Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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A theoretical study on the catalytic mechanism of the retaining [small alpha]-1,2-mannosyltransferase Kre2p/Mnt1p: the impact of different metal ions on catalysis

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4201-4210
DOI: 10.1039/C4OB00286E, PaperAdela Bobovska, Igor Tvaroska, Juraj Kona
The catalysis of the glycosyltransferase Kre2p/Mnt1p in the presence of various metal ions (Mn2+, Mg2+, Zn2+ and Ca2+) is predicted as a stepwise SNi-like reaction.
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Microwave-assisted synthesis of potent PDE7 inhibitors containing a thienopyrimidin-4-amine scaffold

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4233-4242
DOI: 10.1039/C4OB00175C, PaperAna I. Sanchez, Ricardo Meneses, Jose M. Minguez, Araceli Nunez, Rafael R. Castillo, Fabiana Filace, Carolina Burgos, Juan J. Vaquero, Julio Alvarez-Builla, Alvaro Cortes-Cabrera, Federico Gago, Emma Terricabras, Victor Segarra
Thienopyrimidin-4-amines have been synthesized, evaluated and modelled as phosphodiesterase inhibitors.
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Preparation of functionalized heteroaromatics using an intramolecular Wittig reaction

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4044-4050
DOI: 10.1039/C4OB00464G, PerspectiveUtpal Das, Yi-Ling Tsai, Wenwei Lin
An approach for the synthesis of heteroaromatics starting from electron-deficient olefins (or aldehydes and acylimines), acyl chlorides and phosphines using an intramolecular Wittig reaction as the key step is described.
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The asymmetric Cu(II)-indolinylmethanol complex catalyzed Diels-Alder reaction of 2-vinylindoles with [small beta],[gamma]-unsaturated [small alpha]-ketoesters: an efficient route to functionalized tetrahydrocarbazoles

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4172-4176
DOI: 10.1039/C4OB00196F, PaperBanlai Ouyang, Tingting Yu, Renshi Luo, Gui Lu
An efficient asymmetric Diels-Alder reaction of 2-vinylindoles with [small beta],[gamma]-unsaturated [small alpha]-ketoesters for the synthesis of functionalized tetrahydrocarbazoles.
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sp3 C-H oxidation by remote H-radical shift with oxygen- and nitrogen-radicals: a recent update

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4051-4060
DOI: 10.1039/C4OB00469H, Review ArticleShunsuke Chiba, Hui Chen
This review updates on recent advances in aliphatic sp3 C-H bond oxidation by remote H-radical abstraction with oxygen- and nitrogen-radicals classifying by the type of the radical precursors.
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Total synthesis of an anticancer norsesquiterpene alkaloid isolated from the fungus Flammulina velutipes

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4098-4103
DOI: 10.1039/C4OB00300D, PaperK. Kashinath, Prakash D. Jadhav, D. Srinivasa Reddy
Total synthesis of a norsesquiterpene alkaloid has been achieved in racemic and enantiopure forms for the first time.
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Cascade nitrosation and addition-elimination of nitroacetanilides for the highly efficient synthesis of 1,4,2,5-dioxadiazine derivatives

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4192-4200
DOI: 10.1039/C3OB42487A, PaperShanyan Mo, Peipei Huang, Jiaxi Xu
An efficient synthesis of 1,4,2,5-dioxadiazine-3,6-dicarboxamides via cascade nitrosation and addition-elimination of nitroacetanilides.
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Rhodium(III)-catalyzed formal oxidative [4 + 1] cycloaddition of benzohydroxamic acids and [small alpha]-diazoesters. A facile synthesis of functionalized benzolactams

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4112-4116
DOI: 10.1039/C4OB00512K, PaperHon-Wah Lam, Ka-Yi Man, Wai-Wing Chan, Zhongyuan Zhou, Wing-Yiu Yu
A mild and regioselective Rh(III)-catalyzed oxidative [4 + 1] cycloaddition of benzohydroxamic acids and [small alpha]-diazoesters for the synthesis of benzolactam is described.
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Non-stoichiometric O-acetylation of Shigella flexneri 2a O-specific polysaccharide: synthesis and antigenicity

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4218-4232
DOI: 10.1039/C3OB42586J, PaperCharles Gauthier, Pierre Chassagne, Francois-Xavier Theillet, Catherine Guerreiro, Francoise Thouron, Farida Nato, Muriel Delepierre, Philippe J. Sansonetti, Armelle Phalipon, Laurence A. Mulard
Synthetic functional mimics of the O-antigen from Shigella flexneri 2a are seen as promising vaccine components against endemic shigellosis.
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Copper-catalyzed bis-arylations of alkenes leading to oxindole derivatives

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4070-4073
DOI: 10.1039/C4OB00576G, CommunicationLiangliang Shi, Yuyuan Wang, Haijun Yang, Hua Fu
A simple and practical copper-catalyzed approach to oxindole derivatives by copper-catalyzed bis-arylation of N-alkyl-N-phenylacrylamides with diaryliodonium triflates has been developed under mild conditions, and the method is of tolerance towards some functional groups in the substrates.
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Zinc mediated allylations of chlorosilanes promoted by ultrasound: Synthesis of novel constrained sila amino acids

