Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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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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Degradation of [small alpha]-melanocyte-stimulating hormone photosensitized by pterin

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3877-3886
DOI: 10.1039/C4OB00434E, PaperCarolina Castano, Carolina Lorente, Nathalie Martins-Froment, Esther Oliveros, Andres H. Thomas
The reaction is initiated by an electron transfer and produces chemical changes in at least tryptophan and tyrosine residues.
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Convergent and enantioselective syntheses of cytosolic phospholipase A2[small alpha] inhibiting N-(1-indazol-1-ylpropan-2-yl)carbamates

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,4021-4030
DOI: 10.1039/C4OB00535J, PaperTom Sundermann, Martina Arnsmann, Julian Schwarzkopf, Walburga Hanekamp, Matthias Lehr
A convergent synthesis for 4 and enantioselective syntheses for (R)-4 and (S)-4 starting from a (R)-serine derived oxazolidine were developed.
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19F NMR spectroscopy monitors ligand binding to recombinantly fluorine-labelled b[prime or minute]x from human protein disulphide isomerase (hPDI)

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3808-3812
DOI: 10.1039/C4OB00699B, CommunicationOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Rose Curtis-Marof, Denisa Doko, Michelle L. Rowe, Kirsty L. Richards, Richard A. Williamson, Mark J. Howard
Fluoroindole recombinant protein labelling enables a 19F NMR study to observe protein-ligand binding and dissociation constant determination.
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Synthesis and properties of chemiluminescent acridinium ester labels with fluorous tags

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3887-3901
DOI: 10.1039/C4OB00456F, PaperAnand Natrajan, David Wen, David Sharpe
Acridinium dimethylphenyl esters are highly sensitive chemiluminescent labels that are used in clinical diagnostics.
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Synthesis of new asymmetric xanthene dyes via catalyst-free SNAr with sulfur nucleophiles

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3816-3820
DOI: 10.1039/C4OB00533C, CommunicationMichaela Kotaskova, Okan Osman Oglou, Mark Helm
An unusual SNAr with sulfur nucleophiles on electron rich aromatic xanthenes affords a new class of photostable asymmetric thioether xanthene dyes.
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Development of a traceable linker containing a thiol-responsive amino acid for the enrichment and selective labelling of target proteins

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3821-3826
DOI: 10.1039/C4OB00622D, CommunicationJun Yamamoto, Masaya Denda, Nami Maeda, Miku Kita, Chiaki Komiya, Tomohiro Tanaka, Wataru Nomura, Hirokazu Tamamura, Youichi Sato, Aiko Yamauchi, Akira Shigenaga, Akira Otaka
A traceable linker that is potentially applicable to identification of a target protein of interest was developed.
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First total syntheses of chrestifoline-B and (+/-)-chrestifoline-C, and improved synthetic routes to bismurrayafoline-A, bismurrayafolinol and chrestifoline-D

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3831-3835
DOI: 10.1039/C4OB00609G, CommunicationCarsten Borger, Arndt W. Schmidt, Hans-Joachim Knolker
We describe an efficient synthesis of the methylene-bridged biscarbazole alkaloids bismurrayafoline-A, bismurrayafolinol and chrestifoline B-D using an Ullmann-type coupling at the benzylic position.
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Synthesis of [small alpha],[small beta]-unsaturated amides and iminocoumarins from N,N-disulfonyl ynamides with aldehydes via the ketenimine intermediate

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3986-3990
DOI: 10.1039/C4OB00513A, PaperLian Yu, Jian Cao
A novel synthesis of [small alpha],[small beta]-unsaturated amides from N,N-disulfonyl ynamides with aldehydes was developed. By utilization of salicylaldehydes, a variety of substituted iminocoumarins were prepared.
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Metal-free aerobic oxidative C-N bond cleavage of tertiary amines for the synthesis of N-heterocycles with high atom efficiency

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3802-3807
DOI: 10.1039/C4OB00578C, CommunicationXiuling Chen, Tieqiao Chen, Yongbo Zhou, Daoqing Han, Li-Biao Han, Shuang-Feng Yin
An efficient metal-free aerobic C-N bond cleavage of tertiary amines has been developed to construct N-heterocycles using molecular oxygen as the sole oxidant with high atom efficiency. All of the three alkyl groups in tertiary amines can be utilized and transformed into N-heterocycles.
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