Article
Chemistry, Physical
Nansalmaa Otog, Hayato Inoue, Doan Thi Thuy Trinh, Zolzaya Batgerel, Niklas Maximilian Langendorf, Ikuhide Fujisawa, Seiji Iwasa
Summary: The stereoselective synthesis of optically active cyclopropylsilanes was achieved in excellent yields and diastereo- and enantioselectivities with Ru(II)-Pheox catalysts. Among these catalysts, p-MeO-Ru(II)-Pheox was found to be the best for cyclopropanation reactions. The derivatives of cyclopropylsilanes could be transformed into beneficial building blocks for the synthesis of bioactive compounds.
Article
Chemistry, Organic
Cidan Lv, Xiangxiang Meng, Min Wang, Yan Zhang, Changwei Hu, Chan Kyung Kim, Zhishan Su
Summary: The mechanism and stereoselectivity of an asymmetric cyclopropanation reaction between 3-alkenyl-oxindole and sulfoxonium ylide catalyzed by a chiral N,N'-dioxide-Mg(II) complex were explored. The presence of N-protecting groups in the isatin enhanced the reactivity of the reactants, while steric effects of substituents in the chiral ligand played a crucial role in the selectivity of the reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Tianjiao Hu, Lukas Lueckemeier, Constantin Daniliuc, Frank Glorius
Summary: The direct enantioselective hydrogenation of 2-quinolones using Ru(II)-NHC catalyst has been achieved, providing alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones in high yields with moderate to excellent enantioselectivities. This reaction presents an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Bo Yang, Jihui Gao, Xingfa Tan, Yicong Ge, Chuan He
Summary: A new type of chiral silyl ligand is developed, enabling the first iridium-catalyzed atroposelective intermolecular C-H silylation reaction of 2-arylisoquinolines. This protocol offers mild reaction conditions, high atom economy, and remarkable yield with excellent stereoselectivity, delivering enantioenriched axially chiral silane platform molecules with facile convertibility. The success of this unprecedented transformation relies on a novel chiral PSiSi-ligand, which facilitates the intermolecular C-H silylation process with perfect chem-, regio-, and stereo-control via a multi-coordinated silyl iridium complex.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yun-Xuan Tan, Shijia Li, Lijuan Song, Xinhao Zhang, Yun-Dong Wu, Jianwei Sun
Summary: The first geminal hydroborative cyclization of enynes is disclosed in this study. Unlike known hydroborative cyclizations, this reaction adds hydrogen and boron to the same position, leading to a new reaction mode. By using a specific catalyst, a variety of gem-hydroborated bicyclic products with a cyclopropane unit can be rapidly formed from simple enyne substrates. Control experiments and calculations provide important insights into the reaction mechanism. Notably, two competing pathways may operate, depending on the substrate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Pinke Yu, Danyi Chen, Yiwen Liu, Congcong Yin, Qixing Liu, Haifeng Zhou
Summary: An asymmetric transfer hydrogenation of 2-oxazolones using a chiral diamine ruthenium catalyst, potassium formate as a hydrogen source, potassium carbonate as an additive in 2,2,2-trifluoroethanol has been described. The reaction yielded a series of chiral 2-oxazolidinones with 29%-95% yields and 86%->99% ee's. Gram-scale synthesis and downstream derivatizations of chiral 2-oxazolidinone demonstrate the practicality of this method.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Saikat Das, Azusa Kondoh, Masahiro Terada
Summary: The direct use of cyanohydrin ether derivatives as less acidic pronucleophiles was achieved for the first time in the catalytic enantioselective Michael addition reaction under transition metal free conditions. Chiral bis(guanidino)iminophosphoranes as the higher order organosuperbase facilitated the intended catalytic Michael addition to enones, giving rise to the corresponding products in high yields with moderate to high diastereo- and enantioselectivities in most cases. Further elaboration of the corresponding enantioenriched product was conducted by derivatization into a lactam derivative through hydrolysis followed by cyclo-condensation.
Article
Biochemistry & Molecular Biology
Zita Szabo, Sophia Ben Ahmed, Zoltan Nagy, Attila Paczal, Andras Kotschy
Summary: The formation of polysubstituted cyclopropane derivatives in the gold(I)-catalyzed reaction of olefins and propargylic esters is of significant interest due to its potential usefulness in generating diversity. We tested a series of chiral gold(I)-carbene complexes as catalysts and achieved high enantioselectivity in the test reaction. However, the cis:trans selectivity of the transformation was independent of the catalyst. Although the reactions proceeded smoothly, the observed enantioselectivity varied greatly and a structure-property relationship could not be established.
Article
Chemistry, Organic
Jixin Pian, Qingqing Chen, Yujiao Luo, Zhifei Zhao, Jichang Liu, Lin He, Shi-Wu Li
Summary: An enantioselective cyclopropanation reaction of sulfoxonium ylides with beta,gamma-unsaturated ketoesters catalyzed by a chiral rhodium catalyst has been achieved, leading to the synthesis of various optically pure cyclopropanes.
Article
Chemistry, Multidisciplinary
Mikus Purins, Jerome Waser
Summary: The paper explores the enantioselective diversification of a single starting material by extending the concept of catalytically formed chiral auxiliary from hydrogenation to cyclopropanation and epoxidation reactions. This approach eliminates the need for different chiral catalysts in alkene functionalization and allows for the control of stereochemistry using a catalytically constructed chiral auxiliary.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Ruxia Mao, Yanliang Zhao, Xiaohan Zhu, Fen Wang, Wei-Qiao Deng, Xingwei Li
Summary: In this study, enantioenriched allenes were successfully obtained through Rhodium(III)-catalyzed C-H allenylation of tertiary propargyl alcohols. The reaction proceeded efficiently under mild conditions, resulting in high enantioselectivities for both the allenylated products and propargyl alcohols. The resolution was achieved through bias of the propargylic substituents and assistance of a chiral zinc carboxylate additive.
