Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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C 3-Symmetric chiral trisimidazoline-catalyzed Friedel-Crafts (FC)-type reaction

29 July, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,5827-5830
DOI: 10.1039/C4OB00925H, CommunicationShinobu Takizawa, Shuichi Hirata, Kenichi Murai, Hiromichi Fujioka, Hiroaki Sasai
The first imidazoline-catalyzed enantioselective Friedel-Crafts (FC)-type reaction was established using C3-symmetric chiral trisimidazolines.
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Catalytic asymmetric nucleophilic openings of 3-substituted oxetanes

29 July, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,6028-6032
DOI: 10.1039/C4OB00920G, PerspectiveZhaobin Wang, Zhilong Chen, Jianwei Sun
Important progress has been made in catalytic asymmetric ring-opening of 3-substituted oxetanes, but significant challenges and opportunities remain.
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One-pot pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes for synthesis of highly functionalized hexa-substituted 1,4-dihydropyridines

29 July, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,6223-6238
DOI: 10.1039/C4OB00628C, PaperH. Surya Prakash Rao, A. Parthiban
Pseudo three-component condensation of aliphatic/aromatic/[small alpha],[small beta]-unsaturated aldehydes and nitroketene-N,S-acetals to afford diversely functionalized hexa-substituted 1,4-dihydropyridines under 2-aminopyridine catalysis was achieved.
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CuI-catalyzed cross-coupling of terminal alkynes with dialkoxycarbenes: a general method for the synthesis of unsymmetrical propargylic acetals

29 July, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,6215-6222
DOI: 10.1039/C4OB00614C, PaperTiebo Xiao, Ping Zhang, Yang Xie, Jun Wang, Lei Zhou
A general source of dialkoxycarbenes, 2,2-dialkoxy-5,5-dimethyl-[capital Delta]3-1,3,4-oxadiazolines, have been successfully employed as coupling partners in CuI-catalyzed cross-coupling reactions with terminal alkynes, which afforded various unsymmetrical propargylic acetals in good yields.
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Organic synthetic transformations using organic dyes as photoredox catalysts

29 July, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,6059-6071
DOI: 10.1039/C4OB00843J, Review ArticleOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Shunichi Fukuzumi, Kei Ohkubo
This review article presents various photocatalytic transformation such as oxygenation, halogenation and C-C bond formation with organic photoredox catalysts.
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From in vitro to in cellulo: structure-activity relationship of (2-nitrophenyl)methanol derivatives as inhibitors of PqsD in Pseudomonas aeruginosa

29 July, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,6094-6104
DOI: 10.1039/C4OB00707G, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Michael P. Storz, Giuseppe Allegretta, Benjamin Kirsch, Martin Empting, Rolf W. Hartmann
More than 60 derivatives of (2-nitrophenyl)methanol were synthesized and evaluated regarding their potency to inhibit PqsD. In vitro and in cellulo structure-activity relationships were derived.
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Catalytic functionalization of tertiary alcohols to fully substituted carbon centres

29 July, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,6033-6048
DOI: 10.1039/C4OB00718B, Review ArticleLong Chen, Xiao-Ping Yin, Cui-Hong Wang, Jian Zhou
This review summarizes the recent progresses in the catalytic nucleophilic substitution of tertiary alcohols using carbon or heteroatom based nucleophiles for the efficient, diverse and atom economical construction of fully substituted carbon centres, and discusses synthetic opportunities that are still open.
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Recent advances in the synthesis of nitroolefin compounds

29 July, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,6049-6058
DOI: 10.1039/C4OB00573B, Review ArticleGuobing Yan, Arun Jyoti Borah, Lianggui Wang
This review focuses on recent achievements in nitroolefin synthesis and the mechanisms of the reactions are also discussed.
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Palladium mediated intramolecular multiple C-X/C-H cross coupling and C-H activation: synthesis of carbazole alkaloids calothrixin B and murrayaquinone A

29 July, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,6105-6113
DOI: 10.1039/C4OB00493K, PaperSrinivasan A. Kaliyaperumal, Shyamapada Banerjee, Syam Kumar U. K.
Straightforward palladium mediated syntheses of calothrixin B and murrayaquinone A are described.
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Mercaptobenzoic acid-palladium(0) complexes as active catalysts for S-benzylation with benzylic alcohols via ([small eta]3-benzyl)palladium(II) cations in water

27 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5964-5972
DOI: 10.1039/C4OB00688G, PaperHidemasa Hikawa, Isao Azumaya
Mercaptobenzoic acid-palladium(0) complexes show high catalytic activity for S-benzylation with benzylic alcohols via the ([small eta]3-benzyl)palladium(II) cation in water. The catalytic system can be performed using only 2.5 mol% Pd2(dba)3 without the phosphine ligand or other additives.
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Palladium-catalyzed synthesis of isoindoloquinazolinones via dicarbonylation of 1,2-dibromoarenes

