Article
Chemistry, Multidisciplinary
Min Wen, William Erb, Florence Mongin, Marielle Blot, Thierry Roisnel
Summary: Enantiopure ferrocene-1,2-disulfoxide derivatives have been synthesized using the rational use of directed deprotometallation, sulfur oxidation, and sulfoxide/lithium exchange. They not only represent the first members of this original family, but some of them have shown promise as ligands in rhodium-catalysed conjugate addition.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Fuad O. Usman, Achyut R. Gogoi, Jason C. Mixdorf, Osvaldo Gutierrez, Hien M. Nguyen
Summary: In this study, an enantioselective synthesis of 1,2-disubstituted allylic fluorides using a chiral diene-ligated rhodium catalyst was reported. Kinetic studies and calculations were conducted to investigate the molecular structure and reaction kinetics of the formation process of 1,2-disubstituted allylic fluorides. The reaction selectivity and yield of the construction process of 1,2-disubstituted allylic fluorides were also identified.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Chao Dong, Dao-Sheng Liu, Lei Zhang, Xiang-Ping Hu
Summary: An enantioselective Rh-catalyzed hydrogenation of E/Z mixtures of trisubstituted vinyl esters has been achieved using a chiral ferrocenylphosphine-phosphoramidite ligand. The reaction showed high yields and good to high enantioselectivities, with the presence of a small amount of t-butanol benefiting the hydrogenation outcome.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Applied
Masatoshi Yamada, Tomoaki Kato, Tomomi Ikemoto, Mitsuhisa Yamano
Summary: A highly efficient rhodium-catalyzed asymmetric hydrogenation of a sterically hindered tetrasubstituted enamine was developed, providing quick and efficient access to a key synthetic chiral intermediate in the route to an active pharmaceutical ingredient. The new rhodium catalyst showed full conversion and high enantioselectivity in the asymmetric hydrogenation of the substrate, with P-31 NMR study conducted to characterize the catalyst.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Review
Chemistry, Multidisciplinary
Johanna Vondran, Marc R. L. Furst, Graham R. Eastham, Thomas Seidensticker, David J. Cole-Hamilton
Summary: The bidentate phosphine ligand 1,2-DTBPMB is known as one of the best ligands for alkoxycarbonylation reactions, providing high selectivity and catalytic activity at low temperatures.
Article
Chemistry, Inorganic & Nuclear
Kristina Zivkovic, Lilia M. Baldauf, Jessica L. Cryder, Alexa Villasenor, Valeria Reyes, Lauren E. Bernier, Theresa J. Thomas, Maxwell O'Toole, Kayleen Fulton, Curtis E. Moore, Arnold L. Rheingold, Christopher J. A. Daley
Summary: The study reports the first isolation and structural characterization of a series of chiral trinitrogen pincer ligands, as well as the methods for their preparation. Experimental results show that a novel microwave-based technique is more efficient, although currently not scalable.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Multidisciplinary
Guang-Ya Zhang, Sun-Hong Ruan, Yan-Yun Li, Jing-Xing Gao
Summary: The study investigated the asymmetric transfer hydrogenation of a wide range of ketones catalyzed by manganese complex and chiral PxNy-type ligand under mild conditions. By using 2-propanol as a hydrogen source and combining [MnBr(CO)(5)] with chiral, 22-membered macrocyclic ligand (R,R,R',R')-CyP2N4 (L5) with 2% catalyst loading, various ketones could be enantioselectively hydrogenated to afford highly valuable chiral alcohols with up to 95% ee.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Yi-Xuan Ding, Zhou-Hao Zhu, Mu-Wang Chen, Chang-Bin Yu, Yong-Gui Zhou
Summary: In this study, the asymmetric hydrogenation of all-carbon aromatic rings was achieved using rhodium/diphosphine catalysts. The introduction of chiral diphosphine ligands with steric hindrance and strong electron-donating properties was key to the success in obtaining axially chiral cyclic compounds with high enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Physical
Racha Abed Ali Abdine, Gaspard Hedouin, Francoise Colobert, Joanna Wencel-Delord
Summary: This review summarizes the achievements in the field of metal-catalyzed asymmetric direct hydrogenation of nonactivated and activated imines. It provides a summary of reported catalytic systems with their reactivity, selectivity, limitations, and discusses the effects of certain reaction conditions on the enantioselectivity of imine hydrogenation, as well as analysis of proposed imine hydrogenation mechanisms.
Article
Chemistry, Multidisciplinary
Luo Ge, Syuzanna R. Harutyunyan
Summary: Chiral bisphosphine ligands play a key role in transition-metal-catalyzed asymmetric synthesis. However, the commonly used transition metals are expensive and scarce, and the synthesis of chiral phosphine ligands is complex. In this study, a catalytic asymmetric hydrophosphination reaction using a chiral complex of earth-abundant manganese(i) was developed. This reaction provides a short and efficient synthetic route to access easily obtainable and structurally tunable chiral bisphosphines, which can be used in asymmetric catalysis with earth-abundant metal-based organometallic catalysts.
