Article
Chemistry, Organic
Linan Hou, Sheng Zhang, Ji Ma, Haiyu Wang, Tienan Jin, Masahiro Terada, Ming Bao
Summary: An organocatalytic atroposelective strategy for the construction of axially chiral compounds containing benzimidazole and quinoline rings is introduced. The reaction of 2-alkynylbenzimidazoles with ortho-aminophenylketones proceeds smoothly in the presence of chiral phosphoric acid, resulting in axially chiral heterobiaryls with good yields and enantioselectivities. This paper presents the first example of combining benzimidazole and quinoline rings at the 2- and 3-positions, respectively, into axially chiral heterobiaryls using this new strategy.
Article
Chemistry, Multidisciplinary
Shuai Zhu, Jian-Hui Mao, Jun Kee Cheng, Shao-Hua Xiang, Bin Tan
Summary: Studies of axial chirality are an important part of modern chemistry research, and this paper describes a method for exploiting chiral molecules. Through two efficient synthetic strategies, structurally diverse analogs can be synthesized with excellent stereocontrol. These findings expand the current library of axially chiral compounds and provide new directions for exploring other axially chiral molecules with different skeletal frameworks.
Article
Biochemistry & Molecular Biology
Christos Matsingos, Taha Al-Adhami, Shirin Jamshidi, Charlotte Hind, Melanie Clifford, J. Mark Sutton, Khondaker Miraz Rahman
Summary: The issue of antimicrobial resistance and the lack of new antibiotics for treating multidrug-resistant bacteria present a significant challenge in public health. Research on the structure-activity relationships of the C5-acylaminomethyl moiety of the oxazolidinone antibiotic linezolid has provided valuable insights into the development of new antibiotics. The study suggests that modifications at this specific position are crucial for the function of antibiotics in this class.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Shengli Huang, Haojun Wen, Yuhong Tian, Pengfei Wang, Wenling Qin, Hailong Yan
Summary: This study presents an effective method for the enantioselective preparation of polychiral compounds by intramolecular introduction of multiple stereogenic elements using organocatalysis. The compounds synthesized show potential applications in optoelectronic materials and heavy metal ion detection, as indicated by their optical properties and Ru3+-induced fluorescence responses.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Ying Wang, Yang Yang, Shiyu Xu, Aima Huang, Lu Chen, Yubao Xie, Pengyutian Liu, Liang Hong, Guofeng Li
Summary: This paper presents an intramolecular annulation strategy for the synthesis of heterocycloalkenyl atropisomers using organocatalysis, resulting in the successful preparation of various (1H)-isochromen-1-imines with good to excellent yields and high enantioselectivity. These compounds can be easily converted to atropisomeric lactones isocoumarins, demonstrating their potential for further exploration in the development of bioactive compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Applied
Chandrakanta Parida, Siddharth K. K. Dave, Kousik Das, Subhas Chandra Pan
Summary: A catalytic asymmetric dearomatization reaction of b-naphthols with 4-aryl-1,2,4-triazole-3,5-diones is disclosed. A chiral phosphoric acid with spiro motif was found to be effective for this reaction. The reaction afforded chiral urazole embedded naphthalenones with both axial and central chirality in good to high yields (70-85%) and high diastereo- and enantioselectivities (>20:1, 8-96% ees).
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Shihui Luo, Jun (Joelle) Wang
Summary: In Angewandte Chemie, Wang, Song, and co-workers proposed a new and practical organocatalysis method to synthesize axially chiral pyrazole-based phosphorus scaffolds. They achieved the central-to-axial chirality conversion in the Huisgen-type cycloaddition reaction by using a dipeptide-phosphonium salt catalyst with very low catalyst loading (1 mol %).