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4093-4097
DOI: 10.1039/C4OB00294F, CommunicationRemya Ramesh, D. Srinivasa Reddy
A simple, fast and efficient method for allylation and propargylation of chlorosilanes through zinc mediation and ultrasound promotion is reported. As a direct application of the resulting bis-allylsilanes, three novel, constrained sila amino acids are prepared for the first time.
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Quantum mechanistic insights on aryl propargyl ether Claisen rearrangement

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4163-4171
DOI: 10.1039/C4OB00388H, PaperVenkatesan Srinivasadesikan, Jiun-Kuang Dai, Shyi-Long Lee
The mechanism of aryl propargyl ether Claisen rearrangement in gas and solvent phase was investigated using DFT methods.
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Organocatalytic asymmetric decarboxylative cyanomethylation of isatins using L-proline derived bifunctional thiourea

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4186-4191
DOI: 10.1039/C4OB00271G, PaperV. Pratap Reddy Gajulapalli, Poopathy Vinayagam, Venkitasamy Kesavan
Asymmetric decarboxylative cyanomethylation of isatins using L-proline derived bifunctional thiourea to access cyanomethylated 3-hydroxyoxindoles in good yields and enantioselectivities.
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The diene-transmissive hetero-Diels-Alder reaction of 2-vinyl [small alpha],[small beta]-unsaturated aldimines: stereoselective synthesis of hexahydroquinazolin-2-ones

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4061-4064
DOI: 10.1039/C4OB00224E, CommunicationSatoru Kobayashi, Kenji Kudo, Ai Ito, Satoru Hirama, Takashi Otani, Takao Saito
The tandem Diels-Alder methodology of cross-conjugated 1-azatrienes for synthesis of crossed bis-cycloadducts with high chemo-, regio- and stereoselectivities is described.
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Improved hemicryptophane hosts for the stereoselective recognition of glucopyranosides

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4211-4217
DOI: 10.1039/C4OB00156G, PaperAline Schmitt, Olivier Perraud, Elina Payet, Bastien Chatelet, Benjamin Bousquet, Marion Valls, Daniele Padula, Lorenzo Di Bari, Jean-Pierre Dutasta, Alexandre Martinez
Slight changes in the chiral environment of enantiopure hemicryptophanes improve the stereoselective recognition of [small alpha] and [small beta] anomers of glucopyranosides.
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Gold-catalyzed tandem Diels-Alder reactions of enynals/enynones with alkenes: generation and trapping of cyclic o-QDMs

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4104-4111
DOI: 10.1039/C4OB00321G, PaperShifa Zhu, Lang Hu, Huanfeng Jiang
Gold-catalyzed generation of the highly reactive cyclic o-QDM species and application in preparation of structurally unique propeller-like molecules.
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A rapid entry to amino acid derived diverse 3,4-dihydropyrazines and dihydro[1,2,3]triazolo[1,5-a]pyrazines through 1,3-dipolar cycloaddition

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3976-3985
DOI: 10.1039/C4OB00639A, PaperSaurav Bera, Gautam Panda
Practical synthesis of diverse 3,4-dihydropyrazines, 6,7-dihydro-[1,2,3]triazolopyrazines and 7,8-dihydro-[1,2,3]triazolodiazepines through intramolecular 1,3-dipolar cycloaddition from amino acid derived intermediates is described.
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Fast imine equilibration and its consequences for the evaluation of dynamic combinatorial libraries

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3827-3830
DOI: 10.1039/C4OB00507D, CommunicationK. Ziach, A. Kulesza, J. Jurczak
An example of the interplay between the templation and a very fast reequilibration of a DCL of imines that occurs upon a solvent change is reported. Such seemingly "irrelevant" details of the procedure like imine dissolution time may dictate the outcome of the whole reaction.
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Protecting group free synthesis of urea-linked glycoconjugates: efficient synthesis of [small beta]-urea glycosides in aqueous solution

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3924-3931
DOI: 10.1039/C3OB42452A, PaperYoshiyasu Ichikawa, Takahiro Minami, Shohei Kusaba, Nobuyoshi Saeki, Yuta Tonegawa, Yumiko Tomita, Keiji Nakano, Hiyoshizo Kotsuki, Toshiya Masuda
The one step process, involving reactions between urea and protecting group free D-glucose, N-acetyl-D-glucosamine or D-xylose in acidic aqueous solution, furnishes the corresponding [small beta]-urea glycosides.
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PEGylated meso-arylporpholactone metal complexes as optical cyanide sensors in water

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3991-4001
DOI: 10.1039/C4OB00697F, PaperJill L. Worlinsky, Steven Halepas, Christian Bruckner
A number of water-soluble metal complexes of PEGylated meso-fluorophenylporpholactones display a specific optical response upon addition of cyanide.
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