Royal Society of Chemistry

Synthesis of highly functionalized C60 fullerene derivatives and their applications in material and life sciences

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01663G, Review ArticleWeibo Yan, Stefan M. Seifermann, Philippe Pierrat, Stefan Brase
Highly functionalized fullerenes can be efficiently constructed by various techniques.
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Correction: Stereocontrolled lithiation/trapping of chiral 2-alkylideneaziridines: investigation into the role of the aziridine nitrogen stereodynamics

Org. and Biomol. Chem. - 22 October, 2014 - 09:54
Org. Biomol. Chem., 2014, 12,9028-9028
DOI: 10.1039/C4OB90144D, CorrectionRosmara Mansueto, Leonardo Degennaro, Jean-Francois Briere, Karen Griffin, Michael Shipman, Saverio Florio, Renzo Luisi
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Organocatalytic Michael addition-lactonisation of carboxylic acids using [small alpha],[small beta]-unsaturated trichloromethyl ketones as [small alpha],[small beta]-unsaturated ester equivalents

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,9016-9027
DOI: 10.1039/C4OB01788A, PaperLouis C. Morrill, Daniel G. Stark, James E. Taylor, Siobhan R. Smith, James A. Squires, Agathe C. A. D'Hollander, Carmen Simal, Peter Shapland, Timothy J. C. O'Riordan, Andrew D. Smith
Isothiourea HBTM-2.1 catalyses the Michael addition-lactonisation of 2-aryl and 2-alkenylacetic acids and [small alpha],[small beta]-unsaturated trichloromethyl ketones.
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Templated DNA ligation with thiol chemistry

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8823-8827
DOI: 10.1039/C4OB01552E, CommunicationDadong Li, Xiaojian Wang, Fubo Shi, Ruojie Sha, Nadrian C. Seeman, James W. Canary
Templated DNA ligation reactions are useful in a variety of contexts and have drawn much attention recently. Herein we describe two different DNA-templated ligation systems based on thiols and thiol-mediated chemistry. One system follows the principle of native chemical ligation reaction, and the other utilizes a thiol-disulfide exchange reaction.
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Efficient silver-catalyzed direct sulfenylation and selenylation of rich arenes

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01992J, PaperGuobing Yan, Arun Jyoti Borah, Lianggui Wang
An efficient protocol for silver/copper-cocatalyzed direct sulfenylation and selenylation of arenes with aryl disulfides and diselenides has been developed.
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Catalytic asymmetric Povarov reaction of isatin-derived 2-azadienes with 3-vinylindoles

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01741B, PaperHong-Hao Zhang, Xiao-Xue Sun, Jing Liang, Yue-Ming Wang, Chang-Chun Zhao, Feng Shi
The first catalytic asymmetric Povarov reaction of isatin-derived 2-azadienes with 3-vinylindoles has been established to construct a spiro[indolin-3,2[prime or minute]-quinoline] framework bearing an indole moiety.
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One pot synthesis of pyrrolo[3,4-c]quinolinone/pyrrolo[3,4-c]quinoline derivatives from 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC)

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01580K, PaperXin-Mou Lu, Jian Li, Zhong-Jian Cai, Rong Wang, Shun-Yi Wang, Shun-Jun Ji
An efficient and practical synthetic approach giving access to 2H-pyrrolo[3,4-c]quinolin-4(5H)-one/2H-pyrrolo[3,4-c]quinoline derivatives via a one pot van Leusen reaction and cyclization under basic conditions.
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A short designed semi-aromatic organic nanotube - synthesis, chiroptical characterization, and host properties

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8930-8941
DOI: 10.1039/C4OB01683A, PaperTorbjorn Wixe, Niels Johan Christensen, Sven Lidin, Peter Fristrup, Kenneth Warnmark
A short helical nanotube having its aromatic system perpendicular to its axis of propagation was synthesized and its properties were studied.
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Palladium-catalyzed coupling of N-tosylhydrazones and [small beta]-bromostyrene derivatives: new approach to 2H-chromenes

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01979B, CommunicationYamu Xia, Ying Xia, Yan Zhang, Jianbo Wang
A palladium-catalyzed cascade reaction that involves [small pi]-allylic palladium species generated from carbene migratory insertion leads to the formation of 2H-chromenes.
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Transition metal ion induced hydrogelation by amino-terpyridine ligands

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8836-8839
DOI: 10.1039/C4OB01867B, CommunicationSandip Bhowmik, Biswa Nath Ghosh, Kari Rissanen
Hydrogelation behavior of a new class of terpyridine based metallogelators are explored. The gelation and the gel morphology was found to be critically dependent on divalent metal ions, anions and on subtle structural changes on the gelator molecule.
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Addition of optically pure H-phosphinate to ketones: selectivity, stereochemistry and mechanism

