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Recent advances in asymmetric reactions catalyzed by chiral phosphoric acids 被引量:7
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作者 Xin Li Qiuling Song 《Chinese Chemical Letters》 SCIE CAS CSCD 2018年第8期1181-1192,共12页
This review summarizes the very recent advances in asymmetric reactions catalyzed by chiral phosphoric acids(CPAs), a family of versatile catalysts that catalyze a broad range of reactions to afford diverse chiral m... This review summarizes the very recent advances in asymmetric reactions catalyzed by chiral phosphoric acids(CPAs), a family of versatile catalysts that catalyze a broad range of reactions to afford diverse chiral molecules. In the past years, different kinds of chiral phosphoric acids have been designed and developed into a privileged class of catalysts in asymmetric synthesis. A number of remarkable achievements have been made by many groups around the world. Due to length limitation, this review only summarizes those works published from January 2016 to November 2017. Meanwhile, catalytic systems which combine metal catalysts and chiral phosphoric acids will not be discussed in this review. 展开更多
关键词 Chiral phosphoric acids asymmetric reactions ORGANOCATALYSIS Conjugate addition CYCLOADDITION Mannich reaction Friedel–Crafts reactions
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A New Approach to the Asymmetric Reaction of the Chiron 5-L-Menthyloxy-2(5H)-furanones with Horner-Emmons Reagent 被引量:2
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作者 李学强 王凤荣 +1 位作者 何兰 陈庆华 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2003年第7期805-810,共6页
The asymmetric reaction of the chiron 2(5H)-furanones (4a-4c) with the Homer-Emmons reagents (5a-5b) has been investigated. The newly chiral organophosphorus derivatives 6 and 7 were obtained using the phosphoryl-stab... The asymmetric reaction of the chiron 2(5H)-furanones (4a-4c) with the Homer-Emmons reagents (5a-5b) has been investigated. The newly chiral organophosphorus derivatives 6 and 7 were obtained using the phosphoryl-stabilized carbanion as a building block in DMSO under mild conditions. Through the asymmetric introduction, the Horner-Emmons reagent could be transformed to a chiral building block to afford the novel functionalized phosphorus derivatives. The structures of the synthesized compounds 6 and 7 were identified on the basis of their elementary and spectroscopic data, such as IR, 1H NMR, 13C NMR, MS and X-ray crystallography. These results provided a valuable approach to the synthesis of potentially interesting chiral organophosphorus derivatives and probing their biological activities. 展开更多
关键词 chiron 2(5H)-furanones asymmetric reaction Horner-Emmons reagent building block chiral organophosphorus derivative biological activity X-ray crystallography
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Asymmetric Reformatsky Reaction Induced by Dipeptides
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作者 Wang, ZY Shen, J +1 位作者 Jiang, CS You, TP 《Chinese Chemical Letters》 SCIE CAS CSCD 2000年第8期659-662,共4页
For the first time, synthetic dipeptides were applied to the catalysis of asymmetric Reformatsky reaction. Review in this domain & factors influencing enantioselectivity were discussed.
关键词 dipeptide derivative chiral ligands CATALYSIS asymmetric Reformatsky reaction
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Direct asymmetric aldol reaction using MBHA resin-supported peptide containing L-proline unit
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作者 Liang Zhang Wen Bo Ding Yong Ping Yu Hong Bin Zou 《Chinese Chemical Letters》 SCIE CAS CSCD 2009年第9期1065-1067,共3页
MBHA resin-supported tripeptide catalyst system containing L-proline unit has been developed for use in the direct asymmetric aldol reaction of acetone and aldehydes, which afford the corresponding products with satis... MBHA resin-supported tripeptide catalyst system containing L-proline unit has been developed for use in the direct asymmetric aldol reaction of acetone and aldehydes, which afford the corresponding products with satisfactory isolated yields and enantiomeric excesses. 2009 Hong Bin Zou. Published by E]sevier B.V. on behalf of Chinese Chemical Society. All rights reserved. 展开更多
关键词 Direct asymmetric aldol reaction MBHA resin-supported peptide L-PROLINE "Tea-bag" methodology
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Asymmetric Baylis-Hillman Reaction between Chiral Activated Alkenes and Aromatic Aldehydes in Me_(3)N/H_(2)O/Solvent Medium
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作者 Ke HE Zheng Hong ZHOU Hong Ying TANG Guo Feng ZHAO Chu Chi TANG 《Chinese Chemical Letters》 SCIE CAS CSCD 2005年第11期1427-1430,共4页
Chiral activated alkene, L-menthyl acrylate and (+)-N-α-phenylethyl acrylamide, induced asymmetric Baylis-HiUman reaction of aromatic aldehydes was realized at 25℃ for 7 days in Me3N/H2O/solvent homogeneous mediu... Chiral activated alkene, L-menthyl acrylate and (+)-N-α-phenylethyl acrylamide, induced asymmetric Baylis-HiUman reaction of aromatic aldehydes was realized at 25℃ for 7 days in Me3N/H2O/solvent homogeneous medium. The corresponding Baylis-Hillman adducts were obtained in good chemical yield with moderate to excellent diastereoselectivity (up to 99% de). 展开更多
关键词 Chiral activated alkene asymmetric Baylis-Hillman reaction aromatic aldehyde diastereoselectivity
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Synthesis of 7,7’-Disubstituted BINAP and Their Application in Asymmetric Catalytic Reaction
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作者 Jiang Yao-Zhong Yuan Wei-Cheng +2 位作者 Liu Hua Mi Ai-Qiao Gong Liu-Zhu 《合成化学》 CAS CSCD 2004年第z1期32-32,共1页
关键词 diphosphine ligand asymmetric catalytic reaction enantioselectivity.
