Article
Chemistry, Multidisciplinary
Xiaolei Li, Jicheng Wu, Weiping Tang
Summary: Human glycans are mainly composed of nine common sugar building blocks, while hundreds of different monosaccharides have been found in bacteria. A new efficient strategy has been developed to access rare sugars from common monosaccharides, which can be used for constructing glycoside skeletons in natural products or bioactive compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Applied
Eri Ogino, Satoru Kuwano, Takayoshi Arai
Summary: In this study, chiral catalyst AMB2 was used to successfully catalyze the asymmetric epoxidation of acrylonitriles, resulting in highly enantioselective chiral epoxides.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Weiming Chen, Xin Xie, Jian Zhang, Jian Qu, Can Luo, Yaozhu Lai, Feng Jiang, Han Yu, Yongge Wei
Summary: An efficient method for the carbon-carbon bond cleavage of 1,2-diols using an iron catalyst in acetic acid with hydrogen peroxide as the oxidant was reported. The method showed high conversion rate and selectivity, and was also efficient in degrading renewable biomass oleic acid.
Article
Chemistry, Multidisciplinary
Zhiliang Huang, Renpeng Guan, Elliot L. Bennett, Jianliang Xiao
Summary: This study discovered a photo-promoted catalytic system that efficiently oxidizes 1,2-diols to produce valuable compounds, while tolerating a wide range of functional groups.
Article
Chemistry, Physical
Qing-Shan Kong, Xing-Long Li, Hong-Bo Shen, Hua-Jian Xu, Yao Fu
Summary: This study presents an eco-friendly and efficient heterogeneous sodium-doped porous sodium manganese oxide catalyst for the oxidative cleavage of furanic 1,2-diols into medium-chain furanic aldehyde compounds. Various high value-added chemicals were synthesized using this catalytic approach, demonstrating its broad applicability and high selectivity.
GREEN ENERGY & ENVIRONMENT
(2022)
Article
Chemistry, Multidisciplinary
Xu-Long Qin, Ang Li, Fu-She Han
Summary: The P-stereogenic phosphinamides have been demonstrated as powerful organocatalysts for the desymmetric enantioselective reduction of cyclic 1,3-diketones, providing a useful method for the synthesis of chiral cyclic 3-hydroxy ketones. The protocol shows a broad substrate scope and high enantioselectivities and diastereoselectivities for the chiral cyclic 3-hydroxy ketone products. Mechanistic studies revealed that an intermediate formed from P-stereogenic phosphinamide and catecholborane is the real catalytically active species, which paves the way for designing and developing other reactions using P-stereogenic phosphinamides as new organocatalysts.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Shihao Su, Guojun Lv, Xuyang Zou, Jiangzhang Wang, Chaoyi Zhou, Yan Chen, Jialing Shen, Yangbin Shen, Zhongmin Liu
Summary: This study reports the use of byproduct carboxylic acid as a catalyst for converting cyclic alkenes into 1,2-diols, achieving effective utilization of the byproduct and energy consumption savings. The synthesized beta-MnO2 catalyst is an active and stable heterogeneous catalyst for the tandem conversion of cyclic alkenes into 1,2-diols, demonstrating high conversion rates and yields. A plausible mechanism for the tandem conversion reaction is proposed and verified.
Article
Chemistry, Organic
Taeok Kim, Michael R. Bell, V. Narasimharao Thota, Todd L. Lowary
Summary: This study reports a one-pot strategy for functionalizing pyranoside 1,2-cis-diols with two different ester protecting groups. The approach selectively acylates through orthoester hydrolysis promoted by a carboxylic acid, and after removal of water and introduction of a coupling agent, the carboxylic acid is esterified with the liberated hydroxyl group. Although applied to 1,2-cis-diols on pyranoside scaffolds, this method can be applicable to similar motifs on any six-membered ring.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Materials Science, Multidisciplinary
T. V. M. Sreekanth, X. Wei, K. Yoo, J. Kim
Summary: In this study, Co3O4 catalyst was synthesized by annealing ZIF-67 and characterized for its properties. The results showed that compared to ZIF-67, the ZIF-67-derived Co3O4 catalyst exhibited lower Tafel-slope value and higher electrocatalytic performance in urea electro-oxidation.
MATERIALS CHEMISTRY AND PHYSICS
(2023)
Article
Chemistry, Organic
Rui Wang, Pengchao Sun, Weiwei Jin, Yonghong Zhang, Bin Wang, Yu Xia, Fei Xue, Ablimit Abdukader, Chenjiang Liu
Summary: This paper developed two efficient methods for the oxidative cleavage of C-C single bonds of vicinal tertiary diols and discussed their advantages and limitations. The results of the study demonstrate that the organic electrosynthesis method is greener and more efficient.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Colton R. Davis, Irungu K. Luvaga, Joseph M. Ready
Summary: Alkenyl boronates react with Ir(pi-allyl) intermediates to form products with high enantioselectivity, establishing multiple C-C bonds. The reaction provides tertiary boronic esters that can undergo multiple functionalizations. Extension to trisubstituted olefins results in the formation of three contiguous stereocenters.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Polymer Science
Badr M. Thamer, Meera Moydeen Abdulhameed, Mohamed H. El-Newehy
Summary: In this study, a non-precious NiCoFe trimetallic catalyst supported on porous carbon (NiCoFe@PC) was successfully prepared using gelation and pyrolysis method. The catalyst showed remarkable electrocatalytic activity and low onset potential for urea oxidation in an alkaline medium, outperforming many other transition bimetallic/trimetallic catalysts previously reported.
