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Isosteviol-Type Organocatalysts in Asymmetric Catalysis over the Past Decade
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作者 Liu Yuxia Li Congcong +2 位作者 Fan Zhaoyang Liu Qi Dai Xinyu 《有机化学》 北大核心 2025年第10期3613-3623,共11页
Isosteviol,the hydrolysate of stevioside,has attracted increasing attention from scientists because of its special molecular skeleton and extensive biological activities.In recent years,due to the continuous rise of o... Isosteviol,the hydrolysate of stevioside,has attracted increasing attention from scientists because of its special molecular skeleton and extensive biological activities.In recent years,due to the continuous rise of organocatalysis,an increasing number of organocatalysts based on isosteviol have been devised and synthesized to facilitate a range of highly enantioselective asymmetric synthesis.The isosteviol-type organocatalysts reported in the literature over the past decade and their applications in asymmetric catalysis are systematically analyzed and elaborated in order to provide assistance for the further design,synthesis,and application of organocatalysis derived from isosteviol. 展开更多
关键词 asymmetric catalysis ORGANOCATALYST ISOSTEVIOL bifunctional catalyst thiourea SQUARAMIDE
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Michael Addition of Thiols to á, -Unsaturated Carbonyl Compounds Catalyzed by Bifunctional Organocatalysts: Asymmetric Michael Addition and Asymmetric Protonation
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作者 LI Bang-Jing JIANG Lin +2 位作者 LIU Min DING Li-Sheng CHEN Ying-Chun 《合成化学》 CAS CSCD 2004年第z1期48-48,共1页
关键词 Michael addition organocatalysts bifunctional PROTONATION hydrogen-bonding activation
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Enantioselective Aldol Reactions and Michael Additions Using Proline Derivatives as Organocatalysts
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作者 Mathieu Wagner Yohan Contie +1 位作者 Clotilde Ferroud Gilbert Revial 《International Journal of Organic Chemistry》 2014年第1期55-67,共13页
Six compounds including five proline derivatives have been prepared and tested as chiral organocatalysts for enantioselective aldol reactions and Michael additions. The enantiomeric excesses, which are highly dependen... Six compounds including five proline derivatives have been prepared and tested as chiral organocatalysts for enantioselective aldol reactions and Michael additions. The enantiomeric excesses, which are highly dependent on the molecular structure of catalysts as well as experimental conditions, have reached over 98%. 展开更多
关键词 ALDOL Reactions MICHAEL ADDITIONS ENANTIOSELECTIVE organocatalysts PROLINE Derivatives
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A family of novel bifunctional organocatalysts:Highly enantioselective alcoholysis of meso cyclic anhydrides and its application for synthesis of the key intermediate of P2X_7 receptor antagonists 被引量:3
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作者 Hong-Jun Yang Fang-Jun Xiong +1 位作者 Jie Li Fen-Er Chen 《Chinese Chemical Letters》 SCIE CAS CSCD 2013年第7期553-558,共6页
A family of novel squaramides/sulfamides based on 1,2-alkamine was developed as chiral bifunctional catalysts to promote the asymmetric alcoholysis of meso cyclic anhydrides. The hemiesters were obtained in high yield... A family of novel squaramides/sulfamides based on 1,2-alkamine was developed as chiral bifunctional catalysts to promote the asymmetric alcoholysis of meso cyclic anhydrides. The hemiesters were obtained in high yield with up to 93% ee. The usefulness of this methodology was demonstrated in the asymmetric synthesis of the key intermediate of P2X7 receptor antagonists. 展开更多
关键词 Asymmetric alcoholysis Bifunctional organocatalyst Cyclic anhydrides P2X7 receptor antagonists Sulfamides
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Carbohydrate-Derived Organocatalysts for the Reduction of Imines with Trichlorosilane
