Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Friedel-Crafts alkylations of electron-rich aromatics with 3-hydroxy-2-oxindoles: scope and limitations

8 October, 2014 - 05:17

Org. Biomol. Chem., 2014, 12,8152-8173
DOI: 10.1039/C4OB01264J, PaperLakshmana K. Kinthada, Santanu Ghosh, K. Naresh Babu, Mohd. Sharique, Soumava Biswas, Alakesh Bisai
Lewis acid-catalyzed activation of 3-hydroxy-2-oxindoles +/-5 followed by reactions with various electron-rich aromatics was investigated. A variety of products were synthesized in high yields.
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A one-pot multicomponent coupling/cyclization for natural product herbicide (+/-)-thaxtomin A

8 October, 2014 - 05:17

Org. Biomol. Chem., 2014, 12,8125-8127
DOI: 10.1039/C4OB01148A, CommunicationJean Paul Bourgault, Amarendar Reddy Maddirala, Peter R. Andreana
The herbicide (+/-)-thaxtomin A has been synthesized in a one-pot two step process through an Ugi reaction followed by base-mediated cyclization.
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Convergent chemoenzymatic synthesis of a library of glycosylated analogues of pramlintide: structure-activity relationships for amylin receptor agonism

8 October, 2014 - 05:17

Org. Biomol. Chem., 2014, 12,8142-8151
DOI: 10.1039/C4OB01208A, PaperRenata Kowalczyk, Margaret A. Brimble, Yusuke Tomabechi, Antony J. Fairbanks, Madeleine Fletcher, Debbie L. Hay
The synthesis of a library of N-glycosylated pramlintide analogues to establish the SAR of amylin receptor agonism has been undertaken.
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Water-soluble NHC-Cu catalysts: applications in click chemistry, bioconjugation and mechanistic analysis

6 October, 2014 - 04:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01350F, PaperHeriberto Diaz Velazquez, Yara Ruiz Garcia, Matthias Vandichel, Annemieke Madder, Francis Verpoort
A series of novel bis(NHC) Cu(I) catalysts enables the production of triazoles with different substitution patterns and bioconjugation via "click" chemistry under homogeneous and/or heterogeneous catalytic conditions in aqueous media.
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Synthesis of 3-benzylisoquinolines by domino imination/cycloisomerisation of 2-propargylbenzaldehydes

2 October, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,8019-8030
DOI: 10.1039/C4OB01583E, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.Monica Dell'Acqua, Valentina Pirovano, Giorgio Confalonieri, Antonio Arcadi, Elisabetta Rossi, Giorgio Abbiati
A modular entry to 2-propargylbenzaldehydes and their use in [small mu ]W-promoted cascade reaction with ammonium acetate for the synthesis of 3-benzylisoquinolines.
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Asymmetric synthesis of (3S,1[prime or minute]S)-3-(1-amino-2,2,2-trifluoroethyl)-1-(alkyl)-indolin-2-one derivatives by addition of (S)-N-t-butylsulfinyl-3,3,3-trifluoroacetaldimine to 1-(alkyl)-indolin-2-ones

2 October, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,7909-7913
DOI: 10.1039/C4OB01453G, CommunicationPing Qian, Chen Xie, Lingmin Wu, Haibo Mei, Vadim A. Soloshonok, Jianlin Han, Yi Pan
This paper for the first time presents the addition reactions between amide-derived nucleophiles and CF3-containing N-sulfinyl-imines, with synthetically useful diastereoselectivity and chemical yields.
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Anion effects to deliver enhanced iridium catalysts for hydrogen isotope exchange processes

2 October, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,7927-7931
DOI: 10.1039/C4OB01570C, CommunicationAlan R. Kennedy, William J. Kerr, Rory Moir, Marc Reid
Enhanced catalyst efficiency and solvent applicability has been achieved for hydrogen isotope exchange processes with Ir(I) complexes possessing larger, more weakly coordinating counterions.
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Synthesis and photophysical properties of pyrene-based green fluorescent dyes: butterfly-shaped architectures

2 October, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,7914-7918
DOI: 10.1039/C4OB01509F, CommunicationDevendar Goud Vanga, Mithun Santra, Ashok Keerthi, Suresh Valiyaveettil
A few pyrene-based fluorescent compounds were synthesized using Pd/Cu-catalyzed cross-coupling reaction.
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Synthesis of phenanthridine derivatives via cascade annulation of diaryliodonium salts and nitriles

