmed using X-ray crystallographic analysis and CD spectroscopy, while insights into the reaction mechanism and stereoinduction were provided by F-19 NMR kinetic study and DFT calculations.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Joanna Kwiczak-Yigitbasi, Jean-Luc Pirat, David Virieux, Jean-Noel Volle, Agnieszka Janiak, Marcin Hoffmann, Donata Pluskota-Karwatka
ARABIAN JOURNAL OF CHEMISTRY
(2020)
Article
Chemistry, Organic
Rachida Babouri, Lancine Traore, Yves-Alain Bekro, Victoria I. Matveeya, Yulia M. Sadykova, Julia K. Voronina, Alexander R. Burilov, Tahar Ayad, Jean-Noel Volle, David Virieux, Jean-Luc Piratt
Review
Chemistry, Organic
Tahar Ayad, Aurelie Gernet, Jean-Luc Pirat, David Virieux
Article
Chemistry, Organic
Mina Hariri, Fatemeh Darvish, Karen-Pacelye Mengue Me Ndong, Nora Sechet, Geraud Chacktas, Hooriye Boosaliki, Minh Loan Tran Do, Gabin Mwande-Maguene, Jacques Lebibi, Alexander R. Burilov, Tahar Ayad, David Virieux, Jean-Luc Pirat
Summary: This study presents a straightforward synthesis of phosphorus-based heterocycles, 2-phenyl 1H-isophosphinoline 2-oxides 1, using a gold(I) catalyzed reaction with electron-poor alkynes. The reaction, conducted under microwave activation with PPh3AuCl precatalyst and triflic acid, resulted in moderate to quantitative yields of isophosphinoline 2-oxides 1 through a regioselective 6-endo-dig hydroarylation cyclization, demonstrating a promising approach for the synthesis of phosphorus heterocycles.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
David Virieux, Francesco Delogu, Andrea Porcheddu, Felipe Garcia, Evelina Colacino
Summary: Molecular rearrangements using mechanochemistry are a powerful tool to construct complex structures in a sustainable manner, particularly for preparing active pharmaceutical ingredients and natural products. This approach, although still in its early stages, holds promise for chemists to merge molecular diversity and green chemistry perspectives towards more selective and efficient syntheses.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Lucas Mele, Jean Luc Pirat, Tahar Ayad, David Virieux
Summary: This comprehensive review summarizes the significant progress made in the synthesis of alkynylphosphorus compounds over the past 20 years. It focuses on sustainable catalysis or direct metal-free couplings from stable precursors. The review provides detailed insights into recent advancements and mechanisms of metal-catalyzed reactions, photocatalytic reactions, and metal-free reactions.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Kmar Abaid, William Erb, David Virieux, Laurent Picot, Benjamin Musnier, Valerie Thiery, Thierry Roisnel, Florence Mongin, Soufiane Touil
Summary: An efficient and simple method was developed for the synthesis of unprecedented 4,5-diphosphonyldihydropyridazines and 3,4-diphosphonylpyrroles. The reactions proceeded under operationally simple, mild, and catalyst-free conditions, and showed promising growth inhibition against melanoma cancer cells.
Article
Chemistry, Multidisciplinary
Aija Trimdale-Deksne, Artis Kons, Liana Orola, Anatoly Mishnev, Dmitrijs Stepanovs, Liliana Mazur, Magdalena Skiba, Marta K. Dudek, Nicolas Fantozzi, David Virieux, Evelina Colacino, Agris Berzins
Summary: This study investigates the factors contributing to the formation of polymorphs, hydrates, solvates, and solvate hydrates in three hydantoin-based active pharmaceutical ingredients-nitrofurantoin, furazidin, and dantrolene. Crystallographic and computational analysis of the crystal structures of these compounds reveals differences in their hydrogen bonding patterns and packing features, which correlate with their propensity to form solvates and solvate hydrates. The stability of the hydrate phases also plays a role in the differences observed.
CRYSTAL GROWTH & DESIGN
(2023)
Article
Chemistry, Multidisciplinary
Lucas Mele, Rachida Babouri, Jean-Luc Pirat, Eder Tomas-Mendivil, David Martin, Tahar Ayad, David Virieux
Summary: In the past 30 years, researchers have shown great interest in synthesizing atropochiral biaryls with steric congestion on the ortho-substituted arenes. This study presents an efficient approach to produce a new class of 2,2' disubstituted biaryls bridgehead phosphine oxides with exceptional conformational stability. The researchers found that by replacing only one hydrogen atom at the ortho position with a fluorine atom, the rotation of the biaryl backbone can be restricted at temperatures below 80°C, significantly extending the limits of atropostability. Additionally, their investigations revealed unique insights into the isomerization mechanism of these molecules.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Multidisciplinary
Nicolas Fantozzi, Jean-Noel Volle, Andrea Porcheddu, David Virieux, Felipe Garcia, Evelina Colacino
Summary: This article highlights the significance of green chemistry methods for promoting sustainable development, with a focus on batch and continuous mechanochemical methods in organic synthesis. The environmentally-friendly aspects of these methods are objectively assessed using green metrics and indicators, providing a comprehensive evaluation of their greenness. The article also provides an introduction to the topic, discusses variables influencing reaction outcomes, and offers an outlook for future research in this field.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Multidisciplinary
Lucas Mele, Raphael El Bekri Saudain, Jean-Luc Pirat, David Virieux, Tahar Ayad
Summary: A simple and rapid microwave-assisted protocol for the selective alkaline hydrolysis of phosphonate diesters has been developed, allowing efficient access to a wide variety of diversely substituted phosphonic acid monoesters. Conventional approaches struggle to obtain such compounds.
Article
Chemistry, Inorganic & Nuclear
Andrea Deak, Csaba Jobbagy, Attila Demeter, Ladislav Celko, Jaroslav Cihlar, Pal T. Szabo, Peter Abranyi-Balogh, Deborah E. Crawford, David Virieux, Evelina Colacino
Summary: A mechanochemical method was used to synthesize Au(diphos)X complexes with different luminescent colors, which can undergo reversible color changes under mechanical stimulus or solvent vapor influence. These results demonstrate the efficient and environmentally friendly synthesis of luminescent gold(I) complexes using mechanochemistry.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Organic
Aurelie Gernet, Nicolas Sevrain, Jean-Noel Volle, Tahar Ayad, Jean-Luc Pirat, David Virieux
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Aurelie Gernet, Virginie Ratovelomanana-Vidal, Jean-Luc Pirat, David Virieux, Tahar Ayad
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Joanna Kwiczak-Yigitbasi, Jean-Luc Pirat, David Virieux, Jean-Noel Volle, Agnieszka Janiak, Marcin Hoffmann, Jakub Mrzyglod, Dariusz Wawrzyniak, Jan Barciszewski, Donata Pluskota-Karwatka