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
Steeva Sunny, Mohit Maingle, Kapileswar Seth
Summary: The application of bifunctional organocatalysts, specifically squaramides, in organic chemistry has significantly advanced due to their stability, low toxicity, ease of handling, and recoverability. This review article provides a comprehensive report on the fine-tunable bifunctional chiral squaramide-catalyzed sulfa-Michael addition, emphasizing the construction of complex molecular entities with multiple stereocenters. The article also summarizes the progress made in chiral squaramide-catalyzed asymmetric sulfa-Michael addition and subsequent cascade reactions between 2011 and 2022.
Article
Chemistry, Organic
Oceane Flores, Patrick Wagner, Jean Suffert
Summary: Exploration of 4-exo-dig cyclocarbopalladation in the discovery of new and original scaffolds resulted in unexpected findings, including the identification of polycyclic molecules with a tetrasubstituted carbon. The presence of a triple bond substituting the cyclohexene ring on the starting compound was found to be crucial for high stereoselectivity. This observation was confirmed by the reaction of a nonsubstituted cyclohexene ring, which led to poor stereoselectivity and low yields.
Article
Chemistry, Medicinal
Zhiwei Ma, Chuanchuan Wang, Xiaofeng Liu, Xiaopei Chen, Jingchao Tao, Quanjian Lv
Summary: A newly developed tertiary amine-squaramide organocatalyst has shown excellent performance in the asymmetric Michael addition reaction, achieving high yields and enantioselectivities with low catalyst loading. This catalyst system has the potential for efficient synthesis of coumarin derivatives in organic chemistry applications.
Article
Chemistry, Applied
Yabo Deng, Shuo Sun, Yuqiang Wang, Pengfeng Jia, Wenguang Li, Kairong Wang, Wenjin Yan
Summary: A novel domino reaction has been disclosed utilizing quinidine-derived ammonium salts as a phase transfer catalyst, facilitating the efficient synthesis of a range of CF2H-containing spirofindoline-3,3'-thiophenels under mild conditions. The reaction resulted in high yields, excellent diastereoselectivities, and good enantioselectivities in short reaction times.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
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
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, Organic
Pamela Mackey, Aneta Turlik, Kaori Ando, Mark E. Light, K. N. Houk, Gerard P. McGlacken
Summary: The study demonstrates the stereoselective formation of 5 contiguous chiral centers in a single pot reaction using aldol, aldol-Tishchenko reaction of N-tert-butyl sulfinimines. The researchers synthesized a series of cyclic and acyclic 3-amino-1,5-diol derivatives with high yields and excellent diastereoselectivities. The investigation supports two reversible aldol steps and a remarkably selective, irreversible Tishchenko reduction.
Article
Chemistry, Organic
Jian Xu, Runze Li, Nian Xu, Xiaohua Liu, Fei Wang, Xiaoming Feng
Summary: The study describes the asymmetric catalytic synthesis of 3-cyclotrypt-amine substituted oxindoles with potential anticancer activity. This strategy allows for the quick assembly of cyclotryptamine subunits with two quaternary stereogenic centers in cis-selectivity.
Article
Chemistry, Organic
Jing-Wei Zhou, Ben-Hong Chen, Feng-Hua Zhang, Jing Xue, Xiang-Hong He, Cheng Peng, Wei Huang, Qian Zhao
Summary: This work presents a newly designed strategy for a Michael-initiated ring-closing [3+2] cycloaddition reaction between 3-(1-benzyl-2-oxoindolin-3-yl)pentane-2,4-diones and alpha,beta-unsaturated aldehydes. The reaction, catalyzed by a chiral secondary amine, efficiently produces highly functionalized spirocyclopentane oxindole derivatives with five consecutive stereogenic centers, including two tetrasubstituted carbons. The desired products are obtained with high yields, excellent enantioselectivities, and diastereoselectivities. Furthermore, this strategy demonstrates practicality through gram-scale experiments and a series of synthetic transformations.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Jacob W. Cleveland, Nima Ronaghi, Christopher W. Jones
Summary: The study involved performing a three-step reaction cascade converting benzyl alcohol, sodium hypochlorite and malononitrile to a biologically active derivative with a yield above 80%. By optimizing the reaction conditions through stepwise reagent addition, the researchers successfully demonstrated a simple and effective method for generating mesoporous materials with two types of active sites.
MOLECULAR CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Xin Qin, Jinhai Zhang, Zhan-Yong Wang, Yimei Song, Yixiao Yang, Wenhai Zhang, Hongxin Liu
Summary: In this study, a aldol/Michael cascade reaction on the beta,gamma-positions of alpha,beta-unsaturated ketones with ketoamides to construct bicyclic lactams via DBU catalysis has been developed. The substrates exhibited high regio- and diastereoselectivities and yielded moderate to good results (32 examples). Control experiments showed that the hydrogen of the amide played a key role.
Review
Chemistry, Organic
Soniya Gandhi, Vishnudas Sivadas, Beeraiah Baire
Summary: The research discusses the recent advancements in bifunctional organocatalyst promoted, relay-cascade catalysis, highlighting its potential for green synthesis. The cascade catalysis is categorized into double-, triple-, and quadruple cascades, each involving different combinations of reactions. This strategy has successfully achieved diverse polycyclic structural frameworks, showing promise for further development in greener chemistry approaches.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Abhisek Midya, Laxman Devidas Khalse, Prasanta Ghorai
Summary: In this study, an amine-catalyzed reductive aldol-condensation followed by an intramolecular reductive Michael-addition cascade was demonstrated, using Hantzsch ester as a hydride source to a keto-bis-enone, leading to the synthesis of enantio- and diastereoselective benzannulated diquinanes with three consecutive stereocenters, including an all-carbon quaternary formyl stereocenter. Interestingly, changing the tether from an aliphatic to an aromatic moiety resulted in a change in reactivity, where an asymmetric aldol reaction, followed by an iminium/enamine isomerization and diastereoselective Michael addition reaction, resulted in the formation of a bis-benzannulated diquinane with vicinal congested quaternary chiral centers.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Engineering, Environmental
Hong-Chao Lan, Ya-Ting Zou, Yi-Chao Wang, Ning-Ning Cheng, Wen-Long Xu, Hai-Long Peng, Kuan Huang, Li-Yun Kong, Jun Du
Summary: A new composite sorbent was developed for efficient capture of SO2, showing excellent SO2 adsorption efficiency at extremely low pressures.
CHEMICAL ENGINEERING JOURNAL
(2021)
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, 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, 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, Multidisciplinary
Xiaopeng Fan, Tianbing Ren, Wen Yang, Xiaobing Zhang, Lin Yuan
Summary: A novel dual-modal probe (NO2-CS) was rationally developed and applied for imaging isoniazid-induced liver hypoxia by detecting the over-expressed nitroreductase, which is crucial for the effective monitoring and treatment of drug-induced liver injury.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Xi-Qiang Hou, Ye Lin, Da-Ming Du
Summary: An efficient asymmetric domino annulation method was developed for the enantioselective construction of functionalized bridged fused ring heterocycles bearing three adjacent stereogenic centers in high yields with excellent diastereo- and enantioselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2021)