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Asymmetric Diels-Alder Reaction of 1-(S_R)-p-Tolylsulfinyl-3-penten-2-one with Cyclopentadiene Catalzed by a Chiral Titanium Reagent
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作者 Wen PEI(Department of Chemistry, Yanbian University, Yanji, 133002)Eiji WADA and Shuji KANEMASA (Institute of Advanced Material study, Kyushu University, Kasugakoen, Kasuga 816, Japan) 《Chinese Chemical Letters》 SCIE CAS CSCD 1997年第11期935-936,共2页
Double asymmetric Diels-Alder reaction of 1(SR)-p-Tolylsulfinyl-3-penten-2-one with cyclopentadiene using a chiral titanium reagent was performed. The diastereoselectivity dependent on the size of aryl substituent i... Double asymmetric Diels-Alder reaction of 1(SR)-p-Tolylsulfinyl-3-penten-2-one with cyclopentadiene using a chiral titanium reagent was performed. The diastereoselectivity dependent on the size of aryl substituent involved in the chiral ligands was discussed Absolute configuration of the cycloadducts was conformed. Dramatic reversal of selectivity is observed. 展开更多
关键词 p-Tolylsulfinyl-3-penten-2-one with Cyclopentadiene Catalzed by a Chiral Titanium Reagent S_R asymmetric Diels-Alder reaction of 1
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ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTION BY A CHIRAL SOURCE,5-(1-MENTHYLOXY)-2(5-H)-FURANONE
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作者 Qing Hua CHEN Rei Qi SHU Department of Chemistry,Beijing Normal University,Beijing 100875 《Chinese Chemical Letters》 SCIE CAS CSCD 1990年第1期45-46,共2页
5-(1-Menthyloxy)-2(5-H)-furanone is used as s chiral dipolarophile for thermal asymmetric 1,3-dipolar cycloaddition reaction with C-phenyl-N-phenyl nitrone to give the diastereomerically pure cycloaddition product.
