Article
Chemistry, Multidisciplinary
Niklas F. Both, Anke Spannenberg, Haijun Jiao, Kathrin Junge, Matthias Beller
Summary: The use of bis(NHC) manganese(I) complexes 3 as catalysts for the hydrogenation of esters was investigated. Various aromatic and aliphatic esters were successfully hydrogenated at mild temperatures and low catalyst loadings using complexes 3 with KHBEt3 as additive, highlighting the efficiency of the novel catalytic system. Additionally, the versatility of the developed catalytic system was demonstrated by the hydrogenation of other substrate classes like ketones, nitriles, N-heteroarenes, and alkenes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yulong Zhang, Peichao Zhao, Shengnan Sun, Qian Wu, Enxue Shi, Junhua Xiao
Summary: The authors developed a camphor-derived 2,3-diol as a chiral template to synthesize diverse P(III) and P(V) chiral compounds, which are highly desirable for asymmetric catalysis in organic chemistry.
COMMUNICATIONS CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Juana M. Perez, Roxana Postolache, Marta Castineira Reis, Esther G. Sinnema, Denisa Vargova, Folkert de Vries, Edwin Otten, Luo Ge, Syuzanna R. Harutyunyan
Summary: Chiral Mn(I) complexes have been shown to activate H-P bonds, providing a general method for the hydrophosphination of internal and terminal alpha,beta-unsaturated nitriles. Metal-ligand cooperation, a previously unconsidered strategy for catalytic H-P bond activation, plays a key role in the mechanistic action of the Mn(I)-based catalyst. Computational studies support a stepwise mechanism for the hydrophosphination reaction and offer insights into the origin of enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Tanuja Tewari, Rohit Kumar, Amol C. Chandanshive, Samir H. Chikkali
Summary: Metal-catalyzed hydroformylation and hydrogenation heavily rely on ligands, with phosphorus ligands playing a pivotal role. This account presents three distinct classes of phosphorus ligands, their synthesis, performance in reactions, and the latest developments in iron-catalyzed hydroformylation of alkenes. The use of phosphines enabled iron-catalyzed hydroformylation under mild conditions, demonstrating the central role of phosphorus ligands in industrially relevant transformations.
Review
Chemistry, Inorganic & Nuclear
Jessica Margalef, Maria Biosca, Pol de la Cruz Sanchez, Jorge Faiges, Oscar Pamies, Montserrat Dieguez
Summary: The success of phosphine-oxazoline ligands has led to advancements in P-oxazoline ligand families, resulting in diverse structures and more efficient ligands for asymmetric transformations. Through proper design, these heterodonor bidentate ligand families exhibit superior catalytic performance in a variety of asymmetric reactions.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Organic
Tushar Janardan Pawar, Liliette Barcelona-Cazanave, Israel Bonilla-Landa, Magdalena Escobar, J. Oscar C. Jimenez-Halla, Alma Altuzar-Molina, Patricia Romero-Arellano, Andrew J. F. Edmunds, Martin Aluja, Jose Luis Olivares-Romero
Summary: This study presents a highly efficient iridium-catalyzed asymmetric hydrogenation approach for the total synthesis of biologically active (R,L) A. ludens host marking pheromone (HMP). The use of a novel Ir(i)-complex and a chiral P,N-ligand resulted in excellent enantioselectivities of up to 94% ee. The streamlined synthetic route involving seven reaction steps offers improved efficiency and shorter synthesis timelines compared to previous methods.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Pep Rojo, Antoni Riera, Xavier Verdaguer
Summary: The efficient electrophilic P-stereogenic transfer reagent BOM-tert-butylmethylphosphinite borane was used for the synthesis of bulky tertiary phosphines with high stereospecificity in a one-pot deprotection/substitution reaction. A wide range of tertiary phosphines in excellent enantiomeric excess was synthesized using this method, including a bulky P-stereogenic BisP* ligand analogue.
Article
Chemistry, Physical
Maria Biosca, Pol de la Cruz-Sanchez, Jorge Faiges, Jessica Margalef, Ernest Salomo, Antoni Riera, Xavier Verdaguer, Joan Ferre, Feliu Maseras, Maria Besora, Oscar Pamies, Montserrat Dieguez
Summary: Ir-MaxPHOX-type catalysts exhibit high catalytic performance in the hydrogenation of a wide range of nonchelating olefins with different geometries, substitution patterns, and degrees of functionalization. These air-stable and readily available catalysts have been successfully used in the asymmetric hydrogenation of di-, tri-, and tetrasubstituted olefins (ee ' s up to 9996). The combination of theoretical calculations and deuterium labeling experiments has revealed the factors responsible for the observed enantioselectivity, allowing for the rationalization of suitable substrates for these Ircatalysts.
