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)
Review
Chemistry, Multidisciplinary
Mo Wang, Zhenfeng Zhang, Wanbin Zhang
Summary: This article introduces the development of chiral bicyclic imidazole catalysts by our research group, including their design, synthesis, and application. By using different skeletons and substituents, a series of highly active and selective catalysts were successfully prepared and applied in asymmetric synthesis reactions. This research provides important insights and guidance for exploring new organocatalysts and related reactions.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Organic
Betty A. Kustiana, Rebecca L. Melen, Louis C. Morrill
Summary: In this study, a one-pot synthesis of styrene derivatives was reported. This method involved a novel B(C6F5)3-catalyzed E-selective isomerization of readily accessible allyl silanes, followed by Hiyama coupling of the resulting versatile alkenyl silane intermediates. The approach allowed access to a wide range of styrene derivatives, including those with Lewis basic functional groups, which could not be obtained through the previously developed B(C6F5)3-catalyzed isomerization of allyl benzenes.
Review
Multidisciplinary Sciences
Tsuneo Imamoto
Summary: Metal-catalyzed asymmetric synthesis is crucial for the production of optically active compounds. The success relies on the structure and electronic properties of chiral ligands. P-chiral phosphine ligands, synthesized using phosphine-boranes, exhibit excellent enantioselectivity and high catalytic activity.
PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES
(2021)
Article
Chemistry, Inorganic & Nuclear
Ding-Nan Shih, Ramalingam Boobalan, Yi-Hung Liu, Rong-Jie Chein, Ching-Wen Chiu
Summary: In recent years, a tricoordinate borenium ion has been studied for its applications in Lewis acid catalysis, as well as in the development of asymmetric catalysis mediated by a chiral borenium ion. Chloroborane masked borenium ions have been prepared to stabilize the electron-deficient boron atom and utilized as catalysts for enantioselective Diels-Alder cycloaddition reactions. Additionally, the stereoselectivity of the cycloaddition can be controlled and improved by the coordination of SnCl4 at the bridging chloride of the borenium ion.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jin Wang, Ming-Yue Ju, Xi-Meng Chen, Xuenian Chen
Summary: A general approach for synthesizing covalent and ionic amine borane complexes with trinitromethyl fragments has been developed through metathesis reactions. Five complexes were synthesized in good yields and high purity, with the ionic complex potentially being a promising energetic material based on its thermal decomposition behavior.
Article
Biochemistry & Molecular Biology
Yana Nikolova, Georgi M. Dobrikov, Zhanina Petkova, Pavletta Shestakova
Summary: A comparison study between squaric acid amides and chiral aminoalcohols as ligands in a model reduction reaction showed that aminoalcohols exhibited higher efficiency. Mechanistic insights on in situ formation and stability of intermediates generated from ligands and borane were obtained through H-1 DOSY and multinuclear NMR, contributing to a better understanding of the complexity prior to oxazaborolidine formation.
Article
Chemistry, Inorganic & Nuclear
Felix Mueller, Lucas Wickemeyer, Jan Schwabedissen, Martin Ertl, Beate Neumann, Hans-Georg Stammler, Uwe Monkowius, Norbert W. Mitzel
Summary: Two gold(I) dimers were synthesized using tin-gold exchange reactions, characterized by various experiments, and further investigated using computational and photophysical methods.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Multidisciplinary
Yan-Bo Li, Hu Tian, Shuai Zhang, Jun-Zhao Xiao, Liang Yin
Summary: In this study, a copper(I)-catalyzed reaction of diarylphosphines and O-benzoyl hydroxylamines was developed, leading to the synthesis of aminophosphinites and P-chiral aminophosphinites. The reaction mechanism was proposed and further transformation to P-chiral phosphines was achieved.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Claire N. Brodie, Timothy M. Boyd, Lia Sotorrios, David E. Ryan, Eimear Magee, Steven Huband, James S. Town, Guy C. Lloyd-Jones, David M. Haddleton, Stuart A. Macgregor, Andrew S. Weller
Summary: The study demonstrates the selective synthesis of N-methylpolyaminoborane using a specific air-tolerant precatalyst, revealing the reaction mechanism and key steps involved. This provides a theoretical basis for further research in this field.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Inorganic & Nuclear
Yana Radchenko, Shrouq Mujahed, Sanaa Musa, Dmitri Gelman
Summary: This study presents an efficient synthetic method for preparing optically active PC(sp3)P pincer ligands and their complexes, achieving the conversion of chromatographically resolvable diastereomers into enantiomerically pure antipodes. The research demonstrates that no racemization occurs during the complexation and metalation of the bifunctional PC(sp3)P pincer ligands.