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01574F, PaperYong-Ming Sun, Nana Xin, Zhong-Yuan Xu, Li-Juan Liu, Fan-Jie Meng, He Zhang, Bao-Ci Fu, Qiu-Ju Liang, Hong-Xing Zheng, Li-Jun Sun, Chang-Qiu Zhao, Li-Biao Han
A stability-controlled diastereoselective addition of a chiral P-H species to ketones afforded P,C-stereogenic [small alpha]-hydroxyphosphinates in excellent yields and dr.
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Catalytic asymmetric desymmetrization approaches to enantioenriched cyclopentanes

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01649A, PerspectiveMadhu Sudan Manna, Santanu Mukherjee
Asymmetric desymmetrization represents an excellent strategy for obtaining highly functionalized chiral building blocks. However, the application of this strategy for the synthesis of cyclopentane derivatives remained limited, when compared to cyclohexanes. Here, we give an overview of asymmetric desymmetrization reactions leading to enantioenriched cyclopentanes.
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Protein backbone engineering as a strategy to advance foldamers toward the frontier of protein-like tertiary structure

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8796-8802
DOI: 10.1039/C4OB01769B, PerspectiveZachary E. Reinert, W. Seth Horne
This Perspective surveys work on protein backbone engineering and its recent application to design heterogeneous backbones that adopt complex tertiary folds.
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Pseudo-cyclic structures of mono- and di-azaderivatives of malondialdehydes. Synthesis and conformational disentanglement by computational analyses

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8997-9010
DOI: 10.1039/C4OB01507J, PaperMaria P. Romero-Fernandez, Martin Avalos, Reyes Babiano, Pedro Cintas, Jose L. Jimenez, Mark E. Light, Juan C. Palacios
Aminoacroleins and vinamidines are structures featuring H-bonding and complex conformational and tautomeric equilibria, which have been dissected by computation.
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Synthesis of functionalized fulvenes: [3 + 2] annulation of ethyl [small alpha]-chlorocyclopropaneformates with 1,3-dicarbonyl compounds

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8828-8831
DOI: 10.1039/C4OB01973C, CommunicationYuequan Zhu, Min Zhang, Hongling Yuan, Yuefa Gong
An efficient method is reported to produce acidic multi-substituted fulvenes at high yields (up to 94%) through the base-promoted [3 + 2] annulation reaction of ethyl [small alpha]-chlorocyclopropaneformates with 1,3-dicarbonyl compounds.
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Metal-free, one-pot conversion of proline derivatives into 2-aryl-3-iodo pyrrolidines by a sequential scission-iodination-arylation process

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01372G, PaperVenkateswara Rao Batchu, Ivan Romero-Estudillo, Alicia Boto, Javier Miguelez
A sequential radical decarboxylation-oxidation-iodination-arylation process allows the metal-free, direct conversion of proline derivatives into 2-aryl-3-iodopyrrolidines, which are valuable precursors of a variety of heterocycles.
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Approaches to design non-covalent inhibitors for human granzyme B (hGrB)

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8952-8965
DOI: 10.1039/C4OB01874E, PaperMi-Sun Kim, Lauriane A. Buisson, Dean A. Heathcote, Haipeng Hu, D. Christopher Braddock, Anthony G. M. Barrett, Philip G. Ashton-Rickardt, James P. Snyder
A structure-based design campaign for non-covalent small molecule inhibitors of hGrB was carried out by virtual screening employing three constraints and probe site-mapping with FTMAP to identify ligand "hot spots".
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Chemical and biological evaluation of unusual sugars, [small alpha]-aculosides, as novel Michael acceptors

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8832-8835
DOI: 10.1039/C4OB01877J, CommunicationHiromasa Ikeda, Erika Kaneko, Shunsuke Okuzawa, Daisuke Takahashi, Kazunobu Toshima
Unusual sugars, [small alpha]-aculosides, were found to be novel and selective Michael acceptors to a thiol function of cysteine residues of proteins in living cells.
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A straightforward modification in the thrombin binding aptamer improving the stability, affinity to thrombin and nuclease resistance

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8840-8843
DOI: 10.1039/C4OB01475H, CommunicationVeronica Esposito, Maria Scuotto, Antonella Capuozzo, Rita Santamaria, Michela Varra, Luciano Mayol, Antonella Virgilio, Aldo Galeone
Introduction of inversion of polarity sites at the 5[prime or minute]- and/or 3[prime or minute]-end in the thrombin binding aptamer is a simple modification able to improve, at the same time, thermal stability, affinity to thrombin and nuclease resistance.
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The design, synthesis and biological evaluation of novel thiamin diphosphate analog inhibitors against the pyruvate dehydrogenase multienzyme complex E1 from Escherichia coli

Org. and Biomol. Chem. - 22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8911-8918
DOI: 10.1039/C4OB01347F, PaperLingling Feng, Junbo He, Haifeng He, Lulu Zhao, Lingfu Deng, Li Zhang, Lin Zhang, Yanliang Ren, Jian Wan, Hongwu He
Optimal binding mode for the novel potent inhibitor 4j against PDHc-E1 from E. coli.
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