Article
Chemistry, Organic
Meng-Cheng Zhang, Dong-Chao Wang, Gui-Rong Qu, Hai-Ming Guo
Summary: The first catalytic asymmetric route to synthesize chiral thiohydantoins containing a quaternary stereogenic center has been established using a chiral phosphoric acid catalyst, achieving high yields and excellent enantioselectivities. This reaction also allows for the construction of two C-N bonds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Inorganic & Nuclear
Wei-Dong Yu, Yin Zhang, Yu-Yang Han, Bin Li, Sai Shao, Le-Ping Zhang, Hong-Ke Xie, Jun Yan
Summary: Four new tris-Anderson polyoxometalates were synthesized and studied for their catalytic properties in the reaction between CO2 and epoxides. The research achieved certain results in this area.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Amu Wang, Ya-Zhou Liu, Zhongke Shen, Zeen Qiao, Xiaofeng Ma
Summary: A TEMPO-mediated [3 + 2] annulation-aromatization protocol for the preparation of pyrazolo[1,5-a]pyridines has been developed, offering good to excellent yields with high and predictable regioselectivity. The modification of marketed drugs and a one-pot three-step gram scale synthesis of a key intermediate for Selpercatinib preparation have been demonstrated.
Article
Chemistry, Organic
Mamta Gill, Arko Das, Vinod K. Singh
Summary: An enantioselective (3+2) cycloaddition reaction has been reported for the synthesis of chiral polysubstituted pyrrolidines. The reaction displays opposite regioselectivity with excellent enantioselectivities and yields. Interestingly, changing the alpha-substituents of the iminoesters results in the formation of normal (3+2) cycloaddition products with excellent enantioselectivities as well.
Article
Chemistry, Organic
Matthew J. Mailloux, Gabrielle S. Fleming, Shruti S. Kumta, Aaron B. Beeler
Summary: A unified approach to azepines via dearomative photochemical rearrangement of aromatic N-ylides is described, yielding mono- and polycyclic azepines in high yields. This ring-expansion technique provides a new mode of access to functionalized azepines from N-heteroarenes with only two straightforward steps and simple starting materials.
Article
Biochemistry & Molecular Biology
Yasushi Yoshida, Hidetoshi Ida, Takashi Mino, Masami Sakamoto
Summary: 1,2,4-Triazole and 1,2,4-triazoline are important components in bioactive molecules and catalysts for organic synthesis. Efficient synthesis of these components has been extensively studied, but their structural diversity remains underexplored. In this study, we demonstrate a formal [3 + 2] cycloaddition reaction between α-imino esters and azo compounds under Bronsted base catalysis, yielding 1,2,4-triazolines in high yields. This reaction allows the general preparation of 3-aryl pentasubstituted 1,2,4-triazolines for the first time, regardless of the steric and electronic properties of the substrates and reactants. Mechanistic studies suggest that the reaction proceeds without isomerization into the aldimine form.