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作者 Xin Ge Chao Qian Xinzhi Chen 《Journal of Materials Science and Chemical Engineering》 2015年第6期48-53,共6页
The backbone of D-glucosamine hydrochloride was fine-tuned and modified by protecting the hydroxyl groups. In order to reduce imines with trichlorosilane, the carbohydrate-derived organocatalysts were prepared and scr... The backbone of D-glucosamine hydrochloride was fine-tuned and modified by protecting the hydroxyl groups. In order to reduce imines with trichlorosilane, the carbohydrate-derived organocatalysts were prepared and screened. Methyl-4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyr anoside was found as the best catalyst. The reduction was proceeded under CHCl3 as solvent at 40?C, affording 68% - 94% yield. 展开更多
关键词 CARBOHYDRATE ORGANOCATALYST REDUCTION Imine
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Asymmetric Aldol Reaction Catalyzed by Modularly Designed Organocatalysts
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作者 Sinha, Debarshi Mandal, Tanmay Gogoi, Sanjib Goldman, Joshua J. 赵从贵 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2012年第11期2624-2630,共7页
The self-assembly of the precatalyst modules, which are amino acids and cinchona alkaloid derivatives, leads to the direct formation of the desired organocatalysts without any synthesis. These modularly designed organ... The self-assembly of the precatalyst modules, which are amino acids and cinchona alkaloid derivatives, leads to the direct formation of the desired organocatalysts without any synthesis. These modularly designed organocatalysts (MDOs) may be used for catalyzed asymmetric aldol reaction the corresponding aldol products may be obtained in mediocre diastereoselectivities (up to 79 : 21 dr). Depending on structure of the aldehyde substrates, to excellent ee values (up to 92% ee) with moderate 展开更多
关键词 modularly designed organocatalysts aldol reaction asymmetric catalysis amino acid cinchona alka-loid thiourea
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Novel supramolecular organocatalysts of hydroxyprolinamide based on calix[4]arene scaffold for the enantioselective Biginelli reaction 被引量:2
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作者 LI ZhengYi XING HuaiJie +3 位作者 HUANG GuoLi SUN XiaoQiang JIANG JuLi WANG LeYong 《Science China Chemistry》 SCIE EI CAS 2011年第11期1726-1734,共9页
A series of novel supramolecular organocatalysts of hydroxyprolinamide based on the upper rim of calix[4]arene scaffold have been developed to catalyze enantioselective multi-component Biginelli reaction. Under the op... A series of novel supramolecular organocatalysts of hydroxyprolinamide based on the upper rim of calix[4]arene scaffold have been developed to catalyze enantioselective multi-component Biginelli reaction. Under the optimal conditions, the reactions occurred with moderate-to-excellent enantioselectivities (up to 98% ee). A plausible transition state constructed by the supra- molecular interaction of hydrogen bond and cation-π between catalysts and substrates has been proposed. 展开更多
关键词 supramolecular organocatalyst CALIX[4]ARENE hydroxyprolinamide enantioselective Biginelli reaction
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Lewis base-CO2 adducts as organocatalysts for CO2 transformation 被引量:2
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作者 Hui Zhou Xiaobing Lu 《Science China Chemistry》 SCIE EI CAS CSCD 2017年第7期904-911,共8页
In the recent decade, the development and application of organocatalysis for CO_2 transformation into useful chemicals have attracted much attention. Among these organocatalysts, Lewis base-CO_2 adducts(LB-CO_2) were ... In the recent decade, the development and application of organocatalysis for CO_2 transformation into useful chemicals have attracted much attention. Among these organocatalysts, Lewis base-CO_2 adducts(LB-CO_2) were found to be more efficient.The used Lewis base has great effect on the catalytic activity of its CO_2 adduct. This review reports the recent progress in LB-CO_2 adducts catalyzed the cyclization of CO_2 with epoxides or aziridines to afford cyclic carbonates or oxazolidinones,the carboxylation of CO_2 with propargylic alcohols to α-alkylidene cyclic carbonates, and the reduction of CO_2 to methanol,formamides and methylamines, with the focus on the catalytic mechanism. 展开更多
