Article
Chemistry, Multidisciplinary
Jia-Bin Pan, Zhi-Chun Yang, Xuan-Ge Zhang, Mao-Lin Li, Qi-Lin Zhou
Summary: Here, we present a method for enantioselective phosphoric acid catalyzed amination of ketenes generated from α-aryl-α-diazoketones. Mechanistic studies elucidated the reaction pathway and explained how the catalyst expedited the transformation and controlled the enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Sheng-Qiang Guo, Hui-Qing Yang, Yu-Zhen Jiang, Ai-Lian Wang, Guo-Qiang Xu, Yong-Chun Luo, Zhao-Xu Chen, Haixue Zheng, Peng-Fei Xu
Summary: In this study, a green and reliable strategy for the diastereoselective synthesis of beta-amido sulfones through organophotoredox catalytic four-component radical-polar crossover cascade reactions was reported. The transformation exhibited excellent atom-, step-, and redox economy as well as diastereoselectivity.
Article
Chemistry, Organic
Marine Pinaud, Leila Vaitilingom, Gayathiri Gnanalingam, Tania Xavier, Erwan Le Gall, Marc Presset
Summary: The use of N-alkyl imines in decarboxylative Mannich reaction with substituted malonic acids half oxyesters (SMAHOs) has been developed to afford a direct access to secondary beta(2,3)-aminoesters. The transformation occurs under very practical conditions (DABCO as a catalyst in bulk toluene and open to air) and can be performed with a broad range of each substrate in yields of 36 to 97 %. Importantly, the reaction was found to require the use of acidic additives in combination with the organocatalyst to limit the competitive olefination reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ze-Shu Wang, Lu-Jing Zhu, Cui-Ting Li, Bin-Yang Liu, Xin Hong, Long-Wu Ye
Summary: In recent years, there has been significant attention on the asymmetric catalysis of ynamides, with most reactions focused on central chirality. However, the synthesis of axially chiral compounds from ynamides has been limited to noble-metal catalysis. This study presents a metal-free protocol for the construction of axially chiral N-heterocycles from ynamides using chiral Bronsted acid-catalyzed 5-endo-dig cyclization. The method allows for the practical and atom-economical synthesis of valuable N-arylindoles with excellent enantioselectivities, and the resulting axially chiral N-arylindole skeletons can be employed in asymmetric catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Camran Ali, Donna G. Blackmond, Jordi Bures
Summary: Nonlinear effects can be observed in asymmetric catalytic cascade reactions without the involvement of higher order catalyst species or reaction steps involving two catalyst species. This may be due to the disruption of pre-equilibria in reversible steps prior to the final irreversible product formation step.
Review
Chemistry, Organic
Divyang M. Patel, Paras J. Patel, Hitendra M. Patel
Summary: This Review discusses pioneering advances in catalytic stereoselective multicomponent reactions for the preparation of spiro derivatives, highlighting the stereoselective reactions and catalytic mechanisms used in different reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Dong-Hua Xie, Cheng Niu, Da-Ming Du
Summary: In this paper, a new protocol for building a chiral ring-fused chroman skeleton was developed through organocatalytic asymmetric Michael addition/hemiketalization cascade reactions. The reactions provided chiral chroman-fused pyrrolidinediones with high yields and excellent stereoselectivities. A scale-up synthesis was also conducted, and a possible reaction mechanism was proposed.