Review
Chemistry, Multidisciplinary
Wei Tan, Jia-Yi Zhang, Cong-Hui Gao, Feng Shi
Summary: Chiral seven-membered ring systems are widely present in natural products and pharmaceuticals, therefore, the catalytic enantioselective construction of such frameworks has attracted significant interest in the field of chemistry. Among the various approaches, organocatalytic asymmetric (4+3) cycloadditions are highly effective. This review summarizes the progress in this field from 2003 to early 2022 and provides insights into challenging issues, aiming to facilitate future developments.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yuxiao Duan, Meng Chen, Hironobu Hayashi, Hiroko Yamada, Xinyue Liu, Lei Zhang
Summary: We report the synthesis of a novel buckybowl with a high bowl-to-bowl inversion barrier, allowing the formation of two chiral polycyclic aromatic hydrocarbons. By strategically fusing eight-membered rings to the rim of the buckybowl, chiral hybrids are synthesized with helicity and positive and negative curvature. These hybrids exhibit configurational stability and intriguing optoelectronic properties, including a high binding affinity towards C-60.
Article
Multidisciplinary Sciences
Yu Chang, Chuandong Xie, Hong Liu, Shengli Huang, Pengfei Wang, Wenling Qin, Hailong Yan
Summary: 1,2-Azoles are privileged structures in many natural products and drugs. The authors report an atroposelective synthesis of two types of axially chiral 1,2-azoles through vinylidene ortho-quinone methide intermediates.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Xianfang Hong, Jingcheng Guo, Jinhua Liu, Wei Cao, Chenlong Wei, Ye Zhang, Xiaoxiang Zhang, Zhenqian Fu
Summary: This study successfully achieved organocatalytic dynamic kinetic resolution of configurationally labile N-arylindole lactams for the first time, providing an efficient method for the construction of a structurally diverse set of axially chiral molecules bearing a tetra-ortho-substituted C-N chiral axis. This strategy features compatibility with various skeletons, mild reaction conditions, easy scale-up, and excellent atom economy.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Biotechnology & Applied Microbiology
Ying-Cheng Liao, Boonyawee Saengsawang, Jun-Wei Chen, Xiao-Zhen Zhuo, Si-Yu Li
Summary: An antibiotic- and inducer-free culture condition was proposed for polyhydroxybutyrate (PHB) production in recombinant E. coli. Through the construction of antibiotic-free vectors and the insertion of the putative phaCAB operon, PHB production without the need for antibiotics or inducers was achieved. Additionally, the insertion of an efficient E. coli rho factor-independent terminator helped avoid possible transcriptional carry-over.
FRONTIERS IN BIOENGINEERING AND BIOTECHNOLOGY
(2022)
Article
Chemistry, Organic
Shiqi Jia, Wenling Qin, Pengfei Wang, Hailong Yan
Summary: An organocatalytic methodology has been developed for the construction of axially chiral nonsymmetric biaryltriols with high efficiency and selectivity. The synthesized biaryltriols can be used as chiral ligands for preparing chiral sec-alcohols and as organocatalysts for asymmetric Petasis reactions. Additionally, they show potential as selective fluorescent sensors for Ru3+ ions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Huaiyu Bin, Li Cheng, Xiaohui Yang, Jianhua Xie, Qilin Zhou
Summary: The study presents a concise strategy for the enantioselective construction of the pyridine-fused chiral bicyclo[3.3.1]nonane skeleton of (+)-huperzine A and its analogues. Key features include catalytic asymmetric hydrogenation and intramolecular arylation, allowing for a rapid and efficient synthesis route from known starting materials.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Tomohiro Sugahara, Daisuke Hashizume, Norihiro Tokitoh, Hiroshi Matsui, Ryohei Kishi, Masayoshi Nakano, Takahiro Sasamori
Summary: This study presents the experimental visualization of the valence-electron-density distribution in benzene and its kinetically stabilized heavier-element analogues, 1,2-disilabenzene and 1,2-digermabenzene. The analysis indicates that the 1,2-disilabenzene and 1,2-digermabenzene have lower aromaticity compared to benzene due to the presence of incompletely delocalized pi electrons on their cyclic conjugation systems.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2022)
