Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Molecular recognition of upper rim functionalized cavitand and its unique dimeric capsule in the solid state

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1647-1653
DOI: 10.1039/C4OB02251C, PaperMutsumi Kobayashi, Mei Takatsuka, Ryo Sekiya, Takeharu Haino
Calix[4]resorcinarene-based cavitand recognized the methyl group of the guests to form 1 : 1 host-guest complexes. In the solid state, the cavitand formed a dimeric capsule in which two molecules of nitromethane were entrapped by weak noncovalent interactions.
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Computational study on the intramolecular self-organization of the macrorings of some 'giant' cyclodextrins (CDn, n = 40, 70, 85, 100)

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1680-1689
DOI: 10.1039/C4OB02218A, PaperPetko M. Ivanov, Emanouil J. Atanassov, Carlos Jaime
A limited number of modes determine the overall deformations of the macrorings, which may have more than one cavity. Accordingly, they have the potential to accommodate more than one substrate molecule.
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Divergolide congeners illuminate alternative reaction channels for ansamycin diversification

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1618-1623
DOI: 10.1039/C4OB02244K, CommunicationLing Ding, Jakob Franke, Christian Hertweck
Isolation and structure elucidation of six new divergolides reveal unusual ansamycin diversification reactions including formation of the unusual isobutenyl side chain from a branched polyketide synthase extender unit, azepinone ring closure, macrolide ring contraction and formation of a seco variant by a neighboring group-assisted decarboxylation.
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Reactivity of aldehydes at the air-water interface. Insights from molecular dynamics simulations and ab initio calculations

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1673-1679
DOI: 10.1039/C4OB02029D, PaperMarilia T. C. Martins-Costa, Francisco F. Garcia-Prieto, Manuel F. Ruiz-Lopez
Computer simulations show that solvation effects at the air-water interface significantly influence the chemistry of aldehydes, enhancing for instance the benzaldehyde photolysis rate constant by one order of magnitude.
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UV-visible and 1H-15N NMR spectroscopic studies of colorimetric thiosemicarbazide anion sensors

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1662-1672
DOI: 10.1039/C4OB02091J, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Kristina N. Farrugia, Damjan Makuc, Agnieszka Podborska, Konrad Szacilowski, Janez Plavec, David C. Magri
Four model thiosemicarbazide anion chemosensors containing three N-H bonds, substituted with phenyl and/or 4-nitrophenyl units, were synthesised and studied for their anion binding abilities with hydroxide, fluoride, acetate, dihydrogen phosphate and chloride.
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Anion binding and transport properties of cyclic 2,6-bis(1,2,3-triazol-1-yl)pyridines

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1654-1661
DOI: 10.1039/C4OB02236J, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Tamara Merckx, Cally J. E. Haynes, Louise E. Karagiannidis, Harriet J. Clarke, Katie Holder, Alexandra Kelly, Graham J. Tizzard, Simon J. Coles, Peter Verwilst, Philip A. Gale, Wim Dehaen
The anion binding and membrane transport properties of a series of cyclic 2,6-bis-(1,2,3-triazolyl)-pyridine receptors with thiourea functionalities are reported.
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Studies towards asymmetric synthesis of 4(S)-11-dihydroxydocosahexaenoic acid (diHDHA) featuring cross-coupling of chiral stannane under mild conditions

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1624-1628
DOI: 10.1039/C4OB02324B, CommunicationRui Wang, John R. Falck
An efficient and asymmetric synthesis approach towards the biologically interesting molecule 4(S)-11-dihydroxydocosahexaenoic acid (diHDHA) was developed. This protocol mainly relied on our mild cross-coupling and asymmetric stannylation.
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Chiral nanostructuring of multivalent macrocycles in solution and on surfaces

2 February, 2015 - 09:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02643H, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Marco Caricato, Arnaud Delforge, Davide Bonifazi, Daniele Dondi, Andrea Mazzanti, Dario Pasini
A chiral, multivalent macrocycle assembles upon metal-pyridine coordination into ordered nanostructures in solution and on surfaces.
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Asymmetric metal free [small beta]-boration of [small alpha],[small beta]-unsaturated imines assisted by (S)-MeBoPhoz

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1328-1332
DOI: 10.1039/C4OB02478H, CommunicationEnrico La Cascia, Xavier Sanz, Carles Bo, Andrew Whiting, Elena Fernandez
The adduct [MeO [rightward arrow] Bpin-Bpin]- efficiently mediates the [small beta]-boration of [small alpha],[small beta]-unsaturated imines formed in situ.
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Acid-promoted transformations of 1-(diphenylphosphoryl)allenes: synthesis of novel 1,4-dihydrophosphinoline 1-oxides

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1333-1338
DOI: 10.1039/C4OB02269F, CommunicationAlexander S. Bogachenkov, Albina V. Dogadina, Vadim P. Boyarskiy, Aleksander V. Vasilyev
1-(Diphenylphosphoryl)alka-1,2-dienes in acids (TfOH, FSO3H, H2SO4) give (3-hydroxyalk-1-en-1-yl)diphenylphosphine oxides, that are further converted into 1-phenyl-1,4-dihydrophosphinoline 1-oxides. The latter compounds are directly formed from these 1,2-dienes under the action of AlCl3.
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Copper-catalyzed O-arylation of N-protected 1,2-aminoalcohols using functionalized trivalent organobismuth reagents