Article
Chemistry, Organic
Vladimir A. Motornov, Andrey A. Tabolin, Yulia V. Nelyubina, Valentine G. Nenajdenko, Sema L. Ioffe
Summary: A new efficient method for the synthesis of multifunctionalized pyrrolidines via copper-catalyzed diastereoselective [3 + 2]-cycloaddition was developed, leading to the formation of novel fluorinated heterocycles like beta-fluoro-beta-nitropyrrolidines. The products exhibited good to excellent yields and high diastereoselectivity, and subsequent transformations resulted in the synthesis of medicinally attractive beta-fluoro-NH-pyrroles and other derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Yi-Xian Li, Jun-Zhe Wang, Yuna Shimadate, Maki Kise, Atsushi Kato, Yue-Mei Jia, George W. J. Fleet, Chu-Yi Yu
Summary: The C-7 fluorinated derivatives of casuarine and australine, important polyhydroxylated pyrrolizidines, were successfully synthesized using organocatalytic stereoselective alpha-fluorination of aldehydes as a key step. This strategy can also be applied to the synthesis of challenging fluorinated iminosugars and carbohydrates. Docking studies revealed that the potent inhibitions of trehalase and amyloglucosidase by the fluorinated polyhydroxylated pyrrolizidines are mainly due to the interaction of fluorine atoms in these iminosugars with the amino acid residues of the corresponding enzymes. Additionally, unusual anion-pi interactions were established between the C-7 fluoride and a hydrophobic pocket in amyloglucosidase. These unexpected docking modes and structure-activity relationship studies highlight the significance of fluorination in the design of polyhydroxylated pyrrolizidine glycosidase inhibitors.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Chunmao Dong, Weiwei Peng, Huan Wang, Xiao Zhang, Jun Zhang, Guishan Tan, Kangping Xu, Zhenxing Zou, Haibo Tan
Summary: A remarkable base-promoted methodology has been discovered for the rapid construction of (E)- and (Z)-gamma-oxo-alpha,beta-alkenoic ester skeletons from easily accessible vinyl propargylic alcohols through modified redox isomerization. This approach demonstrates high simplicity and efficiency with excellent tolerance of functional substituents, allowing for straightforward structural modifications of various natural products and efficient total syntheses of melodienone, homomelodienone, isomelodienone, and homoisomelodienone within 4 linear steps.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Physical
Venkatachalam Vijayalakshmi, Narayanasamy Nivetha, Arumugam Thangamani
Summary: A short and efficient multicomponent sequence for synthesizing spiroacenaphthylene pyrrolizidine analogs 5a-s via 1,3-dipolar cycloaddition reaction without any catalyst was developed. The synthesized compounds were characterized by spectral data and single crystal X-ray diffraction study. Some of the compounds exhibited favorable anti-leukemia activity, molecular docking interaction, and in-silico ADME properties.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Applied
Laura Boetje, Xiaohong Lan, Fitrilia Silvianti, Jur van Dijken, Michael Polhuis, Katja Loos
Summary: This study presents a series of starch esters synthesized through transesterification reactions catalyzed by TBD in DMSO. By purging the reaction flask with nitrogen, the degree of substitution was increased. Long-chain fatty acids exhibited the most significant increase in DS, while starch esters from unsaturated fatty acids showed lower Tg and higher hydrophobicity compared to pristine starch.
CARBOHYDRATE POLYMERS
(2022)
Article
Chemistry, Organic
Cui Wei, Zhou Zhou, Guang-Li Pang, Cui Liang, Dong-Liang Mo
Summary: A variety of oxazabicyclo[4.2.1]nonanone derivatives were synthesized in good yields through a cascade reaction, involving several steps, and a single-pot reaction. Mechanistic studies revealed the reaction pathway and the role of the catalyst in achieving the desired products.
Article
Chemistry, Inorganic & Nuclear
Alexander Kaps, Herbert Plenio
Summary: The cycloaddition reactions of substituted anthracenes with nosylated quinone imines provide a convenient route to triptycenes. After re-aromatization, O-butylation and cleavage of the nosyl-group, triptycene anilines are obtained and converted into imidazolium salts. Deprotonation of the imidazolium salts result in novel triptycene-NHC-metal complexes with unusual ligand sterics.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Asaad S. Mohamed, Fatma H. Al-Awadhi, Nouria A. Al-Awadi
Summary: This study reports the synthesis of a family of 14 new syn/anti bis-4-spiro-fi-lactam-based unsaturated macrocycles, with structural identification including NMR and HRMS spectral data and single-crystal X-ray diffraction analysis. The synthesis involved multistep synthesis methods, such as diimine formation, Staudinger [2 + 2] ketene-imine cycloaddition, and ring-closing metathesis (RCM).