INORGANICA CHIMICA ACTA
(2021)
Article
Chemistry, Inorganic & Nuclear
Maria L. Buil, Javier A. Cabeza, Miguel A. Esteruelas, Susana Izquierdo, Carlos J. Laglera-Gandara, Antonio Nicasio, Enrique Onate
Summary: The reaction of hexahydride OsH6(PiPr(3))(2) with a P,Ge,P-germylene-diphosphine leads to an osmium tetrahydride derivative with a Ge,P-chelate, serving as a bifunctional catalyst for formic acid dehydrogenation. The study reveals that hydrogen formation occurs exclusively on the coordination sphere of the metal center, while both the metal center and the sigma-donor Lewis acid cooperatively participate in CO2 release, which is the rate-determining step.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Abdusalom A. Suleymanov, Rosario Scopelliti, Kay Severin
Summary: Borylated triazenes were synthesized by various methods and the structure of the products depended on the size of the substituents. Bulky substituents resulted in open-chain structures, while smaller substituents led to the formation of novel BN3 heterocycles.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yanqing Fan, Jing He, Lin Liu, Guoqin Liu, Shengzhu Guo, Zhe Lian, Xiaonan Li, Weijie Guo, Xuebo Chen, Ying Wang, Hua Jiang
Summary: In this study, novel chiral carbon nanorings Sp-/Rp-[12]PCPP containing a planar chiral [2.2]PCP unit were synthesized and their chiroptical properties were investigated. It was found that Sp-/Rp-[12]PCPP could form ring-in-ring complexes with crown ether 18-Crown-6, as well as ternary complexes with 18-Crown-6 and S/R-protonated amines. The ternary complexes exhibited enhanced chiroptical signals and demonstrated a highly narcissistic chiral self-recognition for S/R-protonated chiral amines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Inorganic & Nuclear
Lidia Madalinska, Piotr Kielbasinski, Malgorzata Kwiatkowska
Summary: The method involves kinetic resolution through esterification, yielding moderate yields under suitable solvent conditions. P-BH3 analogues are transformed into 2-aminomethyl derivatives via intermediates for use in asymmetric synthesis.