关键词 DATA PPM FURANONE MENTHYLOXY asymmetric 1 3-DIPOLAR CYCLOADDITION reaction BY A CHIRAL SOURCE 5
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Asymmetric PCR method in generation of HBV ssDNA for pyrosequencing 被引量:1
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作者 Nian-cai Peng, Chun-lin Wang, Li-li Zhang, Mao-lin Lu, Zhen-xi Zhang Institute of Biomedical Analytical Technology and Instrumentation, School of Life Science and Technology, Xi’an Jiaotong University, Xi’an 710049, China. 《Journal of Pharmaceutical Analysis》 SCIE CAS 2009年第1期54-56,共3页
Objective To explore the optimal primer ratio and concentration of asymmetric polymerase chain reaction (A-PCR) in producing hepatitis B virus (HBV) single-stranded DNA (ssDNA) for pyrosequencing. Methods A-PCR was ca... Objective To explore the optimal primer ratio and concentration of asymmetric polymerase chain reaction (A-PCR) in producing hepatitis B virus (HBV) single-stranded DNA (ssDNA) for pyrosequencing. Methods A-PCR was carried out to generate HBV ssDNA with forward to reverse primers of different ratios (50∶1, 100∶1) and concentrations (13.0 pmol/25μL and 0.14 pmol/25μL, 19.5 pmol/25μL and 0.21 pmol/25μL), and the product yield and quality were compared respectively. Results The forward to reverse primer ratio of 50∶1 provided better yield and concentration of 19.5 pmol/25μL and 0.21 pmol//25μL generated a clearer band. Conclusion A simple and feasible method to produce HBV ssDNA for pyrosequencing in batch is established. 展开更多
关键词 PYROSEQUENCING asymmetric polymerase chain reaction (A-PCR) hepatitis B virus (HBV) optimization single-stranded DNA
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Rhodium/Ming-Phos-catalyzed asymmetric annulation reaction of silacyclobutanes with terminal alkynes
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作者 Yue Sun Kaida Zhou +2 位作者 Chun Ma Zhiming Li Junliang Zhang 《Green Synthesis and Catalysis》 2024年第3期205-210,共6页
Asymmetric ring-expansion reactions of silacyclobutanes(SCBs)with alkynes have evolved as one of the powerful protocols for the construction of silicon-stereogenic compounds.However,the achievement of highly enantiose... Asymmetric ring-expansion reactions of silacyclobutanes(SCBs)with alkynes have evolved as one of the powerful protocols for the construction of silicon-stereogenic compounds.However,the achievement of highly enantioselective annulation of SCBs with terminal alkynes remains a challenge.Herein,we report a rhodium-catalyzed asymmetric annulation reaction of SCBs with terminal alkynes,which relies on the newly identified chiral sulfinamide phosphine ligand Ming-Phos.This catalytic system exhibits unique effects under mild conditions,leading to the direct synthesis of structurally diverse chiral silacycles in moderate to good yields with high enantioselectivities(up to 95%ee). 展开更多
关键词 Rhodium-catalysis asymmetric annulation reaction Silicon-stereogenic Silacyclobutanes Terminal alkynes
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Carbene-catalyzed activation of cyclopropylcarbaldehydes for mannich reaction andδ-lactam formation:remote enantioselecitvity control and dynamic kinetic asymmetric transformation 被引量:1
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作者 Jie Lv Jun Xu +2 位作者 Xuling Pan Zhichao Jin Yonggui Robin Chi 《Science China Chemistry》 SCIE EI CSCD 2021年第6期985-990,共6页
An N-heterocyclic carbene(NHC)-catalyzed enantioselective Mannich reaction of the remoteγ-carbon of cyclopropylcarbaldehydes is disclosed for the first time.Diastereo-and enantiomerically enriched multicyclicδ-lacta... An N-heterocyclic carbene(NHC)-catalyzed enantioselective Mannich reaction of the remoteγ-carbon of cyclopropylcarbaldehydes is disclosed for the first time.Diastereo-and enantiomerically enriched multicyclicδ-lactam compound is afforded as the main product from 8 possible stereo-specific isomers through dynamic kinetic asymmetric transformation(DYKAT)processes.Multiple chiral functional molecules can be afforded from the lactam products through simple protocols with retentions of the optical purities. 展开更多
关键词 N-heterocyclic carbene ORGANOCATALYSIS dynamic kinetic asymmetric transformation 1-cyclopropylcarbaldehydes asymmetric reactions
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Precise Detection,Control and Synthesis of Chiral Compounds at Single‑Molecule Resolution
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作者 Chen Yang Weilin Hu Xuefeng Guo 《Nano-Micro Letters》 SCIE EI CAS CSCD 2023年第11期400-417,共18页