Article
Chemistry, Multidisciplinary
En Li, Jiean Chen, Yong Huang
Summary: The Michael reaction is an important method for preparing functional molecules with a β-stereogenic center. However, the enantioselective seleno-Michael addition is still poorly explored. In this study, a highly enantioselective Michael addition reaction of alkyl selenols to enones was reported, introducing a Se atom asymmetrically to an electron-deficient double bond. A chiral bifunctional N-heterocyclic carbene (NHC)/thiourea catalyst was developed and showed remarkable selectivity in delivering chiral β-seleno ketones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Applied
Sara Meninno, Francesca Franco, Maurizio Benaglia, Alessandra Lattanzi
Summary: Pyrazoleamides have gained attention as reactive and practical surrogates in asymmetric catalysis, particularly in a variety of metal- and organocatalytic transformations. Their relevance has extended to photoredox catalysis and challenging stereoselective bond-forming reactions in recent years.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Sevilya N. Yunusova, Alexander S. Novikov, Natalia S. Soldatova, Mikhail A. Vovk, Dmitrii S. Bolotin
Summary: Hypervalent iodine(iii)-derivatives have higher catalytic activity than other aliphatic and aromatic iodine(i)- or bromine(i)-containing substrates for a Knorr-type reaction, with dibenziodolium triflate showing the highest activity for generating N-acyl pyrazoles. The catalytic activity of iodine(iii) is attributed to its binding with a ketone, as indicated by H-1 NMR titration data and DFT calculations.
Article
Multidisciplinary Sciences
Yu-Hua Wen, Zi-Jing Zhang, Shuai Li, Jin Song, Liu-Zhu Gong
Summary: The authors have developed a method to construct four stereoisomers of oxindoles with high enantioselectivity and diastereoselectivity using cooperative copper- and organocatalysis. The ability to precisely control the reactive site planar in the region is of great importance in asymmetric stereodivergent catalysis. This method provides a new strategy for the synthesis of chiral functional molecules and has potential applications in alkaloid synthesis.
NATURE COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Jun Kikuchi, Masahiro Terada
Summary: The development of enantioselective catalysis using organocatalysts has become a prominent research field, with recent advancements in enantioconvergent substitution reactions despite challenges.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Zan Yang, Xun Zhang, Yu Jiang, Qiang Ma, Saihu Liao
Summary: The properties of poly(vinyl ether)s depend significantly on their tacticity, with considerable efforts focused on developing stereoselective cationic polymerization methods for isotactic PVEs. Current methods using metal-based Lewis acids have limitations on catalyst loading and monomer scope. A metal-free stereoselective cationic polymerization of vinyl ethers has been introduced using chiral confined Bronsted acids, offering advantages such as high efficiency, high stereoselectivity, and simplicity in operation.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Wei Liu, Tianren Qin, Wansen Xie, Jinmiao Zhou, Zidan Ye, Xiaoyu Yang
Summary: We have developed an efficient modular asymmetric synthesis of azahelicenes from readily available polycyclic aromatic amines, aldehydes, and (di)enamides, employing a central-to-helical chirality conversion strategy. A series of aza[5]- and aza[4]helicenes bearing various substituents were easily obtained with good yields and high enantioselectivities. The diverse derivatizations and the preliminary application of the azahelicene derivative as a chiral organocatalyst demonstrated the potential of this method, and the photophysical and chiroptical properties of these azahelicenes were well studied, showing potential applications in novel organic optoelectronic materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Yong-Liang Su, Geng-Xin Liu, Luca De Angelis, Ru He, Ammar Al-Sayyed, Kirk S. Schanze, Wen-Hao Hu, Huang Qiu, Michael P. Doyle
Summary: This study demonstrates the efficient generation of functionalized derivatives through photocatalyzed multicomponent reactions using nitrogen aromatic heterocycles, alkenes, and diazo compounds. The reaction shows high functional group tolerance and exacting regioselectivities. Mechanistic studies, including photophysical measurements, provide insights into this radical cascade reaction.
Article
Medical Laboratory Technology
Yang Xiao, Jiebin Xie, Lan Liu, Wentao Huang, Qiang Han, Jiayi Qin, Shunying Liu, Zhen Jiang
Summary: This study identified NSDHL and NCEH1 as useful biomarkers for screening, diagnosis, and prognosis of patients with gastric cancer using iTRAQ-labeled quantitative proteomics. The combination of NSDHL and NCEH1 showed good performance in terms of sensitivity and specificity.