关键词 Lewis base CO2 adduct organocatalyst CO2 transformation cyclic carbonate
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Light-driven site-selective O–H activation in lignin by triplet excited alkylanthraquinone at simulated natural conditions
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作者 Lixia Li Xiuqi Li +5 位作者 Feiyue Li Xiang Zhen Mingdong Dong Jinxing Long Xiaobing Wang Zhiyong Jiang 《Chinese Journal of Catalysis》 2025年第9期65-80,共16页
Harnessing photocatalyzed hydrogen atom transfer(HAT)for the precise activation of C–H/O–H bonds is a pivotal yet challenging strategy to selectively drive oxidative C–C bond scission in renewable lignin,yielding v... Harnessing photocatalyzed hydrogen atom transfer(HAT)for the precise activation of C–H/O–H bonds is a pivotal yet challenging strategy to selectively drive oxidative C–C bond scission in renewable lignin,yielding value-added chemicals with exceptional selectivity.Herein,we present a metal-free photochemical strategy that enables selective C–C bond scission in lignin via a unique synergistic HAT pathway driven by triplet-excited 2-ethylanthraquinone(EAQ^(*))and hydroxyl radicals(•OH)generated in situ from EAQH_(2) and O_(2).Under simulated natural conditions,this process achieves a benzaldehyde yield of 146.6 mol%from a lignin-derived phenolic dimer.Mechanistic investigations reveal that preferential activation of the Cα-OH in lignin facilitates a tandem HAT process,forming alkoxy radical intermediates that undergoβ–scission to produce benzaldehyde,as corroborated by extensive control reactions and density functional theory calculations.Furthermore,this straightforward protocol efficiently cleaves the C–C bonds of technical kraft lignins,providing a rapid,scalable,and metal-free protocol for lignin valorization under mild conditions. 展开更多
关键词 LIGNIN Oxidative degradation Photoredox organocatalyst 2-ETHYLANTHRAQUINONE BENZALDEHYDE
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Bifunctional organocatalyst-catalyzed dynamic kinetic resolution of hemiketals for synthesis of chiral ketals via hydrogen bonding control
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作者 Meng Shan Yongmei Yu +4 位作者 Mengli Sun Shuping Yang Mengqi Wang Bo Zhu Junbiao Chang 《Chinese Chemical Letters》 2025年第1期248-252,共5页
Herein,we report the dynamic kinetic resolution asymmetric acylation ofγ-hydroxy-γ-perfluoroalkyl butenolides/phthalides catalyzed by amino acid-derived bifunctional organocatalysts,and a series of ketals were obtai... Herein,we report the dynamic kinetic resolution asymmetric acylation ofγ-hydroxy-γ-perfluoroalkyl butenolides/phthalides catalyzed by amino acid-derived bifunctional organocatalysts,and a series of ketals were obtained in high yields(up to 95%)and excellent enantioselectivities(up to 99%).In terms of synthetic utility,the reaction can be performed on a gram scale,and the product can be converted into potential biological nucleoside analog. 展开更多
关键词 Bifunctional organocatalyst Dynamic kinetic resolution Hemiketal Chiral ketals Hydrogen bonding
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Recent advances towards catalytic asymmetric Conia-ene-type reactions 被引量:1
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作者 En-Ze Lin Yin Xu +1 位作者 Kegong Ji Long-Wu Ye 《Chinese Chemical Letters》 SCIE CAS CSCD 2021年第3期954-962,共9页