Article
Chemistry, Multidisciplinary
Tian-Ming Liao, Wen-Jiang Ma, Yu-Ning Gao, Ming Bian, Min Jiang, Jin-Tao Liu, Hui-Yu Chen, Zhen-Jiang Liu
Summary: This study presents two green and facile protocols for the synthesis of polyfluoroalkanesulfinyl or alkylsulfinyl 4-isoxazolines. Various aldehyde and ketone derived nitrones reacted with alpha-alkynyl sulfoxides under catalyst- and solvent-free conditions at room temperature, providing a series of polyfluoroalkanesulfinyl or alkylsulfinyl 4-isoxazolines with high efficiency. The synthesis was further improved to a one-pot process in aqueous medium, eliminating the need for isolating the nitrones. These reactions offer easy and environmentally friendly methods for the preparation of sulfinyl 4-isoxazolines.
Article
Chemistry, Organic
Ting Pan, Pan Shi, Bo Chen, Da-Gang Zhou, Ya-Li Zeng, Wen-Dao Chu, Long He, Quan-Zhong Liu, Chun-An Fan
Article
Chemistry, Organic
Shi-Yi Yuan, Qi-Qi Yan, Dan Wang, Ting-Ting Dan, Long He, Cheng-Yu He, Wen-Dao Chu, Quan-Zhong Liu
Summary: A new method for the asymmetric synthesis of 3-methyleneindolines from alkynyl imines has been developed via a rhodium-catalyzed tandem process, which shows unconventional chemo-selectivity and provides products with high yields and enantioselectivities under mild reaction conditions, perfect atom economy, and a broad substrate scope.
Article
Chemistry, Organic
Wen-Dao Chu, Tian -Tian Liang, Hao Ni, Zhi-Hong Dong, Zhihui Shao, Yong Liu, Cheng-Yu He, Ruopeng Bai, Quan-Zhong Liu
Summary: In this study, we describe a Pd(0)-catalyzed intermolecular asymmetric dearomative [3 + 2] annulation of phenols with vinyl cyclopropanes through the in situ generation of ortho-quinone methide intermediates. Highly functionalized spiro-[5,6] bicycles with three contiguous stereogenic centers, including an all-carbon quaternary, were obtained with excellent stereoselectivities. Density functional theory (DFT) calculations suggest that the reactions are controlled by thermodynamics.
Article
Chemistry, Organic
Wen-Dao Chu, Ya-Ting Wang, Tian-Tian Liang, Teng Long, Jia-Yu Zuo, Zhihui Shao, Bo Chen He, Cheng-Yu He, Quan-Zhong Liu
Summary: Vinylcyclopropanes (VCPs) are versatile building blocks in organic synthesis, capable of generating 1,3-dipoles and undergoing [3 + 2] cycloaddition reactions. While asymmetric reactions between VCPs and electron-deficient olefins have been well developed, enantioselective reactions involving alkenes with weak electron-withdrawing groups, particularly alkenyl N-heteroarenes, remain unexplored.
Article
Chemistry, Organic
Xue-Hua Deng, Jia-Xi Jiang, Qin Jiang, Ting Yang, Bo Chen, Long He, Wen-Dao Chu, Cheng-Yu He, Quan-Zhong Liu
Summary: In this study, the asymmetric cross reductive coupling reaction of conjugated dienes and ketoimines using copper hydride as a catalyst was achieved for the first time. The reaction, catalyzed by chiral Ph-BPE ligand, provides a rapid and efficient access to homoallylic amines with two vicinal stereogenic centers.
