Article
Chemistry, Medicinal
Alime Ebru Aydin, Selda Culha
Summary: The synthesis of chiral squaramide catalysts (8-15) and their catalytic efficiency in the enantioselective conjugate addition of pyrazolones to nitroalkenes were described, providing excellent chemical yields (up to 93%) of chiral 5-methyl-4-(2-nitro-1-arylethyl)pyrazol-3-ol derivatives with high enantioselectivities (up to 97% ee).
Article
Chemistry, Organic
Ye Zhang, Jingcheng Guo, Jinna Han, Xiangui Zhou, Wei Cao, Zhenqian Fu
Summary: The bifunctional squaramide-catalyzed nucleophilic addition of thiophenols to easily available beta-silyl alpha,beta-unsaturated carbonyl compounds has been successfully developed, leading to the efficient preparation of a structurally diverse set of chiral alpha-mercaptosilanes with good to excellent yields and acceptable enantioselectivities. The reaction features mild reaction conditions, a broad substrate scope, and easy scale-up.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
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
Biochemistry & Molecular Biology
Xiao-Yan Dong, Da-Ming Du
Summary: This paper investigated the organocatalytic asymmetric 1,4-Michael addition reaction of azadienes and alpha-thiocyanoindanones, successfully synthesizing a series of chiral thiocyano compounds. By describing a possible reaction mechanism, it broadens the scope of application of azadiene substrates.
Article
Chemistry, Organic
Tarun Kumar Roy, Sachin S. Gorad, Prasanta Ghorai
Summary: An efficient enantio- and diastereoselective spiroketalization method of aromatic ketone tethered to ortho-homoformyl and enone moiety via in situ enol formation using quinine derived squaramide organocatalyst is disclosed. This method provides access to aromatic [6,5] spiroketals with complete atom economy. Furthermore, the aromatic spiroketals can undergo Bronsted acid catalyzed Piancatelli type rearrangement to afford dihydronaphtho[1,2-b]furans with retention of enantioselectivities.
Article
Chemistry, Multidisciplinary
Zhao Han, Jiaping Jin, Alemayehu Gashaw Woldegiorgis, Xufeng Lin
Summary: An efficient organocatalytic method has been developed for the synthesis of enantioenriched triflouromethylated indolin-2-ones bearing adjacent tertiary chiral centers. The use of a newly developed chiral spirobiindane-derived squaramide catalyst is essential in achieving high diastereo- and enantioselectivities.
Article
Chemistry, Organic
Zhi-Wei Ma, Xiao-Feng Liu, Xiao-Pei Chen, Chuan-Chuan Wang, Jing-Chao Tao, Quan-Jian Lv
Summary: A new tertiary amine-thiourea organocatalyst has been developed and applied for the asymmetric Michael addition of pyrazolin-5-one to nitroalkenes. The catalyst system showed excellent performance with a low catalyst loading under mild reaction conditions, leading to the synthesis of chiral pyrazolone derivatives in high yields and good enantioselectivities.
LETTERS IN ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Peng Zhu, Yi Yang, Yan Liu, Yungui Peng
Summary: A series of trifunctional BINAP-based monophosphonium phase-transfer catalysts were developed and used for the asymmetric addition of alpha-diazomethylphosphonates. The method showed high tolerance for 2-unsubstituted sulfonylindoles and achieved high enantioselectivity.
Article
Chemistry, Organic
Jixin Pian, Qingqing Chen, Yujiao Luo, Zhifei Zhao, Jichang Liu, Lin He, Shi-Wu Li
Summary: An enantioselective cyclopropanation reaction of sulfoxonium ylides with beta,gamma-unsaturated ketoesters catalyzed by a chiral rhodium catalyst has been achieved, leading to the synthesis of various optically pure cyclopropanes.
Article
Chemistry, Multidisciplinary
Li Lin, Mei Wang, Jiawei Zhou, Fei Li, Huiyun Liu
Summary: The direct C2 addition of 5H-oxazol-4-ones to gamma-keto-alpha,beta-unsaturated esters catalyzed by a chiral squaramide has been achieved, resulting in diverse highly functionalized gamma-keto esters with a C2-oxazolone at the alpha-position in high yields and excellent stereoselectivities (d.r. > 20:1 and up to 98% ee).
