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C 3-Symmetric chiral trisimidazoline-catalyzed Friedel-Crafts (FC)-type reaction

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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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Efficient asymmetric synthesis of N-protected-[small beta]-aryloxyamino acids via regioselective ring opening of serine sulfamidate carboxylic acid

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01047G, PaperRajesh Malhotra, Tushar K. Dey, Swarup Dutta, Sourav Basu, Saumen Hajra
First regioselective ring opening of serine derived cyclic sulfamidate with ArONa is developed to provide an easy and direct access of a variety of N-Boc- and N-PMB protected [small beta]-aryloxy-[small alpha]-amino acids with complete retention of enantiopurity in moderate to high yields.
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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

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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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Highly enantioselective synthesis of bisoxindoles with two vicinal quaternary stereocenters via Lewis base mediated addition of oxindoles to isatin-derived ketimines

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,6085-6088
DOI: 10.1039/C4OB01039F, CommunicationZhongkai Tang, Yan Shi, Haibin Mao, Xuebin Zhu, Weipeng Li, Yixiang Cheng, Wen-Hua Zheng, Chengjian Zhu
A highly efficient method provides access to the bisoxindole structure moiety with two vicinal quaternary stereogenic centers (>99 : 1 dr, >99% ee).
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Copper catalyzed C-O bond formation via oxidative cross-coupling reaction of aldehydes and ethers

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00862F, CommunicationQuan Wang, Hao Zheng, Wen Chai, Dianyu Chen, Xiaojun Zeng, Renzhong Fu, Rongxin Yuan
A practical and efficient construction of C-O bonds via oxidative cross-coupling reaction of aldehydes and ethers has been realized under open air. When 2 mol% copper was used as the catalyst, various [small alpha]-acyloxy ethers were obtained with up to 93% isolated yield.
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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

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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.
The content of this RSS Feed (c) The Royal Society of Chemistry

Rapid discovery of potent [small alpha]-fucosidase inhibitors by in situ screening of a library of (pyrrolidin-2-yl)triazoles

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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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Catalytic asymmetric nucleophilic openings of 3-substituted oxetanes

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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.
The content of this RSS Feed (c) The Royal Society of Chemistry

From in vitro to in cellulo: structure-activity relationship of (2-nitrophenyl)methanol derivatives as inhibitors of PqsD in Pseudomonas aeruginosa

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

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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