Article
Chemistry, Organic
Wen-Dao Chu, Chun-Mei Wang, Jie Zhan, Ya-Li Zeng, Yong Liu, Bo Chen, Kaiming Zhang, Cheng-Yu He, Quan-Zhong Liu
Summary: This paper reports the copper-catalyzed 1,4-addition of a silicon nucleophile to azadienes. This method easily provides a wide variety of dibenzylic silane derivatives in good to excellent yields. The important practical features include the use of a cheap catalytic system, mild reaction conditions, and broad substrate scope.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Cheng-Yu He, Wen-Dao Chu, Quan-Zhong Liu, Ting Yang, Qin Jiang, Chun-Mei Wang, Song-Liang Li
Summary: An unprecedented cycloaddition reaction of vinyl diazo compounds with benzofuran-derived azadienes catalyzed by rarely independently used NaBArF4 has been achieved. Benzofuran-fused hydropyridines were synthesized with excellent yields and high diastereoselectivity through a Na+-catalyzed inverse-electron-demand azaDiels-Alder reaction. Notably, this transformation also allows for the one-pot synthesis of the spiro[benzofurancyclopentene] skeleton, exhibiting perfect atom economy and simple reaction conditions.
Article
Chemistry, Organic
Qin Jiang, Ting Yang, Qi Li, Guang-Ming Liang, Yong Liu, Cheng-Yu He, Wen-Dao Chu, Quan-Zhong Liu
Summary: A Lewis acid Sc(OTf)3-catalyzed annulation reaction has been reported for the synthesis of indole-fused tricyclic rings by reacting vinyl diazoacetates with in situ formed alpha,beta-unsaturated imines. This strategy involves a sequential addition/rebound addition process of vinyl diazoacetates and an in situ dedinitrogenation. The annulation protocol offers advantages such as low-cost catalysts, mild reaction conditions, and easily prepared substrates.
Article
Chemistry, Organic
Teng Long, Ya-Li Zeng, Zhi-Hong Dong, Shu Li, Jie Zhan, Sheng-Min Zeng, Jia-Li Qiu, Wen-Dao Chu, Quan-Zhong Liu
Summary: A nickel-catalyzed three-component alkylarylation reaction using alkenyl N-heteroarenes, alpha-bromocarboxylates, and aryl boronic acids has been developed. It provides a new strategy for the synthesis of N-heteroarene substituted diarylalkanes with moderate to good yields. The reaction conditions are mild and the catalyst is cheap, making it a practical and efficient method for accessing various alkylaryl compounds.
Article
Chemistry, Organic
Wen-Dao Chu, Chun-Mei Wang, Shu Li, Zhi-Hong Dong, Teng Long, Jia-Xi Jiang, Bo Chen, Cheng-Yu He, Quan-Zhong Liu
Summary: The intermolecular reductive radical coupling of olefins with alkenyl N-heteroarenes, employing an iron(iii)-catalyzed hydrogen atom transfer strategy, is described. The important practical features include the use of a cheap catalytic system, mild reaction conditions, high functional group tolerance, and broad substrate scope.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Shan Xiao, Bo Chen, Qin Jiang, Long He, Wen-Dao Chu, Cheng-Yu He, Quan-Zhong Liu
Summary: A novel synthetic method has been discovered, which involves palladium-catalyzed asymmetric cycloaddition to efficiently synthesize highly functionalized and optically enriched aza-spiroindolenines. This method achieves yields of up to 83%, with up to 97% ee and a dr of 13:1.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Organic
Bo Chen, Cheng-Yu He, Wen-Dao Chu, Quan-Zhong Liu
Summary: Enantioselective desymmetrization and kinetic resolution are powerful strategies for constructing enantiomerically enriched cyclohexanone-containing molecules, showing significant progress, especially in transition metal catalysis and asymmetric kinetic resolution. Remaining challenges and future perspectives are briefly discussed.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Ya-Li Zeng, Bo Chen, Ya-Ting Wang, Cheng-Yu He, Zi-Yuan Mu, Ji-Yuan Du, Long He, Wen-Dao Chu, Quan-Zhong Liu
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Organic
Qing Zhou, Bo Chen, Xiao-Bing Huang, Ya-Li Zeng, Wen-Dao Chu, Long He, Quan-Zhong Liu
ORGANIC CHEMISTRY FRONTIERS
(2019)
Article
Chemistry, Multidisciplinary
Bo Chen, Wen-Dao Chu, Quan-Zhong Liu
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