Article
Chemistry, Multidisciplinary
Josef M. Maier, Ping Li, Erik C. Vik, Christopher J. Yehl, Sharon M. S. Strickland, Ken D. Shimizu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Review
Chemistry, Organic
Jung Wun Hwang, Ping Li, Ken D. Shimizu
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Josef M. Maier, Ping Li, Jackson S. Ritchey, Christopher J. Yehl, Ken D. Shimizu
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Multidisciplinary
Jungwun Hwang, Ping Li, Mark D. Smith, Constance E. Warden, Dominic A. Sirianni, Erik C. Vik, Josef M. Maier, Christopher J. Yehl, C. David Sherrill, Ken D. Shimizu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Correction
Chemistry, Multidisciplinary
Jungwun Hwang, Ping Li, William R. Carroll, Mark D. Smith, Perry J. Pellechia, Ken D. Shimizu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Multidisciplinary
Ping Li, Erik C. Vik, Josef M. Maier, Ishwor Karki, Sharon M. S. Strickland, Jessica M. Umana, Mark D. Smith, Perry J. Pellechia, Ken D. Shimizu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Polymer Science
Meghan E. Lamm, Ping Li, Samuel Hankinson, Tianyu Zhu, Chuanbing Tang
Article
Chemistry, Multidisciplinary
Erik C. Vik, Ping Li, Perry J. Pellechia, Ken D. Shimizu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Organic
Erik C. Vik, Ping Li, Daniel O. Madukwe, Ishwor Karki, Gabriel S. Tibbetts, Ken D. Shimizu
Summary: The study found that the interaction between carbonyl oxygens and the pi-face of aromatic surfaces could stabilize transition states but was weaker compared to other interactions. This interaction was mainly driven by electrostatic forces with only a small contribution from orbital delocalization.
Article
Chemistry, Multidisciplinary
Ping Li, Joshua T. Damron, Gabriel M. Veith, Vyacheslav S. Bryantsev, Shannon M. Mahurin, Ilja Popovs, Santa Jansone-Popova
Summary: A novel bifunctional organic network, capable of capturing both chromium and arsenic in water through ion exchange and redox processes, has been developed. This network shows high efficiency and maintains a balanced uptake ratio of Cr/As.
Article
Nanoscience & Nanotechnology
Ping Li, Joshua T. Damron, Vyacheslav S. Bryantsev, Katherine R. Johnson, Diana Stamberga, Shannon M. Mahurin, Ilja Popovs, Santa Jansone-Popova
Summary: In this study, the structure-activity relationship in the adsorption and removal of chromium- and arsenic-based oxoanions in water by guanidinium-based ionic organic covalent nanosheets (iCONs) was investigated. Structural modulations in iCONs were found to alter the guanidinium acidity, regulating the oxoanion uptake limits via ion exchange. Hydrogen bonding, steric, and electrostatic interactions at/near the guanidinium-based anion binding site in iCONs heavily influenced the uptake efficiency and selectivity of arsenate but not chromate.
ACS APPLIED NANO MATERIALS
(2021)
Article
Chemistry, Multidisciplinary
Alexander N. Manzewitsch, Hao Liu, Binzhou Lin, Ping Li, Perry J. Pellechia, Ken D. Shimizu
Summary: An empirical model was developed to predict organic solvophobic effects based on measurements of N-phenylimide molecular balances. The model takes into account the intramolecular alkyl-alkyl interactions in the folded conformers and the systematic variation of alkyl group lengths. Linear correlations were observed between organic solvophobic effects and solvent cohesive energy density (CED) as well as changes in solvent-accessible surface areas (SASA). The model accurately predicts the organic solvophobic interaction energy per unit area for any organic solvent with known CED values and has been verified against experimental measurements.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Ping Li, Erik C. Vik, Ken D. Shimizu
ACCOUNTS OF CHEMICAL RESEARCH
(2020)
Article
Chemistry, Multidisciplinary
Erik C. Vik, Ping Li, Josef M. Maier, Daniel O. Madukwe, Vitaly A. Rassolov, Perry J. Pellechia, Eric Masson, Ken D. Shimizu
Article
Chemistry, Organic
Jungwun Hwang, Ping Li, Erik C. Vik, Ishwor Karki, Ken D. Shimizu
ORGANIC CHEMISTRY FRONTIERS
(2019)