JOURNAL OF CLINICAL LABORATORY ANALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Dan Ni, Longlong Song, Yun Zhao, Shunying Liu
Summary: A Rh(II)/boron reagent co-catalyzed transformation was developed for the efficient synthesis of multi-substituted conjugated dienones under mild conditions. By trapping allene carbocations with oxonium ylides, two C=C double bonds, one C-C single bond, and one C-O single bond were constructed in yields up to 85%. Furthermore, a diversity-oriented strategy was established for the synthesis of alkyne ether and dihydrofuran derivatives in a substrate-dependent manner.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Medicinal
Yaqi Deng, Rou Pi, Li Niu, Yun Zhao, Dan Ni, Longlong Song, Zi Li, Wangyujing Han, Qinghua Wei, Yuqiao Han, Tong Zhu, Zhengli Luo, Donghui Sun, Suzhen Dong, Shunying Liu
Summary: This study identified a potential drug candidate for the treatment of osteosarcoma, which demonstrated significant cellular potency and in vivo efficacy by modulating the solubility of compounds. The candidate compound also showed inhibition of OS cell migration.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Jian Ji, Cong Guan, Qinghua Wei, Xuwen Chen, Yun Zhao, Shunying Liu
Summary: This study developed a highly regioselective synthesis of N-2-substituted 1,2,3-triazoles using N-sulfonyl-1,2,3-triazoles and alkyl bromides/alkyl iodides at room temperature. The mechanistic pathway proposed explains the high N-2 regioselectivity, and the protocol showed good to excellent product yields (72-90%).
Article
Chemistry, Organic
Xiangrong Liu, Xue Tian, Jiawu Huang, Yu Qian, Xinfang Xu, Zhenghui Kang, Wenhao Hu
Summary: An enantioselective three-component reaction of alpha-propargylic-3-indolymethanol with diazoindolinone and alcohol has been achieved under the cocatalysis of Rh(II) and chiral phosphoric acid (CPA). The reaction proceeds through regio- and enantiospecific addition of an in situ formed oxonium ylide to the alpha-propargylic indole iminium ion, providing an efficient access to chiral propargylic indole derivatives with high yields and enantioselectivities.
Article
Chemistry, Organic
Cong Guan, Jian Ji, Zi Li, Qinghua Wei, Xiang Wu, Shunying Liu
Summary: An efficient one-pot two-step synthetic strategy has been developed for the highly selective synthesis of N-2-substituted-1,2,3-triazole via a radical transformation from aryl ethynylenes, azides, and furan. A total of 17 examples of aryl ethynylene with different substituents were successfully converted into their corresponding functionalized N-2-substituted-1,2,3-triazole derivatives with good yields.
Article
Chemistry, Physical
Yong-Liang Su, Geng-Xin Liu, Luca De Angelis, Ru He, Ammar Al-Sayyed, Kirk S. Schanze, Wen-Hao Hu, Huang Qiu, Michael P. Doyle
Summary: This study demonstrates the efficient generation of functionalized derivatives through photocatalyzed multicomponent reactions using nitrogen aromatic heterocycles, alkenes, and diazo compounds. The reaction shows high functional group tolerance and exacting regioselectivities. Mechanistic studies, including photophysical measurements, provide insights into this radical cascade reaction.
Article
Chemistry, Organic
Xiang Fu, Jie Tang, Ruyu Hua, Xiaoqian Li, Zhenghui Kang, Huang Qiu, Wenhao Hu
Summary: This study reports two DNA-compatible reactions with alkenes and diazo compounds, providing hydroalkylation and cyclopropanation products in moderate to excellent yields. These transformations not only offer new access to C(sp3)-C(sp3) bond formation in DELs with excellent functional group tolerance, but also represent practical ligation methods to introduce functionalized molecules into DNA.
Letter
Chemistry, Organic
Jian Xue, Zhengli Luo, Jisheng Huang, Yaqi Deng, Suzhen Dong, Shunying Liu
Summary: An asymmetric catalytic approach for the construction of C3-multifunctionalization alpha-hydroxy-beta-amino pyridines has been developed. The method utilizes two chiral catalysts to modulate the reaction independently, leading to high yield and good enantioselectivity. The resulting products exhibit selective antiosteosarcoma activity on 143B cells.
