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, Multidisciplinary
Alexandra Hindle, Krzysztof Baj, Jonathan A. Iggo, Daniel J. Cox, Christopher M. Pask, Adam Nelson, Stephen P. Marsden
Summary: A convergent approach to diazabicyclic scaffolds containing twisted amides or anilines is achieved through photocatalysed hydroamination and subsequent cyclisation of cyclic enecarbamates. The modular synthesis enables variation of the degree of twist and consequently the properties of the amides and anilines.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Muxing Zhou, Tatiana Gridneva, Zhenfeng Zhang, Ende He, Yangang Liu, Wanbin Zhang
Summary: This study presents an efficient route for the synthesis of chiral phthalidyl ester prodrugs using a chiral bicyclic imidazole organocatalyst and a continuous injection process. Computational studies suggest a general base catalytic mechanism different from the widely accepted nucleophilic catalytic mechanism. Analysis of key transition states reveals that CH-pi interactions, rather than previously considered cation/pi-pi interactions, play a dominant role in stereocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Raul Porcar, Eduardo Garcia-Verdugo, Belen Altava, Maria Isabel Burguete, Santiago V. Luis
Summary: Chiral imidazolium l-prolinate salts have been studied as green and efficient chiral organocatalysts for direct asymmetric aldol reactions at room temperature. The presence of chirality in both the imidazolium cation and prolinate anion plays a significant role in transferring chirality from the organocatalyst to the aldol product. By selecting proper structural elements in the cation and anion, excellent activities, selectivities, and enantioselectivities can be achieved.
Review
Chemistry, Organic
Zhao-Ying Yang, Ming Zhang, Xiao-Chen Wang
Summary: The development of chiral borane Lewis acid catalysts has allowed for transition-metal-free catalyzed asymmetric organic reactions. In this study, we have summarized our work on the preparation of two classes of novel chiral bicyclic bisborane Lewis acid catalysts derived from C-2-symmetric [3.3.0] dienes and [4.4] dienes. These catalysts not only catalyze asymmetric hydrogenation reactions through frustrated Lewis pairs with Lewis bases, but also activate Lewis basic functional groups in traditional Lewis acid catalyzed asymmetric reactions.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Zhanglin Shi, Chaoren Shen, Kaiwu Dong
Summary: The palladium-catalyzed diastereoselective hydroesterification reaction was used to synthesize chiral gamma-butyrolactones with two stereocenters, and a route was developed to transform alkenes with single chiral center to chiral THF-fused bicyclic gamma-lactones containing three stereocenters using carbonylation-lactonization products as key intermediates.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Jia-Yu Zou, Yu-Ying Yang, Jun Gu, Fei Liu, Zhiwen Ye, Wenbin Yi, Ying He
Summary: In this study, we reported a regio- and atroposelective synthesis method for axially chiral N-vinylquinazolinones. Through the strategy of asymmetric allylic substitution-isomerization, combined with asymmetric transition-metal catalysis and organocatalysis, both trisubstituted and tetrasubstituted N-vinylquinazolinone atropisomers were efficiently synthesized.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jia-Yu Zou, Yu-Ying Yang, Jun Gu, Fei Liu, Zhiwen Ye, Wenbin Yi, Ying He
Summary: This study reports the regio- and atroposelective synthesis of axially chiral N-vinylquinazolinones using the strategy of asymmetric allylic substitution-isomerization. Both Z- and E-tetrasubstituted axially chiral N-vinylquinazolinones were obtained with high yields and enantioselectivities through the careful design of allylic substrates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Julian Full, Santosh P. Panchal, Julian Gotz, Ana-Maria Krause, Agnieszka Nowak-Krol
Summary: Helically chiral compounds with one and two boron atoms were synthesized using a modular approach, showing exceptional configurational stability and fluorescence properties. The compounds are proposed as primary structures of extended helices, with potential applications in materials science.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Mingxu Li, Jian Zhang, Yashi Zou, Fengfan Zhou, Zhenfeng Zhang, Wanbin Zhang
Summary: Asymmetric hydrogenation of unsaturated morpholines has been achieved using a bisphosphine-rhodium catalyst with a large bite angle, resulting in quantitative yields and excellent enantioselectivities (up to 99% ee) of various 2-substituted chiral morpholines. The hydrogenated products can be converted into key intermediates for bioactive compounds.
Article
Chemistry, Applied
Michal Domanski, Jonas Zurauskas, Joshua P. Barham
Summary: A continuous flow auto-frequency tuning single-mode microwave reactor is presented as a powerful platform for synthesizing alkyl imidazolium salts as ionic liquids/ionic liquid precursors. The reactor achieves near-quantitative yields, high productivities, and record space-time yields, and addresses challenges such as viscosity changes, dielectric property changes, and phase separations.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Physical
Tengfei Wang, Danning Zheng, Beibei An, Yi Liu, Tiegang Ren, Hans Agren, Li Wang, Jinglai Zhang, Marten S. G. Ahlquist
Summary: We report a novel dual-ionic imidazolium salt catalyst that exhibits efficient catalytic activity for the cycloaddition of carbon dioxide and epoxides under environmentally friendly conditions, without the need for solvent and co-catalyst, with a yield as high as 96.1%. The catalyst can be reused multiple times with a yield maintained above 90%. Theoretical calculations and experimental measurements support a new reaction mechanism involving a CO2-philic group and an electrophilic hydrogen atom in the catalyst. Our findings suggest that incorporating CO2-philic groups is a feasible approach to develop new efficient ionic liquids.
GREEN ENERGY & ENVIRONMENT
(2022)
Article
Polymer Science
Wei Cao, Liangxiao Tan, Hong Wang, Jiayin Yuan
Summary: Dual-cationic PIL homopolymers carrying both imidazolium and 1,2,4-triazolium moieties were synthesized by exploiting the reactivity difference, leading to the expansion of their application spectrum.
Article
Chemistry, Multidisciplinary
Wee Li Mah, Xiu Jun Tan, Kar Bee Choo, Shiaw Xian Lee, Kong Wai Tan, Keng Yoon Yeong, Sui Mae Lee, Yuen Lin Cheow
Summary: This study synthesized a series of pyridine-functionalized (benz)imidazolium salts and found that some of the compounds exhibited good antimicrobial and anticancer properties. The use of microwave irradiation significantly reduced the reaction time.
Article
Chemistry, Multidisciplinary
Qian Su, Xin Tan, Xiaoqian Yao, Ting Ying, Li Dong, Mengqian Fu, Weiguo Cheng, Suojiang Zhang
Summary: Using 2-carboxylated imidazolium salts as catalysts for the hydration of epoxides into 1,2-diols showed high efficiency and selectivity in the experiment, depending on the interaction between different cation chain lengths and anions. Salts with shorter chains exhibited better thermal stability and catalytic performance, reducing the formation of byproducts and increasing the yield. The research results were further confirmed and explained by XPS analysis and DFT calculations, proposing a cation-anion synergistic mechanism.
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)
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)
Article
Chemistry, Multidisciplinary
Yuta Shikata, Risa Yasue, Kazuhiro Yoshida
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
