Article
Biochemistry & Molecular Biology
Hongwen Mu, Yan Jin, Rongrong Zhao, Liming Wang, Ying Jin
Summary: In this study, bifunctional Takemoto's catalysts were used to catalyze the enantioselective Michael reaction of aminomaleimides with nitroolefins. The resulting products showed good yields and high enantiomeric excess.
Article
Chemistry, Organic
Chandan K. Mahato, Sayan Mukherjee, Mrinalkanti Kundu, Virbhadra P. Vallapure, Animesh Pramanik
Summary: This study utilized a new set of organic catalysts for asymmetric Michael reactions in water, achieving high efficiency and yield, offering a new method for green synthesis. The strategy also successfully synthesized an optically active octahydroindole, a key component found in many natural products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Amol B. Gorde, Anas Ansari, Ramesh Ramapanicker
Summary: New molecules were designed and synthesized to improve the catalytic ability of the catalyst, resulting in high catalytic activity and stereoselectivity under optimized conditions. The studies showed high yields of Michael adducts with excellent enantioselectivities and diastereoselectivities in a wide range of aldehydes and beta-nitrostyrenes.
Article
Chemistry, Organic
Zhi-Cheng Huang, Min Xiang, Wen-Sheng Li, Ying Zou, Chen-Yi Li, Jian Zhang, Xia Li, Fang Tian, Li-Xin Wang
Summary: A new type of spirooxindole scaffolds were effectively synthesized as organocatalysts through enantioselective reaction, with high yield and ee value. The reaction has been successfully scaled up to gram scale and most typical organocatalysts were further purified up to 99% ee by recrystallization.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Shi-Jie Zhu, Zhi-Feng Hao, Ya Pan, Ying Zhou, Xiong-Li Liu, Ming Zhang, Chuan-Wen Lei
Summary: In this study, a stepwise enantioselective formal (3 + 2) cyclocondensation reaction was successfully accomplished, leading to the synthesis of spiro-fused pentacyclic spirooxindoles. The reaction showed good overall yields, excellent dr, and high ee values.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Shi-Jie Zhu, Zhi-Feng Hao, Ya Pan, Ying Zhou, Xiong-Li Liu, Ming Zhang, Chuan-Wen Lei
Summary: The first enantioselective formal (3 + 2) cyclocondensation involving alpha,fi-unsaturated pyrazoleamides as 3-carbon partners was successfully achieved in a stepwise fashion. The protocol led to the synthesis of spiro-fused pentacyclic spirooxindoles with good overall yields, excellent diastereomeric ratios, and high enantiomeric excess values.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Naoki Sakai, Kyohei Kawashima, Masashi Kajitani, Seiji Mori, Takeshi Oriyama
Summary: This study reported the first asymmetric Michael addition of alpha-aminomaleimides as Michael donors to beta-nitrostyrenes using an organocatalyst derived from a Cinchona alkaloid. Density functional theory investigations were crucial for improving the enantioselectivity of the adduct.
Article
Chemistry, Organic
Qian Chen, Hao Sun, Linlin Li, Jie Tian, Qian Xu, Nana Ma, Li Li, Lin Zhang, Chun Li
Summary: The asymmetric hydrogenation of alpha-halogenated ketones with iridium catalyst using cinchona-alkaloid-based NNP ligands has been developed, allowing the efficient synthesis of chiral halohydrins with a wide substrate scope and high enantioselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhehui Liao, Jiantao Zhang, Tongxiang Cao, Shifa Zhu
Summary: A series of highly strained bicyclo[3.n.1]alkenones have been successfully synthesized with good-to-excellent enantioselectivities and moderate-to-good yields via copper-catalyzed formal [3+3] cycloaddition. The versatile chiral cycloadducts could be selectively converted into various valuable bridge systems, showing great potential for the construction of natural and bioactive compounds containing a [3.n.1] moiety.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Mariola Zielinska-Blajet, Joanna Najdek
Summary: An efficient approach to synthesizing chiral selenoureas derived from Cinchona alkaloid scaffolds was described in this study. These selenoureas were evaluated as bifunctional organocatalysts in asymmetric Michael addition reactions, with the best results achieved by those containing the 4-fluorophenyl group, showing enantioselectivities up to 96% ee. Additionally, the catalytic performance of thiourea and selenourea counterparts was compared.
Article
Chemistry, Organic
Junwei Zhang, Hao Wu, Weixin Zhang, Liming Wang, Ying Jin
Summary: A series of cinchona alkaloid silyl ether derivatives have been successfully used as catalysts for the enantioselective Friedel-Crafts reaction between indoles and isatins, yielding 3-hydroxy-2-oxindoles with high yields (78% to 96%) and excellent enantioselectivities (up to 99% ee). This methodology has broadened the catalyst type and substrate scope.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Oleg I. Afanasyev, Fedor S. Kliuev, Alexey A. Tsygankov, Yulia V. Nelyubina, Evgenii Gutsul, Valentin V. Novikov, Denis Chusov
Summary: This study demonstrates that the simple in situ addition of fluoride to asymmetric organometallic catalysts can improve both their activity and enantioselectivity. The approach has been successfully applied to prepare several enantioenriched GABA analogues.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Shuting Tan, Jian-Guo Liu, Ming-Hua Xu
Summary: A rhodium-catalyzed asymmetric 1,4-addition reaction provides a practical approach for synthesizing highly enantioenriched chiral N-alkylindoles.
Article
Chemistry, Organic
Shiqiang Wei, Xiaoze Bao, Shah Nawaz, Jingping Qu, Baomin Wang
Summary: A novel tartrate-derived guanidine catalyst was identified through a modular approach for the Michael addition of 3-aminooxindoles to nitroolefins. Quaternary 3-aminooxindoles with adjacent quaternary-tertiary stereocenters were obtained in good to excellent yields (up to 95%) with good to excellent diastereo- and enantioselectivities (up to >20:1 dr and 98% ee).