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1322-1327
DOI: 10.1039/C4OB02497D, CommunicationPauline Petiot, Julien Dansereau, Martin Hebert, Imene Khene, Tabinda Ahmad, Samira Samaali, Maxime Leroy, Francis Pinsonneault, Claude Y. Legault, Alexandre Gagnon
The O-arylation of 1,2-aminoalcohols using functionalized triarylbismuth reagents is reported.
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"AND" luminescent "reactive" molecular logic gates: a gateway to multi-analyte bioimaging and biosensing

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1294-1306
DOI: 10.1039/C4OB02076F, Review ArticleAnthony Romieu
This feature article focuses on the recent development of "AND" luminescent molecular logic gates, in which the optical output is produced in response to multiple (bio)chemical inputs and through cascades of covalent bond-modifying reactions triggered by target (bio)analytes, for biosensing and bioimaging applications in complex media.
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Consecutive three-component synthesis of (hetero)arylated propargyl amides by chemoenzymatic aminolysis-Sonogashira coupling sequence

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1571-1576
DOI: 10.1039/C4OB02386B, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.Sidra Hassan, Anja Ullrich, Thomas J. J. Muller
(Hetero)arylated propargyl amides are efficiently prepared by consecutive chemoenzymatic three-component synthesis based upon lipase catalyzed aminolysis followed by Sonogashira coupling.
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E- or Z-Selective synthesis of 4-fluorovinyl-1,2,3-triazoles with fluorinated second-generation Julia-Kocienski reagents

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1536-1549
DOI: 10.1039/C4OB02179G, PaperRakesh Kumar, Govindra Singh, Louis J. Todaro, Lijia Yang, Barbara Zajc
Second-generation Julia-Kocienski reagents from CuAAC reactions of [small alpha]-fluoropropargyl benzothiazole sulfone with azides, react with aldehydes and ketones to give N-substituted 4-(1-fluorovinyl)triazoles. Reactions of aldehydes can be tuned towards E or Z-alkenes selectively.
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Stereoselective synthesis of fluorinated aminoglycosyl phosphonates

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1317-1321
DOI: 10.1039/C4OB02317J, CommunicationSanne Bouwman, Romano V. A. Orru, Eelco Ruijter
We report the highly stereoselective addition of lithiated difluorophosphonates to nitroglycals, providing synthetic access to biologically relevant fluorinated aminoglycosyl phosphonates.
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Synthesis and antimalarial evaluation of amide and urea derivatives based on the thiaplakortone A natural product scaffold

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1558-1570
DOI: 10.1039/C4OB01849D, PaperBrett D. Schwartz, Tina S. Skinner-Adams, Katherine T. Andrews, Mark J. Coster, Michael D. Edstein, Donna MacKenzie, Susan A. Charman, Maria Koltun, Scott Blundell, Anna Campbell, Rebecca H. Pouwer, Ronald J. Quinn, Karren D. Beattie, Peter C. Healy, Rohan A. Davis
A series of amide and urea analogues based on the thiaplakortone A natural product scaffold were synthesised and screened for in vitro antimalarial activity.
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Linear dialdehydes as promising substrates for aminocatalyzed transformations

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1280-1293
DOI: 10.1039/C4OB01805B, Review ArticleIndresh Kumar, Panduga Ramaraju, Nisar A. Mir, Anoop Singh
Linear dialdehydes: This article summarizes the recent utilization of linear dialdehydes as appropriate substrates for amine catalyzed cascade/domino transformations.
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Synthesis and antitumor activity of novel 2-substituted indoline imidazolium salt derivatives

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1550-1557
DOI: 10.1039/C4OB02385D, PaperXiao-Liang Xu, Chun-Lei Yu, Wen Chen, Ying-Chao Li, Li-Juan Yang, Yan Li, Hong-Bin Zhang, Xiao-Dong Yang
A series of novel 2-substituted indoline imidazolium salt derivatives were synthesized and their antitumor structure-activity relationship studies were reported.
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N-heterocyclic carbene-catalyzed cyclocondensation of 2-aryl carboxylic acids and enones: highly enantioselective synthesis of [small delta]-lactones

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1313-1316
DOI: 10.1039/C4OB02330G, CommunicationJin-Tang Cheng, Xiang-Yu Chen, Song Ye
The NHC-catalyzed [4 + 2] cyclocondensation of 2-aryl carboxylic acids with enones was developed, giving [small delta]-lactones in good yields with high enantioselectivities.
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Pd-catalyzed Heck-conjoined amidation and concomitant chemoselective Michael-addition: an efficient tandem approach to highly functionalized tetrahydroquinazolines from o-haloanilines

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1521-1530
DOI: 10.1039/C4OB02286F, PaperRakesh K. Saunthwal, Monika Patel, Abhinandan K. Danodia, Akhilesh K. Verma
Efficient palladium-catalyzed tandem approach for the synthesis of highly functionalized tetrahydroquinazolines from o-haloanilines with acrylates and isothiocyanates/isocyanates via Heck-conjoined amidation/thioamidation and concomitant chemoselective Michael-addition is described.
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