Org. and Biomol. Chem.

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Updated: 11 hours 41 min ago

A reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1,3-dimethylimidazolinium hexafluorophosphate

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4397-4406
DOI: 10.1039/C4OB00515E, PaperMitsuru Kitamura, So Kato, Masakazu Yano, Norifumi Tashiro, Yuichiro Shiratake, Mitsuyoshi Sando, Tatsuo Okauchi
Organic azides were synthesized from primary amines by diazo-transfer with a safe and stable crystalline reagent, 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP).
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Efficient one-step synthesis of 4-amino substituted phthalimides and evaluation of their potential as fluorescent probes

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4461-4470
DOI: 10.1039/C4OB00342J, PaperTomas Kindahl, Erik Chorell
Chemistry: One step, high yields, general, atom efficient, no additives. Compounds: Highly fluorescent and solvatochromic, many display non-toxic properties.
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A stereoselective approach to indolizidine and pyrrolizidine alkaloids: total synthesis of (-)-lentiginosine, (-)-epi-lentiginosine and (-)-dihydroxypyrrolizidine

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4454-4460
DOI: 10.1039/C4OB00461B, PaperShruti Vandana Kauloorkar, Vishwajeet Jha, Ganesh Jogdand, Pradeep Kumar
The total synthesis of (-)-lentiginosine, epi-1,2-lentiginosine and dihydroxypyrrolizidine is reported from an aldehyde as a starting material using organocatalysis and asymmetric dihydroxylation as key steps.
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Organocatalytic enantioselective construction of multi-functionalized spiro oxindole dienes

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4372-4385
DOI: 10.1039/C4OB00545G, PaperXiao-Fei Huang, Ya-Fei Zhang, Zheng-Hang Qi, Nai-Kai Li, Zhi-Cong Geng, Kun Li, Xing-Wang Wang
A highly stereoselective Michael-cyclization-tautomerization reaction of isatylidene malononitriles with [small alpha],[small alpha]-dicyanoalkenes was developed via organocatalysis. An anomalous temperature effect on the enantioselectivity is disclosed for this transformation.
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Using computational methods to explore improvements to Knolker's iron catalyst

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4361-4371
DOI: 10.1039/C4OB00353E, PaperXi Lu, Yawei Zhang, Nicholas Turner, Mingtao Zhang, Tonglei Li
Some improvements were predicted for Knolker's catalyst via density functional method.
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Rhodium(III)-catalyzed coupling of N-sulfonyl 2-aminobenzaldehydes with oxygenated allylic olefins through C-H activation

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4290-4294
DOI: 10.1039/C4OB00704B, CommunicationTingting Yang, Tao Zhang, Shangdong Yang, Shanshan Chen, Xingwei Li
N-Sulfonyl-2-aminobenzaldehyde undergoes C-H activation and coupling with oxygenated allylic olefins under redox-neutral conditions with high efficiency.
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Lewis acid promoted dual bond formation: facile synthesis of dihydrocoumarins and spiro-tetracyclic dihydrocoumarins

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4347-4360
DOI: 10.1039/C4OB00490F, PaperPedireddi Niharika, Bokka Venkat Ramulu, Gedu Satyanarayana
Lewis acid (FeCl3) mediated dual bond (C-C and C-O) formation for synthesis of 3,4-dihydrocoumarins is presented.
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Synthesis and biological evaluation of hybrids from farnesylthiosalicylic acid and hydroxylcinnamic acid with dual inhibitory activities of Ras-related signaling and phosphorylated NF-[small kappa]B

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4517-4530
DOI: 10.1039/C4OB00023D, PaperYong Ling, Zhiqiang Wang, Xuemin Wang, Ying Zhao, Wei Zhang, Xinyang Wang, Li Chen, Zhangjian Huang, Yihua Zhang
Hybrid 5f significantly inhibited both Ras-related signaling and phosphorylated NF-[small kappa]B, which may synergistically contribute to its apoptosis induction and tumor growth inhibition in vitro and in vivo.
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Scaffolded multiple cyclic peptide libraries for protein mimics by native chemical ligation

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4471-4478
DOI: 10.1039/C4OB00190G, PaperH. van de Langemheen, M. van Hoeke, H. C. Quarles van Ufford, J. A. W. Kruijtzer, R. M. J. Liskamp
The accessibility to collections, libraries and arrays of cyclic peptides is increasingly important since cyclic peptides may provide better mimics of the loop-like structures ubiquitously present in and - especially - on the surface of proteins.
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Hypervalent iodine: a powerful electrophile for asymmetric [small alpha]-functionalization of carbonyl compounds

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4278-4289
DOI: 10.1039/C4OB00318G, Review ArticleDao-Qing Dong, Shuang-Hong Hao, Zu-Li Wang, Chao Chen
Environmentally friendly hypervalent iodine reagents are unusually effective promoters of asymmetric [small alpha]-functionalization of carbonyl compounds.
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A highly efficient catalyst of a nitrogen-based ligand for the Suzuki coupling reaction at room temperature under air in neat water