Article
Chemistry, Multidisciplinary
Yongbing Liu, Huanlin Diao, Guorong Hong, Jonathan Edward, Tao Zhang, Guoqiang Yang, Bin-Miao Yang, Yu Zhao
Summary: We have developed an enantioconvergent approach to chiral N-heterocycles using racemic diols and primary amines via cost-effective borrowing hydrogen annulation. The discovery of a chiral amine-derived iridacycle catalyst was crucial for achieving high efficiency and enantioselectivity in the one-step formation of two C-N bonds. This catalytic method provides quick access to a diverse range of enantioenriched pyrrolidines, including key precursors for valuable drugs like aticaprant and MSC 2530818.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Erik T. Ouellette, Marshall G. Lougee, Andrea R. Bucknam, Paul J. Endres, John Y. Kim, Emma J. Lynch, Elizabeth J. Sisko, Bianca R. Sculimbrene
Summary: The study focused on phosphoryl transfer desymmetrization of ten prochiral diols using a titanium-BINOLate complex, achieving yields of 50-98% for nine 1,3-propane diols and high enantiomeric ratios for diols with a quaternary C-2 center. The evaluation of chiral ligand, base, solvent, and stoichiometry supported an active catalyst oligomeric in chiral ligand, with pyrophosphates facilitating enantioselective phosphorylation with desired protecting groups on the phosphate product.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Meijuan Yuan, Xiaotian Guo, Nan Li, Huan Pang
Summary: By utilizing biomass materials, optimal catalytic properties for the urea electro-oxidation reaction were achieved, resulting in lower potential and higher efficiency for energy conversion.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2021)
Review
Chemistry, Multidisciplinary
Zijuan Yan, Pan-Lin Shao, Qing Qiang, Feipeng Liu, Xuchao Wang, Yongjie Li, Zi-Qiang Rong
Summary: This article summarizes various mechanisms and reaction conditions for the transition metal-catalyzed conversion of aldehydes to ketones.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Yaru Gao, Luo-Yu Wang, Tao Zhang, Bin-Miao Yang, Yu Zhao
Summary: We present a highly efficient method for the synthesis of axially chiral 1,1'-bipyrroles. The method involves the use of simple hydrazine and 1,4-diones as starting materials and further derivatization to obtain axially chiral bifunctional compounds with high potential in asymmetric catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Gang Liao, Tao Zhang, Liang Jin, Bing-Jie Wang, Cheng-Kai Xu, Yu Lan, Yu Zhao, Bing-Feng Shi
Summary: In this study, we investigated the directing ability of chalcogenoether motifs in Pd-catalyzed atroposelective C-H functionalization through experimental and DFT computational studies. The results showed that the thioether motif exhibited superior reactivity and enantioselectivity compared to the corresponding ether and selenoether. Notably, DFT calculations provided a predictive model for optimizing reaction conditions and interpreting the origin of enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Zijuan Yan, Feipeng Liu, Xuchao Wang, Qing Qiang, Yongjie Li, Yao Zhang, Zi-Qiang Rong
Summary: The facile synthetic method presented involves the construction of amides from alcohols and amines catalyzed by Ni/NHC, with advantages such as base metal catalysis, commercially available catalyst, good yields (up to 95%), and substrate generality. The nature of the reaction was revealed through NMR spectroscopy and isolation of intermediates.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Teng Wei Ng, Ran Tao, Willy Wei Li See, Si Bei Poh, Yu Zhao
Summary: In this study, a catalytic borrowing hydrogen method was disclosed, which enables the efficient synthesis of enantiopure tetrahydropyridines by coupling substrates with 1,3-amino alcohols. Highly diastereoselective functionalizations of tetrahydropyridines also result in the synthesis of enantiopure di- and tri-substituted piperidines, which are commonly found in commercial drugs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Si-Chen Zhang, Shengping Liu, Xia Wang, Shao-Jie Wang, Hui Yang, Lin Li, Binmiao Yang, Ming Wah Wong, Yu Zhao, Shenci Lu
Summary: We report an unprecedented stereoselective synthesis of triaryl-2pyrones from readily available starting materials. This method involves the atroposelective annulation of 2-aryketones with ynals under oxidative conditions. The annulation allows the construction of one or two axes in a single operation and affords axially chiral triaryl-2-pyrones with high enantioselectivity.