Article
Chemistry, Organic
Yongjie Shi, Jingxin Wang, Qin Yin, Xumu Zhang, Pauline Chiu
Summary: An asymmetric 1,2-reduction of cyclic alpha,beta-unsaturated ketones was achieved under mild conditions, catalyzed by in situ generated copper hydride ligated with (R)-DTBM-C-3*-TunePhos. The reaction produced various enantiomerically enriched cyclic allylic alcohols, with up to 98% ee enantioselectivities for alpha-brominated cydoalkenones and moderate enantioselectivities for substrates without alpha-substituents.
Article
Chemistry, Multidisciplinary
Lei Yang, Wen-Qiang Xu, Tao Liu, Yichen Wu, Biqin Wang, Peng Wang
Summary: The synthesis of a Si-centered spirocyclic skeleton, SPOSiOL, and its derived chiral ligands were reported in this study, showcasing their potential in transition metal-catalyzed asymmetric reactions. This finding emphasizes the value of Si-centered spirocyclic scaffolds in asymmetric catalysis.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Lixian Wang, Jin Lin, Chungu Xia, Wei Sun
Summary: This study presents a manganese-catalyzed enantioselective transfer hydrogenation method for the synthesis of chiral hydrazines. The method exhibits wide substrate compatibility and high enantioselectivity, and it is applicable to challenging diaryl hydrazones.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Johnathan Bowen, Carla Slebodnick, Webster L. Santos
Summary: We report an organocatalytic trans hydroboration of 3-substituted-propiolonitriles. In the presence of catalytic amounts of tributylphosphine and pinacolborane, regioselective hydroboration of the internal triple bond proceeded in a stereoselective fashion under mild conditions to afford the corresponding (E)-1,2-vinylcyanoborane derivatives. The mechanism is proposed to occur through a 1,2-phosphine addition instead of a canonical 1,4-conjugate addition pathway.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Inorganic & Nuclear
Prashant Kumar
Summary: Binuclear rhodium(I) complexes based on a pyridylalkylamine ligands were synthesized and explored for the asymmetric hydrogenation of aromatic ketones. The results showed efficient and selective synthesis of chiral alcohols.
INORGANIC CHEMISTRY COMMUNICATIONS
(2022)
Article
Chemistry, Inorganic & Nuclear
Hao Hu, Wei-Yi Wu, Tamotsu Takahashi, Kazuhiro Yoshida, Masamichi Ogasawara
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2017)
Review
Chemistry, Organic
Kohei Watanabe, Takashi Mino, Eri Ishikawa, Miyu Okano, Tatsuya Ikematsu, Yasushi Yoshida, Masami Sakamoto, Kazuki Sato, Kazuhiro Yoshida
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Inorganic & Nuclear
Risa Yasue, Masaru Miyauchi, Kazuhiro Yoshida
TETRAHEDRON-ASYMMETRY
(2017)
Review
Chemistry, Multidisciplinary
Kazuhiro Yoshida, Risa Yasue
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Inorganic & Nuclear
Risa Yasue, Kazuhiro Yoshida
Article
Chemistry, Organic
Yuya Miwa, Takumi Kamimura, Kiyoaki Sato, Daichi Shishido, Kazuhiro Yoshida
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Waka Takagaki, Risa Yasue, Kazuhiro Yoshida
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2020)
Article
Chemistry, Organic
Shuta Sakai, Kazuki Sato, Kazuhiro Yoshida
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Physical
Kazuhiro Yoshida, Qiang Liu, Risa Yasue, Shiro Wada, Ryosuke Kimura, Takuma Konishi, Masamichi Ogasawara
Article
Chemistry, Organic
Jun-ichi Ueda, Yuuki Enomoto, Mizuki Seki, Takuma Konishi, Masamichi Ogasawara, Kazuhiro Yoshida
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Applied
Risa Yasue, Kazuhiro Yoshida
Summary: By utilizing rhodium-catalyzed C-H bond amination, optically active amino acids containing the adamantane core were synthesized with high enantiomeric excess up to 85%. The enantioenriched products demonstrated synthetic utility as chiral building blocks, being converted into a dipeptide derivative and a Schiff-base ligand. The absolute configuration of one amino acid derivative was confirmed by X-ray single-crystal structure analysis.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Mizuki Seki, Kazuhiro Yoshida
Summary: A new chiral rhodium catalyst was synthesized and fully characterized, showing good catalytic activity and enantioselectivity in asymmetric reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Aya Saito, Kazuhiro Yoshida, Hideo Togo
Summary: Treatment of N-propargyl-N'-tosylhydrazines with molecular iodine (I-2) in the presence of NaHCO3 under warming conditions efficiently afforded the corresponding 5-substituted 4-iodo-1-tosylpyrazoles, while the same reaction in the presence of acetic acid generated the corresponding 5-aryl-4-iodopyrazoles.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Kazuki Ito, Shuta Sakai, Kazuhiro Yoshida
Summary: The reaction of 3-arylbenzo[b]thiophenes and elemental sulfur to obtain [1]benzothieno[2,3-b][1]benzothiophenes (BTBTs) is reported. The addition of molecular iodine is essential for the reaction, and it enables the formation of the desired products with high yield and purity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Risa Yasue, Masaru Miyauchi, Kazuhiro Yoshida
ADVANCED SYNTHESIS & CATALYSIS
(2017)