Article
Chemistry, Organic
Xiaoxiao Xie, Sanliang Li, Qiaoyu Chen, Hao Guo, Junfeng Yang, Junliang Zhang
Summary: This article presents a novel method for the synthesis of chiral phosphorus ligands, and demonstrates their potential applications in catalytic asymmetric reactions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Anand B. Shabade, Dipesh M. Sharma, Priyam Bajpai, Rajesh G. Gonnade, Kumar Vanka, Benudhar Punji
Summary: Chemoselective hydrogenation of C=C, C=O and C=N bonds in alpha,beta-unsaturated ketones, aldehydes and imines can be achieved at room temperature using a well-defined Mn(I) catalyst and hydrogen gas. The method shows tolerance towards various sensitive functional groups and can be applied to unsaturated ketones containing indole, pyrrole, furan, thiophene, and pyridine moieties. In the reaction, the C=C bond is selectively hydrogenated, while the C=O and C=N bonds in aldehydes and imines are preferentially reduced.
Article
Chemistry, Organic
Barbara Mohar, Marko Jeran, Michel Stephan
Summary: Outfitting the 2MeBigFUS ligand with the branched/functionalized-alkoxy feature of the R-SMS-Phos design resulted in the 2RBigFUS family. Rhodium(I) complexes of these ligands exhibited enhanced activity and superior enantioselectivity in the hydrogenation of functionalized olefins, including challenging α-arylacrylic acids. The application of these catalysts to enantiomeric active pharmaceutical ingredients (APIs) and synthetic building blocks further highlighted their potential.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Mingxin Liu, Nguyen Le, Christopher Uyeda
Summary: Nickel catalysts promote nucleophilic cyclopropanation reactions using CH2Cl2 as a methylene source and Mn as a stoichiometric reductant. The substrate scope includes a broad range of alkenes bearing electron-withdrawing substituents, and enantioselective cyclopropanations have been developed using chiral PyBox ligands. Mechanistic studies suggest the intermediacy of a (PyBox)Ni=CH2 species and DFT models provide a rationale for the nucleophilic character of the nickel carbene and the sense of enantioinduction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yang-Ming Zhang, Shu-Min Guo, Qing-Xian Wang, Xiao-Jie Zheng, Jian-Hua Xie, Qi-Lin Zhou
Summary: This paper reports the design and synthesis of spirochroman-2-on-4,1'-indan-7'-ol (SCIOL) and its application for synthesizing chiral monophosphinite ligands. The synthesis process involves a tandem double Friedel-Crafts reaction/lactonization to construct the spiro framework, and the desired racemic SCIOL was obtained via 6 steps with a total yield of 44.5%. Optical SCIOL was obtained in good yields on a gram scale using an inclusion resolution with N-benzylcinchonidinium chloride. Preliminary studies showed that the corresponding chiral spiro monophosphinite ligands exhibit high catalytic activity and enantioselectivity (up to 94% ee) in the rhodium-catalyzed asymmetric hydrogenation of N-acetyl dehydroamino esters. These findings highlight the significant potential of SCIOL as a useful framework for the development of chiral spiro ligands.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Johannes Grosskopf, Thorsten Bach
Summary: Upon irradiation with a suitable chiral catalyst, racemic compounds can be converted into enantiopure compounds through a process called photochemical deracemization. This review comprehensively covers the research and current developments in this field, discussing the reactions and mechanistic details underlying the presented reaction. Photochemical deracemization offers a unique opportunity to directly obtain enantiopure compounds from racemates, and short-lived intermediates play a key role in determining the enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Inorganic & Nuclear
Daniel Martinez-Martinez, M. Leon Santiago, Ruben A. Toscano, Manuel Amezquita-Valencia
Summary: A series of pyridylimine ligands with variations of the substituent at the imine nitrogen were synthesized and coordinated to the [MoCl2O2] core. The novel complexes showed excellent catalytic activity and fine selectivity in the epoxidation reaction, with complex [MoCl2O2(L)] (L: N-(2-Pyridinylmethylene)-1-tert-butylimine) C-5 being the best catalytic precursor.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Thanh-Nghi Le, Patrick Diter, Bruce Pegot, Chloee Bournaud, Martial Toffano, Regis Guillot, Giang Vo-Thanh, Emmanuel Magnier