Conia-ene reactions,as a type of ene reactions,have not become a remarkable focus until the beginning of21st century,when Lewis acids served as powerful catalysts and found an increasingly broad utilization in this fi... Conia-ene reactions,as a type of ene reactions,have not become a remarkable focus until the beginning of21st century,when Lewis acids served as powerful catalysts and found an increasingly broad utilization in this field.Consequently,the catalytic Conia-ene reactions have gained great significance in synthetic chemistry due to their high efficiency and atom economy on the construction of valuable cyclic molecules.During the past two decades,the rapid development of transition-metal catalysis and organocatalysis has imposed a profound impact on the exploration of asymmetric Conia-ene reactions.As a result,several strategies have been developed and applied successfully.Organized on the basis of the catalytic system,this review comprehensively presents a summary of recent progress achieved in this emerging domain,aimed at highlighting the reactions’features,practicalities,and the mechanistic rationale is presented where possible. 展开更多
关键词 Conia-ene reaction Asymmetric catalysis Transition metals organocatalysts
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Potassium phthalimide:An efficient and green organocatalyst for the synthesis of 4-aryl-7-(arylmethylene)-3,4,6,7-tetrahydro-1Hcyclopenta[d]pyrimidin-2(5H)-ones/thiones under solvent-free conditions 被引量:3
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作者 Hamzeh Kiyani Maryam Ghiasi 《Chinese Chemical Letters》 SCIE CAS CSCD 2014年第2期313-316,共4页
An efficient synthesis of Biginelli-type compounds using potassium phthalimide as a green, mild, and commercially available organocatalyst in a one-pot, multi-component cyclocondensation reaction of cyclopentanone, al... An efficient synthesis of Biginelli-type compounds using potassium phthalimide as a green, mild, and commercially available organocatalyst in a one-pot, multi-component cyclocondensation reaction of cyclopentanone, aldehydes, and urea/thiourea is reported. The present methodology is a green approach to access 4-aryl-7-(aryImethylene)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-ones/thiones. It offers several merits such as simple operational procedures, no use of hazardous organic solvents, and cheap and environmentally friendly solid basic catalyst. 展开更多
关键词 ORGANOCATALYST Potassium phthalimide Biginelli reaction PyrimidinoneSolvent-free
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Highly efficient and easy synthesis of 2,4,6-triarylpyridines catalyzed by pentafluorophenylammonium triflate(PFPAT) as a new recyclable solid acid catalyst in solvent-free conditions 被引量:2
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作者 Naser Montazeri Saber Mahjoob 《Chinese Chemical Letters》 SCIE CAS CSCD 2012年第4期419-422,共4页
Pentafluorophenylammonium triflate(PFPAT) was found to be a highly efficient catalyst for the preparation of 2,4,6- triarylpyridines from the reaction of acetophenone derivatives,aromatic aldehydes and ammonium acet... Pentafluorophenylammonium triflate(PFPAT) was found to be a highly efficient catalyst for the preparation of 2,4,6- triarylpyridines from the reaction of acetophenone derivatives,aromatic aldehydes and ammonium acetate.Present methodology offers several advantages,such as short reaction time,high yields,simple procedure with an easy work-up and the absence of any volatile and hazardous organic solvent.In addition,this catalytic system can act as an active,inexpensive,metal-free,recoverable and recyclable catalyst. 展开更多
关键词 Pentafluorophenylammonium triflate 2 4 6-Triarylpyridines Solvent-free conditions ORGANOCATALYST Multi-component reaction
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Functionalization of nitrogen-doped graphene quantum dot:A sustainable carbon-based catalyst for the production of cyclic carbonate from epoxide and CO_(2) 被引量:1
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作者 Zahra Eshaghi Gorji Abbas Ali Khodadadi +3 位作者 Siavash Riahi Timo Repo Yadollah Mortazavi Marianna Kemell 《Journal of Environmental Sciences》 SCIE EI CAS CSCD 2023年第4期408-422,共15页