27 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5835-5838
DOI: 10.1039/C4OB01103A, CommunicationJianbin Chen, Helfried Neumann, Matthias Beller, Xiao-Feng Wu
The first example of palladium-catalyzed carbonylative synthesis of isoindoloquinazolinones has been developed. Using 1,2-dibromobenzenes and 2-aminobenzyl amine as substrates, the products were isolated in moderate to good yields with the installation of two molecules of CO.
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Pyridine-phosphinimine ligand-accelerated Cu(I)-catalyzed azide-alkyne cycloaddition for preparation of 1-(pyridin-2-yl)-1,2,3-triazole derivatives

27 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5954-5963
DOI: 10.1039/C4OB01176G, PaperRanfeng Sun, Huangdong Wang, Jianfeng Hu, Jiudong Zhao, Hao Zhang
A new phosphinimine ligand was used in the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction of tetrazolo[1,5-a]pyridines (not active in traditional CuAAC reactions) and alkynes for the first time and a series of 1-(pyridin-2-yl)-1,2,3-triazole derivatives were prepared.
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Monitoring and inhibition of Plk1: amphiphilic porphyrin conjugated Plk1 specific peptides for its imaging and anti-tumor function

27 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5876-5882
DOI: 10.1039/C4OB00853G, PaperHongguang Li, Chi-Fai Chan, Wai-Lun Chan, Sam Lear, Steven L. Cobb, Nai-Ki Mak, Terrence Chi-Kong Lau, Rongfeng Lan, Wai-Kwok Wong, Ka-Leung Wong
Polo-like kinase 1 (Plk1) is well-known for taking part in cell cycle progression and regulation.
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One-pot synthesis of polysubstituted 3-acylpyrroles by cooperative catalysis

27 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5822-5826
DOI: 10.1039/C4OB01019A, CommunicationHai-Lei Cui, Fujie Tanaka
Polysubstituted 3-acylpyrroles were synthesized from readily available unsaturated ketones and N-substituted propargylated amines via an aza-Michael/alkyne carbocyclization cascade followed by oxidation in one pot.
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An unnatural amino acid based fluorescent probe for phenylalanine ammonia lyase

27 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5818-5821
DOI: 10.1039/C4OB00914B, CommunicationZhenlin Tian, Weiping Zhu, Yufang Xu, Xuhong Qian
An unnatural amino acid based fluorescent probe 2a-LP was designed and synthesized. 2a-LP exhibited an excellent response to phenylalanine ammonia lyase both in Tris-HCl buffer and tomato samples, and was used as an intracellular sensor for phenylalanine ammonia lyase imaging.
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New multi-target-directed small molecules against Alzheimer's disease: a combination of resveratrol and clioquinol

27 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5936-5944
DOI: 10.1039/C4OB00998C, PaperFei Mao, Jun Yan, Jianheng Li, Xian Jia, Hui Miao, Yang Sun, Ling Huang, Xingshu Li
Compound 10c exhibited excellent MTDL properties: excellent abilities to moderate A[small beta] aggregation, potential antioxidant behaviour and biometal chelation.
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Rapid discovery of potent [small alpha]-fucosidase inhibitors by in situ screening of a library of (pyrrolidin-2-yl)triazoles

27 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5898-5904
DOI: 10.1039/C4OB00931B, PaperPilar Elias-Rodriguez, Elena Moreno-Clavijo, Ana T. Carmona, Antonio J. Moreno-Vargas, Inmaculada Robina
The fucosidase inhibitory activity of a library of (pyrrolidin-2-yl)triazoles generated by CuAAC can be in situ analyzed, avoiding tedious purification steps. A potent and selective inhibitor was identified.
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Palladium-catalyzed ortho-functionalization of azoarenes with aryl acylperoxides

25 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5866-5875
DOI: 10.1039/C4OB00993B, PaperCheng Qian, Dongen Lin, Yuanfu Deng, Xiao-Qi Zhang, Huanfeng Jiang, Guang Miao, Xihao Tang, Wei Zeng
With the aid of an azo directing group, a Pd-catalyzed ortho-sp2 C-H bond activation/functionalization of azoarenes with aryl acyl peroxides has been explored. This transformation provides convenient access to regioselectively introducing acyloxyl and aryl group onto azoarenes.
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Synthesis and evaluation of the anticancer activity of albiziabioside A and its analogues as apoptosis inducers against human melanoma cells

25 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5928-5935
DOI: 10.1039/C4OB00874J, PaperGaofei Wei, Shuai Wang, Shanshan Cui, Jia Guo, Yongxiang Liu, Yang Liu, Maosheng Cheng
We have efficiently synthesized albiziabioside A (1) together with its six disaccharide analogues and evaluated their cytotoxicity against six different skin cancer cells. The results provide for the first time a basic mechanism for the anticancer activity of 1.
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Electrochemical behaviour of new dimeric esters and amides derived from caffeic acid in dimethylsulfoxide

25 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5981-5989
DOI: 10.1039/C4OB00823E, PaperAnalilia Sanchez, Omar Martinez-Mora, Evelin Martinez-Benavidez, Javier Hernandez, Zaira Dominguez, Magali Salas-Reyes
Small differences in the connectors of four new dimeric derivatives of caffeic acid exert interesting changes on their electrochemical behaviour.
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