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
(2022)
Article
Chemistry, Organic
Nicolas Glinsky-Olivier, Shengwen Yang, Pascal Retailleau, Vincent Gandon, Xavier Guinchard
Article
Chemistry, Multidisciplinary
Zhenhao Zhang, Vitalii Smal, Pascal Retailleau, Arnaud Voituriez, Gilles Frison, Angela Marinetti, Xavier Guinchard
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Organic
Nazarii Sabat, Feryel Soualmia, Pascal Retailleau, Alhosna Benjdia, Olivier Berteau, Xavier Guinchard
Correction
Chemistry, Organic
Nazarii Sabat, Feryel Soualmia, Pascal Retailleau, Alhosna Benjdia, Olivier Berteau, Xavier Guinchard
Article
Chemistry, Physical
Valentin Magne, Youssouf Sanogo, Charles S. Demmer, Pascal Retailleau, Angela Marinetti, Xavier Guinchard, Arnaud Voituriez
Article
Chemistry, Applied
Pierre Milcendeau, Vincent Gandon, Xavier Guinchard
Summary: Tertiary amines with a benzyl-type group undergo intramolecular addition to allenes under Au(I) catalysis. A formal 1,3-transfer of the CH2Ar group occurs during cyclization, involving two consecutive [3,3] rearrangements via a dearomatized intermediate. Protocols were developed to convert the unstable enamine products into more stable polycyclic chiral compounds in situ.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Pierre Milcendeau, Zhenhao Zhang, Nicolas Glinsky-Olivier, Elsa van Elslande, Xavier Guinchard
Summary: Au(I) complexes catalyze iso-Pictet-Spengler reactions, introducing ethylamine or methylamine chains with selectivity. This leads to the formation of highly complex molecules through double iso-Pictet-Spengler reactions involving successive aldehydes.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Nazarii Sabat, Weiping Zhou, Vincent Gandon, Xavier Guinchard, Guillaume Vincent
Summary: This study reports a method for the direct addition of arenes to the C3 position of unprotected indoles using triflic acid at room temperature. This simple and efficient method allows for the synthesis of biologically relevant 3-arylindolines and 3,3-spiroindolines in high yields.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Feryel Soualmia, Alain Guillot, Nazarii Sabat, Clemence Brewee, Xavier Kubiak, Michael Haumann, Xavier Guinchard, Alhosna Benjdia, Olivier Berteau
Summary: B-12-dependent radical SAM enzyme TsrM has been found to catalyze both C- and N-methyl transfer reactions, and has the unique ability to directly transfer a methyl group to the benzyl core of tryptophan.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Physical
Zhenhao Zhang, Nazarii Sabat, Gilles Frison, Angela Marinetti, Xavier Guinchard
Summary: This study presents a new gold(I) catalyst for highly enantioselective multicomponent reactions between aldehydes, hydroxylamines, and cyclic yne-enones. The method shows broad applicability and achieves high yields, total diastereoselectivity, and high enantiomeric excess.
Review
Chemistry, Physical
Floris Buttard, Xavier Guinchard
Summary: Spirocyclic indole derivatives, as tridimensional molecular scaffolds, have attracted much attention due to their unique reactivity and structural diversity. Transition metal catalysis has played a crucial role in the synthesis of these compounds, particularly involving the activation of functional groups tethered to indole derivatives. This review focuses on the spirocyclization reactions leading to both spirocyclic and rearomatized products, and discusses the reactive intermediates and complex mechanistic features associated with different catalytic systems.
Article
Chemistry, Organic
Yunliang Yu, Nazarii Sabat, Meriem Daghmoum, Zhenhao Zhang, Pascal Retailleau, Gilles Frison, Angela Marinetti, Xavier Guinchard
Summary: Enantioselective tandem cycloisomerization/addition reactions of 2-alkynyl enones with 1- and 2-naphthols were investigated using gold(I) catalysts featuring hybrid phosphine-phosphoric acid chiral ligands, based on the tethered counterion-directed catalysis strategy. The reactions proceeded at low catalyst loading (0.2-1 mol%) without the need for silver additives, and the naphthols acted as both O- and C-nucleophiles, resulting in the formation of addition products with high enantioselectivity. The mechanism of these reactions was elucidated by DFT calculations.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Yunliang Yu, Zhenhao Zhang, Arnaud Voituriez, Nicolas Rabasso, Gilles Frison, Angela Marinetti, Xavier Guinchard
Summary: Stereocontrol in the enantioselective Au(i) catalyzed dearomatizations of 1-naphthols with allenamides is achieved through intramolecular ion-pairing between the chiral gold-tethered phosphate and an iminium unit, providing a rigid and well-defined chiral environment for the key electrophilic intermediate.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Organic
Pierre Milcendeau, Nazarii Sabat, Angelique Ferry, Xavier Guinchard
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Organic
Valentin Magne, Pascal Retailleau, Angela Marinetti, Arnaud Voituriez, Xavier Guinchard