Chirality,as the symmetric breaking of molecules,plays an essential role in physical,chemical and especially biological processes,which highlights the accurate distinction among heterochiralities as well as the precis... Chirality,as the symmetric breaking of molecules,plays an essential role in physical,chemical and especially biological processes,which highlights the accurate distinction among heterochiralities as well as the precise preparation for homochirality.To this end,the well-designed structure-specific recognizer and catalysis reactor are necessitated,respectively.However,each kind of target molecules requires a custom-made chiral partner and the dynamic disorder of spatial-orientation distribution of molecules at the ensemble level leads to an inefficient protocol.In this perspective article,we developed a universal strategy capable of realizing the chirality detection and control by the external symmetry breaking based on the alignment of the molecular frame to external stimuli.Specifically,in combination with the discussion about the relationship among the chirality(molecule),spin(electron)and polarization(photon),i.e.,the three natural symmetry breaking,single-molecule junctions were proposed to achieve a single-molecule/event-resolved detection and synthesis.The fixation of the molecular orientation and the CMOS-compatibility provide an efficient interface to achieve the external input of symmetry breaking.This perspective is believed to offer more efficient applications in accurate chirality detection and precise asymmetric synthesis via the close collaboration of chemists,physicists,materials scientists,and engineers. 展开更多
关键词 Single-molecule junction Molecular chirality Photonic polarization Electronic spin asymmetric reaction
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One-pot-synthesis of novel cinchonine-based phosphites
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作者 Qiao Feng Wang Xue Ying Liu Xiang Yang Qin Xiao Ye Li Sheng Yong Zhang 《Chinese Chemical Letters》 SCIE CAS CSCD 2009年第7期797-799,共3页
Cinchonine was employed as backbone for the synthesis of novel phosphite compounds with diol substituents. These monophosphinites were provided in one pot with the yields ranged from 63% to 75%. Their structures were ... Cinchonine was employed as backbone for the synthesis of novel phosphite compounds with diol substituents. These monophosphinites were provided in one pot with the yields ranged from 63% to 75%. Their structures were confirmed by NMR spectroscopy and HRMS. C 2009 Sheng Yong Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. 展开更多
关键词 Cinchona alkaloids DIOLS Chiral phosphite asymmetric reaction LIGAND
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Catalytic Enantioselective Methanolysis of 4 -substituted-2-phenyl-5(4H)-oxazolones by Cinchonine
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作者 Xie, LJ Hua, WT 《Chinese Chemical Letters》 SCIE CAS CSCD 1998年第7期605-606,共2页
Cinchonine alkaloid catalyzed enantioselective methanolysis of six 4-substituted 2-phenyl-5(4H)-oxazolones to (S)-methyl N-benzoyl-alpha-amino acid esters with 10-33% e.e and 72-81% yield.
关键词 CINCHONINE 5(4H)-oxazolone cataytic asymmetric reaction dynamic-kinetic resolution ENANTIOSELECTIVE
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An Efficient Asymmetric Domino Reaction of Amino Aldehyde to β,γ-Unsaturated a-Keto Esters Using trans-Perhydroindolic Acid as a Chiral Organocatalyst 被引量:2
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作者 申杰峰 安前进 +2 位作者 刘德龙 刘燕刚 张万斌 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2012年第11期2681-2687,共7页
An efficient asymmetric domino reaction of amino aldehyde to β,γ-unsaturated a-keto esters was achieved by using trans-perhydroindolic acid ld as a chiral organocatalyst with excellent asymmetric behavior. Under the... An efficient asymmetric domino reaction of amino aldehyde to β,γ-unsaturated a-keto esters was achieved by using trans-perhydroindolic acid ld as a chiral organocatalyst with excellent asymmetric behavior. Under the opti- mal reaction conditions, products with more than 99% de and up to 93% ee were obtained in high chemical yield (up to 98%) for a series of β,γ-unsaturated a-keto esters. The methodology provided an efficient route to dihydro- pyran derivatives containing many substituent groups (including amino groups). 展开更多
关键词 asymmetric domino reaction β γ-unsaturated a-keto esters trans-perhydroindolic acid ORGANOCATALYST
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Tetrahydrobenzo[5]helicenediol derivatives as additives for efficient proline-catalyzed asymmetric List-Lerner-Barbas aldol reactions of bulky aldehyde substrates 被引量:1
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作者 Lei Fang Weibin Lin Chuanfeng Chen 《Chinese Chemical Letters》 SCIE CAS CSCD 2018年第8期1223-1225,共3页
Tetrahydrobenzo[5]helicenediol(THB-[5]HDIOL) derivatives as additives for the efficient prolinecatalyzed asymmetric List-Lerner-Barbas(LLB) aldol reactions of bulky aldehyde substrates was described. It was found ... Tetrahydrobenzo[5]helicenediol(THB-[5]HDIOL) derivatives as additives for the efficient prolinecatalyzed asymmetric List-Lerner-Barbas(LLB) aldol reactions of bulky aldehyde substrates was described. It was found that with dibromo-substituted helical diols P-4 a/M-4 a as additives, the prolinecatalyzed LLB aldol reaction of 9-anthraldehyde and acetone gave the product in 83% yield and 99% ee.Transition state models revealed an edge-to-face p-p stacking between the anthracenyl group in TS(R)and the phenyl group of the additive, which might result in the high enantioselectivity. 展开更多