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Zara M. Seibel, Jeffrey S. Bandar, Tristan H. Lambert
Summary: The enantioselective synthesis of alpha-substituted glutamates and pyroglutamates via a cyclopropenimine-catalyzed Michael addition of amino ester imines has been described, achieving enantioselectivities of up to 94% and compatibility with various functional groups. The impact of catalyst structure and imine substitution was discussed, highlighting a broader and more enantioselective access to pyroglutamate derivatives compared to other methods.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xuqiang Guo, Xuejun Sun, Mengmeng Jiang, Yulei Zhao
Summary: A practical and efficient protocol for the switchable synthesis of sulfoxides, sulfones, and thiosulfonates has been developed, which involves the Selectfluor-mediated oxidation of sulfides and thiols. The reactions proceed rapidly at ambient temperature and yield the desired products with high efficiency.
SYNTHESIS-STUTTGART
(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, Organic
Xi-Yu Wang, Min Yang, Ying Zhou, Jian Zhou, Yong-Jia Hao
Summary: A highly efficient metal-free selective 1,4-addition reaction of difluoroenoxysilanes to chromones was developed using HOTf as the catalyst, providing a facile method to access valuable C2-difluoroalkylated chroman-4-one derivatives. The products could be converted to the difluorinated bioisostere of the natural product (S)-2,6-dimethylchroman-4-one and a difluorinated benzo-seven-membered heterocycle via the Schmidt rearrangement reaction. Compound 3g exhibited potent inhibitory effect on HCT116 cancer cells, making it a promising lead compound for further optimization and evaluation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(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, Physical
Xiao-Yuan Cui, Zhong-Tian Ye, Hai-Hong Wu, Chang-Ge Ji, Feng Zhou, Jian Zhou
Summary: We report on a metal-catalyzed formal intermolecular carbene insertion reaction into the vinylic C(sp(2))-H bond of alkenes, with Au(I) catalyst proving to be the most efficient among the screened metal catalysts. This reaction provides a facile method to access C4-alkenyl isochromanones and isoquinolinones from corresponding diazo reagents and alpha-methylstyrenes, with moderate to good yields, and excellent chemoselectivity. Mechanistic studies suggest the existence of two possible reaction pathways: nucleophilic attack-selective elimination by the gold-carbenoid and cyclopropanation-ring-opening-olefin isomerization process. The structure of the diazo reagents has a significant impact, as diazo(thio)oxindoles react with alpha-methylstyrenes via formal allylic C(sp(3))-H insertion to afford 3-allyl(thio)oxindoles.
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, 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, Organic
Yulei Zhao, Shuai Li, Yuhang Fan, Jun Cao, Xiaotong Dong, Ruiqing Wang, Laijin Tian
Summary: An unprecedented C-sp3-H imination reaction using arylazo sulfones as the readily accessible and stable N source is reported. The synthetic virtues of this reaction include mild conditions, simple operation, good air compatibility, and functional group tolerance, as well as suitability for gram-scale reaction. The resulting imines can be further converted to α-amino acids. The presented results shed light on the unusual usage of arylazo sulfones and will inspire novel experimental design by using arylazo sulfones as the N source.
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, Multidisciplinary
Wen-Hui Zhang, Zi-Yue Chen, Ren-Ming Liu, Xiong-Wei Liu, Bo-Wen Pan, Jian Zhou, Ying Zhou, You-Ping Tian, Xiong-Li Liu
Summary: Herein, previously unreported trimethylindolenines are used as C-N synthons in [3+2] cycloaddition reactions to build a library of spiro[oxindole-thioxoimidazolidine-indoline] hybrids. Catalyst-free conditions lead to smooth formation of a wide range of intriguing and complex products with three pharmacophores and three adjacent quaternary stereocentres, with up to 92% yield and >20 : 1 dr. This strategy expands the diversity of polyheterocycles and aids in the discovery of new bioactive molecules.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Xiong-Wei Liu, Zi-Yue Chen, Ren-Ming Liu, Wen-Hui Zhang, Bo-Wen Pan, Jian Zhou, You-Ping Tian, Ying Zhou, Xiong-Li Liu
Summary: Here, we report the use of previously unreported Fischer's base reactants as useful 2C building blocks in (3+2) cycloaddition reactions to construct a library of bispiro[Fischer's base-oxindole] hybrids. These structurally intriguing products, which contain three adjacent quaternary stereocentres, are obtained smoothly with yields up to 82% and >20:1 dr under catalyst-free conditions. Importantly, this study demonstrates for the first time the use of 3-isothiocyanato oxindole as an acceptor and then as a donor in formal (3+2) cycloadditions, providing a practical and straightforward approach to structurally diverse cycloadducts. This work expands the previously limited applicability scope of 3-isothiocyanato oxindoles, which were mainly used as donor/acceptor-based synthons in cycloadditions.
CHEMICAL COMMUNICATIONS
(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
Jun-Song Tian, Zhi Tu, Feng Zhou, Jin-Sheng Yu, Jian Zhou
Summary: The C=N double bonds are elaborated to provide a facile route for the synthesis of structurally diverse amine derivatives, which play a significant role in drug discovery and development. Although tandem synthesis based on the C-attack addition of nucleophiles to C=N bonds is well-established, there has been limited progress in exploiting sequential tandem reactions starting from imine N-attack nucleophilic addition reactions. In this study, the first one-pot tandem sequences based on an intramolecular ketimine N-attack addition reaction are reported, allowing for the synthesis of N-functionalized indoles, which are difficult to access by other methods, and have potential applications in medical research.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