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Zhiwei Ma, Xiaopei Chen, Chuanchuan Wang, Jianling Wang, Jingchao Tao, Quanjian Lu
Summary: A stereoselective methodology has been developed to construct synthetically and pharmaceutically useful chiral chromene derivatives with high yields and enantioselectivities.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Shinji Kitagaki, Eriko Shimo, Sawa Takeda, Rintaro Fukai, Naohiro Kojima, Shun Yoshioka, Naoko Takenaga, Keisuke Yoshida
Summary: The study demonstrated the use of [2.2]paracyclophane as a chiral organocatalyst backbone in the Michael addition reaction of nitroethane to nitrostyrenes. The catalyst based on planar chiral pseudo-ortho-[2.2]paracyclophane produced the desired 1,3-dinitro compounds with high yields and high diastereo- and enantioselectivities.
Article
Chemistry, Organic
Zhi-Wei Ma, Chuan-Chuan Wang, Xiao-Pei Chen, Ai-Qin Li, Jing-Chao Tao, Quan-Jian Lv
Summary: A new organocatalyst system has been developed for the asymmetric Michael addition of cyclic diketones to beta,gamma-unsaturated alpha-keto esters. The system showed high efficiency with low catalyst loading and mild reaction conditions, resulting in the synthesis of chiral bicyclic compounds with high yields and excellent enantioselectivities.
SYNTHESIS-STUTTGART
(2022)
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, Multidisciplinary
Aabid A. Wani, Kriti Mehta, Rajeswara Reddy, Prasad V. Bharatam
Summary: This article reports the 1,1-diaminoazine-catalysed Michael addition reaction of malonates with nitro-olefins. The bifunctional nature of the catalyst facilitates the C-C bond formation.
NEW JOURNAL OF CHEMISTRY
(2023)
Review
Chemistry, Applied
Yong-Xing Song, Da-Ming Du
Summary: The aza-Michael addition cascade reaction is an important synthetic method for constructing functionalized C-N bonds, widely used in the synthesis of chiral drugs, intermediates, and natural products. This review highlights recent developments in asymmetric synthesis, including various types of aza-Michael addition triggered cascade reactions, reaction mechanisms, and derivatization experiments.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Analytical
Xiao-Peng Fan, Wen Yang, Tian-Bing Ren, Shuai Xu, Xiang-Yang Gong, Xiao-Bing Zhang, Lin Yuan
Summary: In this study, an amphiphilic molecular probe was developed for in situ imaging of drug-induced liver injury. The probe showed selectivity and sensitivity towards the target compound and could be used to assess liver injury and analyze the therapeutic efficacy of hepatoprotective medicines.
ANALYTICAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Jiang-Song Zhai, Da-Ming Du
Summary: A bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reaction has been developed to synthesize chiral dispiro[indene-pyrrolidine-pyrimidine] compounds from 2-isothiocyanato-1-indanones and barbiturate-based olefins. The reaction has shown excellent yields and stereoselectivities. The synthetic utility of the products has been demonstrated through gram-scale synthesis, one-pot three-component reactions, and further transformation experiments.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Cheng Niu, Da-Ming Du
Summary: An efficient and practical organocatalytic asymmetric strategy was developed using unsaturated benzothiophenones and alpha-nitroketones catalyzed by bifunctional squaramide via Michael addition and acyl transfer steps, leading to a broad range of chiral acyloxybenzothiophene derivatives with high yields and excellent enantioselectivities. Furthermore, employing different chiral squaramide catalysts and unsaturated benzothiophenones can deliver the acyloxy unit at different positions on the benzothiophene ring.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Tong-Hao Li, Da-Ming Du
Summary: A highly efficient squaramide-catalysed asymmetric domino Michael/Mannich [3 + 2] cycloaddition synthesis method was used to obtain a new class of complex and diverse-skeleton isoxazole compounds with good yields and excellent diastereoselectivities and enantioselectivities. The potential applications of this method were demonstrated through gram-scale synthesis and further transformation experiments.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Qian Shang, Haifang Tang, Yongping Liu, Mingming Yin, Lebin Su, Shimin Xie, Lixin Liu, Wen Yang, Yi Chen, Jianyu Dong, Yongbo Zhou, Shuang-Feng Yin
Summary: The selective condensation/bicycloaromatization of two different arylalkynes was achieved under ligand-free copper (I) catalysis, allowing for the direct synthesis of C-N axial biaryl compounds in high yields with excellent selectivity and functional group tolerance. The use of Cu (I) catalyst and HFIP played critical roles in suppressing undesired reactions and constructing coupled five-six aromatic rings through the selective formation of C(sp(2))-N(sp(2)) bonds and C(sp(2))-C(sp(2)) bonds. This unique reaction has the potential to lead to the simplest asymmetric synthesis of atropoisomeric biaryls, with promising applications in various fields such as biology and pharmaceuticals.