Article
Chemistry, Physical
Longlong Song, Lulu Xiong, Dan Ni, Weixiong Chen, Jian Ji, Jian Xue, Xuwen Chen, Xiang Wu, Xiao He, Shunying Liu
Summary: Here, we report a [Pd-(eta(3)-C3H5)-Cl](2)/Sc-(OTf)(3)-catalyzed catalytic process accelerated by Bronsted acids with a beta-selective aza-Michael addition to yield a gamma-quaternary carbon. The triple co-catalytic system provides a strategy for the activation of vinyl-quinolines with a linear selectivity containing gamma-quaternary carbon, and the developed method shows a broad substrate scope, providing a general and rapid strategy for the quinoline-based diverse library construction.
Article
Chemistry, Organic
Cong Guan, Jiabin Yin, Jian Ji, Jinhua Liu, Xiang Wu, Tong Zhu, Shunying Liu
Summary: A regioselective electrochemical C-H amination method using easily accessible ethers has been developed to synthesize N (2)-substituted 1,2,3-triazole. Multiple substituents, including heterocycles, were well-tolerated, and 24 examples were obtained in moderate to good yields. Control experiments and DFT calculations revealed that the electrochemical synthesis occurs through a N-tosyl 1,2,3-triazole radical cation process, promoted by single-electron transfer from the lone pair electrons of the aromatic N-heterocycle, and the desulfonation is responsible for the high N (2)-regioselectivity.
Article
Chemistry, Multidisciplinary
Jian Ji, Zongjing Hu, Cong Guan, Jinhua Liu, Yaqi Deng, Xuwen Chen, Shunying Liu
Summary: An efficient method for the 1,2-carbotriazolization of alkenes with N-sulfonyl-1,2,3-triazoles and aldehydes has been developed using a copper-catalyzed radical relay process. This strategy enables the production of beta-triazolized ketones with high regio- and chemoselectivity, and has a wide substrate scope. The resulting beta-triazolized ketone scaffold shows promising inhibitory activity on osteosarcoma cell lines, making it a potential pharmacophore for drug discovery.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Physical
Longlong Song, Lulu Xiong, Dan Ni, Weixiong Chen, Jian Ji, Jian Xue, Xuwen Chen, Xiang Wu, Xiao He, Shunying Liu
Summary: This study reports a [Pd(eta 3-C3H5)Cl]2/Sc(OTf)3 catalytic system accelerated by Brønsted acids for the selective aza-Michael addition of vinyl-substituted quinolines, diazos, and anilines/alcohols. The activation of the corresponding Lewis acid by the generation of anhydride analogues from Brønsted acid and the counter anion (OTf-) promotes nearly quantitative transformation. The triple co-catalytic system provides a strategy for the activation of vinylquinolines with a linear selectivity containing gamma-quaternary carbon.
Article
Chemistry, Organic
Ji Jian, Liu Jinhua, Guan Cong, Chen Xuwen, Zhao Yun, Liu Shunying
Summary: The green and efficient synthesis of N-2-substituted 1,2,3-triazoles was achieved by coupling cheap and easily available alcohols with N-sulfonyl-1,2,3-triazole using in-situ generated sulfonic acid as a catalyst. The reaction exhibited high regioselectivity and good yields without the need for additional catalysts or additives. Mechanistic studies suggested that the reaction was promoted by methanesulfonic acid (MsOH) generated from the hydrolysis of N-sulfonyl-1,2,3-triazoles, and high regioselectivity was achieved through a thermally stable intermediate.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhengli Luo, Xuwen Chen, Jian Xue, Yaqi Deng, Suzhen Dong, Shunying Liu
Summary: A method has been developed for the rapid and efficient synthesis of benzosultams containing continuous quaternary carbons in a one-pot fashion, with moderate to excellent yields at room temperature. The resulting products exhibit good anticancer activity in osteosarcoma cells.
ORGANIC CHEMISTRY FRONTIERS
(2022)