A series of organic compounds were successfully immobilized on an N-doped graphene quantum dot (N-GQD) to prepare a multifunctional organocatalyst for coupling reaction between CO_(2)and propylene oxide (PO).The simul... A series of organic compounds were successfully immobilized on an N-doped graphene quantum dot (N-GQD) to prepare a multifunctional organocatalyst for coupling reaction between CO_(2)and propylene oxide (PO).The simultaneous presence of halide ions in conjunction with acidic-and basic-functional groups on the surface of the nanoparticles makes them highly active for the production of propylene carbonate (PC).The effects of variables such as catalyst loading,reaction temperature,and structure of substituents are discussed.The proposed catalysts were characterized by different techniques,including Fourier transform infrared spectroscopy (FTIR),field emission scanning electron microscopy/energy dispersive X-ray microanalysis (FESEM/EDX),thermogravimetric analysis (TGA),elemental analysis,atomic force microscopy (AFM),and ultraviolet–visible (UV-Vis) spectroscopy.Under optimal reaction conditions,3-bromopropionic acid (BPA) immobilized on N-GQD showed a remarkable activity,affording the highest yield of 98%at 140℃ and 106Pa without any co-catalyst or solvent.These new metal-free catalysts have the advantage of easy separation and reuse several times.Based on the experimental data,a plausible reaction mechanism is suggested,where the hydrogen bonding donors and halogen ion can activate the epoxide,and amine functional groups play a vital role in CO_(2)adsorption. 展开更多
关键词 Heterogeneous organocatalyst CO_(2) Propylene carbonate N-doped graphene quantum dot Nanomaterials
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One-step,synthesis of Hantzsch esters and polyhydroquinoline derivatives using new organocatalyst 被引量:1
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作者 Seyed Meysam Baghbanian Samad Khaksar +2 位作者 Seyed Mohammad Vahdat Maryam Farhang Mahmood Tajbakhsh 《Chinese Chemical Letters》 SCIE CAS CSCD 2010年第5期563-567,共5页
Herein we report an efficient organocatalyst for the multicomponent Hantzsch reaction under mild condition.The product easily isolated by simple filtration and catalyst can be recovered.
关键词 ORGANOCATALYST Four-component coupling reactions POLYHYDROQUINOLINE
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Organocatalytic enantioselective construction of bicyclic γ-butrolactones
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作者 Qiang Zhang Jingxiang Pang +7 位作者 Tian-Zhang Wang Feng Chen Minghao Shen Tianyu Li Yongshuai Chai Yu-Feng Liang Jie Sun Zhushuang Bai 《Chinese Chemical Letters》 SCIE CAS CSCD 2023年第7期122-126,共5页
An enantioselective organo-catalyzed reaction of furanones with α,β-unsaturated ketones has been established herein, which provides an efficient access to chiral bicyclic γ-butyrolactones in good yields, enantiosel... An enantioselective organo-catalyzed reaction of furanones with α,β-unsaturated ketones has been established herein, which provides an efficient access to chiral bicyclic γ-butyrolactones in good yields, enantioselectivities and diastereoselectivities. Further transformations of product are demonstrated. A diamine mediated catalytic cycle is proposed. 展开更多
关键词 ORGANOCATALYST Asymmetric synthesis Bicyclicγ-butyrolactone DIAMINE CYCLIZATION
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Imidazol-1-yl-acetic acid as a novel green bifunctional organocatalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions
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作者 Simin Nazari Mosadegh Keshavarz +2 位作者 Bahador Karami Nasir Iravani Masoumeh Vafaee-Nezhad 《Chinese Chemical Letters》 SCIE CAS CSCD 2014年第2期317-320,共4页
Imidazol-1-yl-acetic acid is introduced as a new, efficient and recyclable green bifunctional organocatalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions. This catalyst is water solub... Imidazol-1-yl-acetic acid is introduced as a new, efficient and recyclable green bifunctional organocatalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions. This catalyst is water soluble and can be separated from the products by simple filtration. The filtrate can be evaporated to dryness and recrystallized from cool methanol to give the recovered catalyst. This organocatalyst was used for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-flee conditions and recycled up to 8 consecutive runs without any losing of its efficiency. 展开更多