Article
Chemistry, Multidisciplinary
Matthias Peeters, Jonathan Decaens, Alois Fuerstner
Summary: Chiral [BiRh]-paddlewheel complexes empowered by London dispersion enable the generation of (trifluoromethyl)furfurylidene metal complexes from a bench-stable triftosylhydrazone precursor. These complexes undergo asymmetric [2+1] cycloadditions, providing optically active trifluoromethylated cyclopropane or -cyclopropene derivatives, which are important building blocks for medicinal chemistry and difficult to obtain in optically active form.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Uttam Dhawa, Robert Connon, Joao C. A. Oliveira, Ralf Steinbock, Lutz Ackermann
Summary: The asymmetric ruthenium-catalyzed C-H alkylations were achieved using a chiral C2-symmetric carboxylic acid, resulting in chiral tetrahydrocarbazoles and cyclohepta[b]indoles with high enantioselectivity at room temperature. Mechanistic studies revealed a fast C-H ruthenation process, with a rate- and enantio-determining proto-demetalation step. The asymmetric induction was governed by weak attractive secondary dispersion interactions, as shown in NCI analysis of the key transition states.
Article
Chemistry, Multidisciplinary
Shun Sakurai, Tetsuya Inagaki, Takuya Kodama, Masahiro Yamanaka, Mamoru Tobisu
Summary: This study demonstrates that acylsilanes can serve as a source of electron-rich carbenes under palladium catalysis, enabling the cyclopropanation of alkenes. This new reactivity profile provides a valuable method for accessing elaborate beta-functionalized ketones.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Zhenzhong Li, Lorenz Roesler, Till Wissel, Hergen Breitzke, Torsten Gutmann, Gerd Buntkowsky
Summary: A novel immobilized chiral dirhodium catalyst has been prepared and shows high catalytic activity and significant enantioselectivity in asymmetric cyclopmpanation reaction. The catalyst can be readily recovered and reused.
JOURNAL OF CO2 UTILIZATION
(2021)
Article
Chemistry, Multidisciplinary
Irene Nicolas, Frederic Barriere, Olivier Jeannin, Marc Fourmigue
CRYSTAL GROWTH & DESIGN
(2016)
Article
Chemistry, Multidisciplinary
Irene Nicolas, Olivier Jeannin, Delphine Pichon, Marc Fourmigue
Article
Multidisciplinary Sciences
Min Ruan, Irene Nicolas, Michele Baudy-Floc'h
Article
Chemistry, Physical
Emmanuel Aubert, Enrique Espinosa, Irene Nicolas, Olivier Jeannin, Marc Fourmigue
FARADAY DISCUSSIONS
(2017)
Article
Chemistry, Physical
Emmanuel Aubert, Enrique Espinosa, Irene Nicolas, Olivier Jeannin, Marc Fourmigue
FARADAY DISCUSSIONS
(2017)
Article
Chemistry, Multidisciplinary
Irene Nicolas, Christian Bijani, Denis Brasseur, Genevieve Pratviel, Jean Bernadou, Anne Robert
COMPTES RENDUS CHIMIE
(2013)
Article
Electrochemistry
Matthieu Picot, Irene Nicolas, Cyril Poriel, Joelle Rault-Berthelot, Frederic Barriere
ELECTROCHEMISTRY COMMUNICATIONS
(2012)
Article
Engineering, Chemical
M. Picot, R. Rodulfo, I. Nicolas, A. Szymczyk, F. Barriere, M. Rabiller-Baudry
JOURNAL OF MEMBRANE SCIENCE
(2012)
Article
Engineering, Chemical
Anthony Szymczyk, Yonis Ibrahim Dirir, Matthieu Picot, Irene Nicolas, Frederic Barriere
JOURNAL OF MEMBRANE SCIENCE
(2013)
Article
Chemistry, Organic
Irene Nicolas, Ksenija Kisseljova, Patrick Bauchat, Michele Baudy-Floc'h
Article
Chemistry, Organic
Paul Le Maux, Irene Nicolas, Soizic Chevance, Gerard Simonneaux
Article
Chemistry, Inorganic & Nuclear
Irene Nicolas, Soizic Chevance, Paul Le Maux, Gerard Simonneaux
TETRAHEDRON-ASYMMETRY
(2010)
Article
Biochemistry & Molecular Biology
Noella Germain-Amiot, Yoann Augagneur, Emilie Camberlein, Irene Nicolas, Valerie Lecureur, Astrid Rouillon, Brice Felden
NUCLEIC ACIDS RESEARCH
(2019)
Article
Biochemistry & Molecular Biology
Irene Nicolas, Valerie Bordeau, Arnaud Bondon, Michele Baudy-Floc'h, Brice Felden
Article
Chemistry, Multidisciplinary
Emmanuel Aubert, Irene Nicolas, Olivier Jeannin, Marc Fourmigue, Enrique Espinosa
Summary: The strength of halogen bonding is influenced by the substituents of the molecules involved, and the position of the bromine atom within the adduct can be controlled by external electric fields.
CRYSTAL GROWTH & DESIGN
(2023)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