Article
Chemistry, Organic
Jie Li, Xinhui Zhang, Yisen Yao, Yapei Gao, Wen Yang, Wanxiang Zhao
Summary: An efficient palladium-catalyzed Suzuki-Miyaura cross-coupling reaction has been developed for the synthesis of oxygen atom-substituted allylboronates with aryl/vinyl bromides, iodides, and triflates. This protocol offers a broad substrate scope, excellent functional group tolerance, and easy gram-scale preparation, providing an alternative approach for the synthesis of allylic alcohols and their derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Cheng Niu, Da-Ming Du
Summary: A new protocol for accessing CF3-containing bispiro[isoquinolone-pyrrolidine-benzothiophenone]s has been described. A series of 1,3-dipoles were synthesized from isoquinolinetrione and CF3CH2NH2, and the 1,3-dipolar cycloaddition of isoquinolinedione trifluoroethyl ketimines and unsaturated benzothiophenones in the presence of 10 mol% DABCO delivered the corresponding adducts with excellent yields (up to 98%) and diastereoselectivities (up to >20 : 1 dr).
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
Jiang-Song Zhai, Dong-Hua Xie, Da-Ming Du
Summary: A new synthetic method has been developed for the synthesis of chiral bispirocyclic indanone compounds through squaramide-catalyzed asymmetric Michael/cyclization tandem reaction. The obtained products were further transformed through oxidation and methylation reactions.
Review
Chemistry, Multidisciplinary
Cheng Niu, Da-Ming Du
Summary: This review highlights the recent advancements in sulfa-Michael addition-triggered cascade reactions for the stereoselective synthesis of sulfur-containing compounds. It discusses various types of reactions, including sulfa-Michael/aldol, sulfa-Michael/Henry, sulfa-Michael/Michael, sulfa-Michael/Mannich and some sulfa-Michael triggered multi-step processes. The review also introduces reaction mechanisms and derivatization experiments.
Article
Chemistry, Organic
Chenchen Li, Qi Qin, Aocong Guan, Wen Yang, Wanxiang Zhao
Summary: We present a general and efficient transition-metal-free C-C bond cross-coupling reaction of (hetero)-aryl ethers and diarylmethanes via C-(sp(2))-O bond cleavage. The coupling reactions mediated by KHMDS demonstrated high efficiency, broad substrate scope, and good functional group tolerance. The robustness and practicality of this protocol were further demonstrated by gram-scale preparation and diversified product derivatization.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Cheng Niu, Dong-Hua Xie, Da-Ming Du
Summary: An isothiourea-catalysed asymmetric Michael/lactamization cascade reaction of 2-aminobenzothiophenes and alpha,beta-unsaturated anhydrides was developed for the first time, yielding various benzothienopyridinones in good to excellent yields with excellent enantioselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Tong-Hao Li, Cheng Niu, Da-Ming Du
Summary: In this study, a class of o-sulfonylaminostyryl isoxazole synthons were designed for their potential application in asymmetric cascade reactions. The resulting products, structurally complex isoxazole-containing spirooxindole tetrahydroquinolines with three contiguous stereocenters, exhibited high yields, excellent diastereoselectivity, and enantioselectivity, suggesting the synthetic strategy has promising synthetic applications.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Yu Wang, Cheng Niu, Dong-Hua Xie, Da-Ming Du
Summary: This strategy for the stereoselective synthesis of spiro isoxazolone-cyclohexenimines involves a bifunctional squaramide-catalysed vinylogous Michael addition/cyclization cascade reaction. The process is atom-economical, can proceed smoothly under extremely low catalyst loading and mild conditions, and the products have shown moderate to good yields and enantioselectivities. Furthermore, scale-up reaction and product transformation have also been demonstrated.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
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)