Article
Chemistry, Organic
Thi-Thuy-Duong Ngo, Thi-Huong Nguyen, Chloee Bournaud, Regis Guillot, Martial Toffano, Giang Vo-Thanh
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Khanh-Duy Huynh, Houssein Ibrahim, Lucie Bouchardy, Chloee Bournaud, Emilie Kolodziej, Martial Toffano, Giang Vo-Thanh
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Multidisciplinary
Samia Guezane-Lakoud, Martial Toffano, Louisa Aribi-Zouioueche
HETEROATOM CHEMISTRY
(2017)
Article
Chemistry, Organic
Anne-Laure Barthelemy, Alexis Prieto, Patrick Diter, Jerome Hannedouche, Martial Toffano, Elsa Anselmi, Emmanuel Magnier
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Lucie Bouchardy, Violeta Rodriguez-Ruiz, Chloee Bournaud, Francois-Didier Boyer, Martial Toffano, Patrick Judeinstein, Giang Vo-Thanh
Article
Chemistry, Applied
Alexis Prieto, Patrick Diter, Martial Toffano, Jerome Hannedouche, Emmanuel Magnier
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Article
Chemistry, Multidisciplinary
Samia Guezane Lakoud, Rim Aissa, Regis Guillot, Martial Toffano, Louisa Aribi-Zouioueche
Article
Chemistry, Physical
Samra Razi, Saoussen Zeror, Mounia Merabet-Khelassi, Emilie Kolodziej, Martial Toffano, Louisa Aribi-Zouioueche
Summary: This study compares two reaction approaches for the efficient enantioselective cleavage of alpha-phenyl ethyl esters, finding high efficiency in the presence of sodium carbonates and strong influence of acyl-chain length on conversion rates in micro-aqueous media. Lipase CAL-B demonstrates high enantioselectivities towards (R)-1-phenyl ethanol enantiomer in both conditions but with reactivity modulated by acyl-chain properties.
Article
Chemistry, Physical
Zhiwei Jiang, Martial Toffano, Giang Vo-Thanh, Chloee Bournaud
Summary: An efficient and flexible synthesis of a new class of chiral bifunctional NHC catalyst has been reported, which promotes highly diastereoselective trans-cyclopentannulation of enals and enones with good yields and excellent enantioselectivity. This methodology could be applied to a large variety of substrates.
Article
Chemistry, Multidisciplinary
Stephane Wittmann, Thomas Martzel, Cong Thanh Pham Truong, Martial Toffano, Sylvain Oudeyer, Regis Guillot, Chloee Bournaud, Vincent Gandon, Jean-Francois Briere, Giang Vo-Thanh
Summary: Through Bronsted base organocatalysis, ketone-derived alkylidene Meldrum's acids react with dihydro-2,3-furandione in a formal (4+2) cycloaddition reaction, yielding 3,6-dihydropyran-2-ones with up to 98% ee. This reaction can be extended to other activated ketones, making alkylidene Meldrum's acids a novel C4-synthon in the vinylogous series.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Medicinal
Rim Aissa, Samia Guezane-Lakoud, Martial Toffano, Lynda Gali, Louisa Aribi-Zouioueche
Summary: The chiral organocatalyst Fiaud's acid is effective in synthesizing bis alpha-aminophosphonates with excellent antifungal properties, particularly compounds 4a, 4b, 4e, 4h, 4k, and 4l exhibit strong fungicidal activity against Fusarium oxysporum and Botrytis cinerea. These compounds also demonstrate antioxidant and anti-tyrosinase abilities.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Biochemistry & Molecular Biology
Louisa Aribi-Zouioueche, Mounia Merabet-Khelassi, Nabila Braia, Martial Toffano
Summary: In this study, enantiomerically pure forms of several compounds were prepared through enzymatic kinetic resolution in organic media. The resulting compounds exhibited high enantiopurity and good synthesis yields.
BIOCATALYSIS AND BIOTRANSFORMATION
(2023)
Review
Chemistry, Multidisciplinary
Thi Thuy Duong Ngo, Khanh Duy Huynh, Houssein Ibrahim, Thi Huong Nguyen, Chloee Bournaud, Martial Toffano, Giang Vo-Thanh
VIETNAM JOURNAL OF CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Rim Aissa, Samia Guezane-Lakoud, Emilie Kolodziej, Martial Toffano, Louisa Aribi-Zouioueche
NEW JOURNAL OF CHEMISTRY
(2019)