关键词 Helicenediol asymmetric aldol reaction Additive Bulky aldehyde substrate
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Highly Enantioselective Direct Asymmetric Aldol Reaction Catalyzed by 4,5-Methano-L-proline 被引量:1
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作者 Yukun Zhang Jun Zhu +1 位作者 Na Yu Han Yu 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2015年第2期171-174,共4页
The 4,5-methano-L-proline was used as chiral organocatalysts in direct asymmetric aldol reactions.Under the optimal conditions,excellent enantioselectivities(up to 99%ee)were obtained with high chemical yields(up to 9... The 4,5-methano-L-proline was used as chiral organocatalysts in direct asymmetric aldol reactions.Under the optimal conditions,excellent enantioselectivities(up to 99%ee)were obtained with high chemical yields(up to 95%)for a series of aldehydes using only 5 mol%catalyst loading.To show the practicality of the method,the reaction was tested at a large scale.The reaction was complete in 16 h,and the aldol product was obtained in 86%yield and 93%ee. 展开更多
关键词 asymmetric organocatalysis direct asymmetric aldol reaction 4 5-methano-L-proline
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Catalytic asymmetric Catellani-type reaction: A powerful tool for axial chirality construction 被引量:3
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作者 Yue Dong Renshuai Liu Wei Wang 《Green Synthesis and Catalysis》 2020年第2期83-85,共3页
This highlight summarizes a recent development of a catalytic enantioselective Catellani-type reaction for the synthesis of axially chiral biaryls.The chirality induction is solely governed by chiral norbornene ligand... This highlight summarizes a recent development of a catalytic enantioselective Catellani-type reaction for the synthesis of axially chiral biaryls.The chirality induction is solely governed by chiral norbornene ligand in the Pd mediated ortho C–H functionalization and ipso cross-coupling transformation.The preparative power of the methodology is demonstrated as a powerful manifold for the divergent synthesis of structurally diverse axially chiral biaryls and chiral fluorenols. 展开更多
关键词 Axially chiral biaryls asymmetric Catellani reaction C-H functionalization Cross coupling Divergent synthesis
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A rapid and sensitive method to detect mycobacterium tuberculosis DNA by fluorescence polarization 被引量:1
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作者 白玉杰 赵锦荣 +4 位作者 薛丽 刘爱翔 张文红 郭晏海 闫小君 《Journal of Medical Colleges of PLA(China)》 CAS 2004年第4期219-221,共3页
Objective: To develop a new high sensitivity, rapid and simple mycobacterium tuberculosis DNA detection method using fluorescence polarization technology. Methods: In our asymmetric PCR protocol, 100 times mole of TB-... Objective: To develop a new high sensitivity, rapid and simple mycobacterium tuberculosis DNA detection method using fluorescence polarization technology. Methods: In our asymmetric PCR protocol, 100 times mole of TB-R primer was added than in the usual symmetric PCR to get enough single strands PCR product. The probe TB-5′-TAMRA and PCR products were mixed in a tube and incubate for 5-15 min at 46 ℃.The polarization (mp) was measured using victor2 Multilabel Plate Reader. Results: Asymmetric and symmetric PCR products were analyzed by the FP method. Asymmetric PCR products are detected more sensitively than symmetric ones. The polarization values of probe associated with asymmetric products were much higher than with symmetric products. Conclusion: This fluorescence polarization assay in conjunction with asymmetric PCR is a powerful and widely applicable method for the rapid and sensitive detection of micro-organisms in clinical laboratories. 展开更多
关键词 mycobacterium tuberculosis asymmetric polymerase chain reaction fluorescence polarization
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Asymmetric Direct Aldol Reaction of Cyclohexanone Catalyzed by ( N'-BenzyI-N'-D-prolyl)-trans-4- hydroxy-L-proline Hydrazide
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作者 Cheng, Chuanling Wang, Wenliang 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2011年第1期196-198,共3页
A new proline catalyst, namely (N'-benzyl-N'-D-prolyl)-trans-4-hydroxy-L-proline hydrazide, has been prepared and proved to be a superior catalyst for the asymmetric aldol reaction of cyclohexanone and aromatic al... A new proline catalyst, namely (N'-benzyl-N'-D-prolyl)-trans-4-hydroxy-L-proline hydrazide, has been prepared and proved to be a superior catalyst for the asymmetric aldol reaction of cyclohexanone and aromatic aldehydes, affording up to 98 : 2 dr and 98% ee. 展开更多
关键词 asymmetric aldol reaction proline hydrazide ENANTIOSELECTIVITY DIASTEREOSELECTIVITY CYCLOHEXANONE
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