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4511-4516
DOI: 10.1039/C3OB42517G, PaperShiwen Liu, Meiyun Lv, Daoan Xiao, Xiaogang Li, Xiuling Zhou, Mengping Guo
Glycine is used to prepare an air-stable and water-soluble catalyst for the Suzuki-Miyaura reaction. In the presence of 0.1% [PdCl2(NH2CH2COOH)2], excellent catalytic activity is observed at room temperature under air in neat water.
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"One-pot" access to dihydrofurans via tandem oxidative difunctionalization and ring contraction of aminopyrans

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4412-4420
DOI: 10.1039/C4OB00324A, PaperSanthosh Reddy Mandha, Manjula Alla, Jagadeesh Babu Nanubolu
A new strategy for the construction of dihydrofuran derivatives by one-pot tandem oxidative difunctionalization and base catalysed ring contraction of aminopyrans.
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A Friedel-Crafts alkylation mechanism using an aminoindanol-derived thiourea catalyst

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4503-4510
DOI: 10.1039/C4OB00348A, PaperDavid Roca-Lopez, Eugenia Marques-Lopez, Ana Alcaine, Pedro Merino, Raquel P. Herrera
Computational calculations based on experimental results shed light on the mechanistic proposal for a Friedel-Crafts alkylation reaction between indole and nitroalkenes, catalysed by a chiral aminoindanol-derived thiourea.
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Synthesis, physicochemical properties and antimicrobial activity of mono-/dinitroxyl amides

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4491-4502
DOI: 10.1039/C4OB00302K, PaperMiroslav Kavala, Vlasta Brezova, Lubomir Svorc, Zuzana Vihonska, Petra Olejnikova, Jan Moncol, Jozef Kozisek, Peter Herich, Peter Szolcsanyi
Novel TEMPO and PROXYL derivatives reveal (quasi)reversible redox behavior. The EWG-substituents increase their oxidation potential in comparison to the EDG-groups. Unlike pyrrolidinyl derivatives, the piperidinyl nitroxides inhibit the growth of Staphylococcus sp.
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Proline N-oxides: modulators of the 3D conformation of linear peptides through "NO-turns"

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4479-4490
DOI: 10.1039/C4OB00433G, PaperMajid D. Farahani, Bahareh Honarparvar, Fernando Albericio, Glenn E. M. Maguire, Thavendran Govender, Per I. Arvidsson, Hendrik G. Kruger
N-Oxide residues enforce turn conformations in peptides.
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Enhancing circularly polarised luminescence by extending the [small pi]-conjugation of axially chiral compounds

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4342-4346
DOI: 10.1039/C4OB00340C, PaperYoko Kitayama, Tomoyuki Amako, Nozomu Suzuki, Michiya Fujiki, Yoshitane Imai
[small pi]-Conjugated (R)- and (S)-2,2[prime or minute]-diphenyl-4-biphenanthrol (VAPOL) exhibited an efficient circularly polarised luminescence (CPL) ([similar]1.3 [times] 10-3) at 376 nm. By comparison, (R)- and (S)-3,3-diphenyl-2,2-bi-1-naphthol (VANOL) exhibited no CPL.
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Aggregation-induced emission enhancement upon Al3+ complexation with a tetrasulfonated calix[4]bisazacrown fluorescent molecular sensor

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4335-4341
DOI: 10.1039/C4OB00187G, PaperYi-Bin Ruan, Alexis Depauw, Isabelle Leray
A new water-soluble ligand bearing a tetrasulfonated calix[4]arene was constructed for ratiometric detection of Al3+ based on an aggregation-induced fluorescence enhancement mechanism.
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Synthesis and antimalarial activity of prodigiosenes

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4132-4142
DOI: 10.1039/C3OB42548G, PaperEstelle Marchal, Deborah A. Smithen, Md. Imam Uddin, Andrew W. Robertson, David L. Jakeman, Vanessa Mollard, Christopher D. Goodman, Kristopher S. MacDougall, Sherri A. McFarland, Geoffrey I. McFadden, Alison Thompson
Dibutyl tin complexes of prodigiosenes exhibit nanomolar IC50 values against 3D7 Plasmodium falciparum, with general toxicity demonstrably lower than that of the natural product.
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Versatile post-functionalization of the external shell of cowpea chlorotic mottle virus by using click chemistry

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4065-4069
DOI: 10.1039/C4OB00505H, CommunicationC. A. Hommersom, B. Matt, A. van der Ham, J. J. L. M. Cornelissen, N. Katsonis
We present the modification of the outer protein shell of cowpea chlorotic mottle virus (CCMV) with linear and strained alkyne groups for post-functionalization by click chemistry.
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Improving alkynyl(aryl)iodonium salts: 2-anisyl as a superior aryl group

2 June, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,4156-4162
DOI: 10.1039/C4OB00556B, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.David J. Hamnett, Wesley J. Moran
This article describes the effects of varying this iodoarene building block on the synthesis, reactivity and stability of these salts.
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