Article
Chemistry, Organic
Dan Hu, Si Bei Poh, Feipeng Liu, Zhifeng Tu, Xia Wang, Shenci Lu, Yu Zhao
Summary: The effect of counter-anions on enantio-control in oxidative NHC catalysis is systematically investigated in this study. The results demonstrate that the identity of counter-anions has a significant impact on the enantioselectivity of the catalytic system, and highly efficient kinetic resolution can be achieved by selecting appropriate counter-anions.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Yongbing Liu, Huanlin Diao, Guorong Hong, Jonathan Edward, Tao Zhang, Guoqiang Yang, Bin-Miao Yang, Yu Zhao
Summary: We have developed an enantioconvergent approach to chiral N-heterocycles using racemic diols and primary amines via cost-effective borrowing hydrogen annulation. The discovery of a chiral amine-derived iridacycle catalyst was crucial for achieving high efficiency and enantioselectivity in the one-step formation of two C-N bonds. This catalytic method provides quick access to a diverse range of enantioenriched pyrrolidines, including key precursors for valuable drugs like aticaprant and MSC 2530818.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Xuchao Wang, Jing Xue, Zi-Qiang Rong
Summary: This study reports a highly efficient catalyst-tuned regio- and enantioselective hydroalkylation reaction for the divergent synthesis of chiral C2- and C3-alkylated pyrrolidines. The reaction uses readily available catalysts and chiral ligands to synthesize enantioenriched compounds with excellent regio- and enantioselectivity. It also demonstrates compatibility with complex substrates derived from a series of drugs and bioactive molecules, providing a distinct entry to more functionalized chiral N-heterocycles.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Luo-Yu Wang, Jiapei Miao, Yu Zhao, Bin-Miao Yang
Summary: We developed a highly selective method for synthesizing 1,1'-biheteroaryls bearing a chiral N-N axis. By using chiral phosphoric acid and InBr3 as cooperative catalysts, 2,3-diketoesters reacted with 1,3-dione-derived enamines to construct 1,1'-pyrrole-indoles with high enantioselectivity, up to 92% yield, and up to 94% enantiomeric excess (ee), or bisindoles with up to 92% ee. Derivatizations of these compounds resulted in diverse functionalized N-N linked axially chiral biheteroaryls.
Article
Chemistry, Multidisciplinary
Xiao Qian Ng, Yu Zhao, Valerio Isoni
Summary: This study presents a sustainable and scalable hydrogen borrowing synthesis of amine drugs with low heavy metal content. Despite the challenges in this strategy, the developed approach emphasizes atom economy and eliminates the need for toxic solvents, resulting in a realistic green alternative for synthetic application in Pharma. The synthesized commercial drugs exhibit good to excellent PMI values and the intensified nature of the process leads to high productivity.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Review
Chemistry, Multidisciplinary
Yaru Gao, Guorong Hong, Bin-Miao Yang, Yu Zhao
Summary: Direct substitution of readily available alcohols is an important area of research in green chemical synthesis. Catalytic enantioconvergent transformations of racemic secondary alcohols are desired for efficient access to valuable enantiopure compounds. The enantioconvergent borrowing hydrogen methodology has proven to be effective for achieving such transformations. This review provides an overview of the progress made in the past decade, focusing on the conversion of racemic secondary alcohols to enantioenriched chiral amines, N-heterocycles, higher-order alcohols, and ketones.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Organic
Luo-Yu Wang, Jiapei Miao, Yu Zhao, Bin-Miao Yang
Summary: We report a highly selective abbreviation for the efficient synthesis of 1,1'-biheteroaryls. Under the cooperative catalysis of chiral phosphoric acid and InBr3, reactions between 2,3-diketoesters and 1,3-dione-derived enamines resulted in the highly enantioselective construction of 1,1'-pyrrole-indoles with up to 92% yield and 94% enantiomeric excess. Derivatizations of these compounds to diverse functionalized N-N linked axially chiral biheteroaryls have also been demonstrated.
Article
Chemistry, Organic
Na Bai, Xuchao Wang, Zhenchao Wang, Feipeng Liu, Zi-Qiang Rong
Summary: This paper reports a ruthenium-catalyzed cross-coupling reaction of long-range alkenyl alcohols with amines, achieving remote site-selective functionalization through a chain-walking strategy. The method exhibits good yields and functional group tolerance.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Jinglin Qu, Zijuan Yan, Xuchao Wang, Jun Deng, Feipeng Liu, Zi-Qiang Rong
Summary: Aryl ketones, an important class of organic compounds, are widely used in the synthesis of pharmaceuticals, biologically active molecules, and functional materials. This study presents a facile synthetic method for the construction of aryl ketones through Ni-catalyzed cross coupling of epoxides with aryltriflates, resulting in highly regioselective conversion with good yields in a redox neutral manner.
CHEMICAL COMMUNICATIONS
(2022)