关键词 Bifunctional catalyst ORGANOCATALYST SOLVENT-FREE 1 3-Dicarbonyl compounds 1 8-Dioxooctahydroxanthenes
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新型五氟苯铵三氟有机催化剂高效合成14-芳基(烷基)-14H-二苯并[a,j]呫吨类化合物和1,8-二氧代氧杂蒽衍生物(英文)
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作者 Samad KHAKSAR Nosratollah BEHZADI 《催化学报》 SCIE EI CAS CSCD 北大核心 2012年第6期982-985,共4页
A simple and facile synthesis of 14-aryl and alkyl-14H-dibenzo[a,j]xanthenes and 1,8-dioxooctahydroxanthene derivatives has been successfully developed by treatment of β-naphthol or dimedone with aldehydes under mild... A simple and facile synthesis of 14-aryl and alkyl-14H-dibenzo[a,j]xanthenes and 1,8-dioxooctahydroxanthene derivatives has been successfully developed by treatment of β-naphthol or dimedone with aldehydes under mild conditions in the presence of a pentafluorophenyl ammonium triflate(PFPAT) organocatalyst.These catalytic condensation reactions represent green chemical processes and the PFPAT organocatalyst is air-stable,cost-effective,easy to handle,and easily removed from the reaction mixtures. 展开更多
关键词 pentafluorophenyl ammonium triflate ORGANOCATALYST XANTHENE Β-NAPHTHOL
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Recent advances in gold-complex and chiral organocatalyst cooperative catalysis for asymmetric alkyne functionalization
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作者 Ming Bao Su Zhou +1 位作者 Wenhao Hu Xinfang Xu 《Chinese Chemical Letters》 SCIE CAS CSCD 2022年第12期4969-4979,共11页
Homogeneous gold catalysis has demonstrated the preponderant capability of realizing a broad range of synthetically versatile alkyne functionalization over the last two decades.Though catalytic asymmetric alkyne trans... Homogeneous gold catalysis has demonstrated the preponderant capability of realizing a broad range of synthetically versatile alkyne functionalization over the last two decades.Though catalytic asymmetric alkyne transformation has focused on the principle of using gold catalysts either associated with chiral phosphine ligand or combined with chiral counterion,a variety of breakthroughs have been reported with the application of gold-complex and chiral organocatalyst cooperative catalysis strategy,which could enable the challenging transformations that cannot be realized by mono-catalysis with excellent stereoselectivity.This review will cover two general protocols in this field,including relay catalysis and synergistic catalysis,with emphasis on the detailed cooperative catalysts models to illustrate the roles of the two catalysts and highlight the potential synthetic opportunities offered by asymmetric cooperative catalysis. 展开更多
关键词 Gold catalysis Chiral organocatalyst catalysis Relay catalysis Synergistic catalysis Asymmetric alkyne functionalization
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An efficient,recoverable fluorous organocatalyst for accelerating the DABCO-promoted Morita-Baylis-Hillman reaction
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作者 Yi Bo Huang Wen Bin Yi Chun Cai 《Chinese Chemical Letters》 SCIE CAS CSCD 2011年第9期1055-1058,共4页
A convenient method for Morita-Baylis-Hillman reaction of arylaldehydes with methyl acrylate has been developed by using fluorous-tag organocatalyst 1-[4-(perfluorooctyl)phenyl]-3-phenylthiourea and DABCO at room te... A convenient method for Morita-Baylis-Hillman reaction of arylaldehydes with methyl acrylate has been developed by using fluorous-tag organocatalyst 1-[4-(perfluorooctyl)phenyl]-3-phenylthiourea and DABCO at room temperature. The fluorous organocatalyst could be recovered from the reaction mixture by fluorous solid-phase extraction (F-SPE) with excellent purity for direct reuse. 展开更多
关键词 ORGANOCATALYST Morita-Baylis-Hillman reaction Fluorous solid phase extraction (F-SPE)
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