2 October, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,7904-7908
DOI: 10.1039/C4OB01504E, CommunicationJian Li, Hongni Wang, Jiangtao Sun, Yang Yang, Li Liu
A cascade coupling reaction of diaryliodonium salts and nitriles via copper-catalysis toward phenanthridine derivatives has been developed.
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Estimating the shape and size of supramolecular assemblies by variable temperature diffusion ordered spectroscopy

2 October, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,7932-7936
DOI: 10.1039/C4OB01373E, CommunicationBenjamin M. Schulze, Davita L. Watkins, Jing Zhang, Ion Ghiviriga, Ronald K. Castellano
Reported is characterization of the self-assembly of [small pi]-conjugated oligomers, molecules studied recently in photovoltaic devices, using variable temperature diffusion ordered spectroscopy; the approach has allowed estimation of assembly size, shape, and molecularity.
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Catalytic asymmetric synthesis of the pentacyclic core of (-)-nakadomarin A via oxazolidine as an iminium cation equivalent

2 October, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,7919-7922
DOI: 10.1039/C4OB01678E, CommunicationNobuya Tsuji, Michael Stadler, Naoya Kazumi, Tsubasa Inokuma, Yusuke Kobayashi, Yoshiji Takemoto
A catalytic asymmetric synthesis of the pentacyclic core of (-)-nakadomarin A was achieved.
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Synthesis of meta and para-substituted aromatic sulfonate derivatives of polydentate phenylazaphosphinate ligands: enhancement of the water solubility of emissive europium(III) EuroTracker[registered sign] dyes

2 October, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,8061-8071
DOI: 10.1039/C4OB01143K, PaperMartina Delbianco, Laurent Lamarque, David Parker
The use of a trifluoroethyl ester group to protect sulfonic acid moieties is used in the synthesis of a short series of water-soluble, very bright europium(III) complexes.
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Zinc mediated activation of terminal alkynes: stereoselective synthesis of alkynyl glycosides

2 October, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,7900-7903
DOI: 10.1039/C4OB01405G, CommunicationMadhu Babu Tatina, Anil Kumar Kusunuru, Syed Khalid Yousuf, Debaraj Mukherjee
Zinc mediated alkynylation reaction was studied for the preparation of C-glycosides from unactivated aromatic and aliphatic acetylenes. Different glycosyl donors such as glycals and anomeric acetates were tested towards in situ generated alkynyl zinc reagent using zinc dust and ethyl bromoacetate. The method provides a simple, mild and stereoselective access of alkynyl glycosides.
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Conformational effects due to stereochemistry and C3-substituents in xylopyranoside derivatives as studied by NMR spectroscopy

2 October, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,8031-8035
DOI: 10.1039/C4OB01422G, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Jerk Ronnols, Sophie Manner, Ulf Ellervik, Goran Widmalm
Dynamic NMR spectroscopy revealed an unequally populated equilibrium at low temperature for a 3-deoxygenated compound.
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The importance of chain conformational mobility during 5-exo-cyclizations of C-, N- and O-centred radicals

2 October, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,7983-7992
DOI: 10.1039/C4OB01419G, PaperJohn C. Walton
The access angle of a radical centre to an alkene acceptor was found to be a key parameter that pinpointed difficult chain reorganizations as responsible for the slow 5-exo cyclizations of N-centred radicals.
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The coumarin-pterocarpan conjugate - a natural product inspired hybrid molecular probe for DNA recognition

2 October, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,8087-8093
DOI: 10.1039/C4OB01360C, PaperShital K. Chattopadhyay, Indranil Kundu, Ratnava Maitra
Thermally induced cascade sigmatropic rearrangement of a butynyloxycoumarin derivative has led to a quick access to the coumarin-pterocarpan hybrid molecule. Biophysical studies together with molecular modeling show that this nature-inspired hybrid molecule is capable of binding to the minor groove of DNA as a non-conventional entity.
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Short and efficient synthesis of fluorinated [small delta]-lactams

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01547A, PaperThomas J. Cogswell, Craig S. Donald, De-Liang Long, Rodolfo Marquez
The diastereoselective synthesis of fluorinated [small delta]-lactams.
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A Lewis acid-mediated conformational switch

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, 12,7937-7941
DOI: 10.1039/C4OB01556H, PaperPeter C. Knipe, Hannah Lingard, Ian M. Jones, Sam Thompson, Andrew D. Hamilton
An isonicotinamide-substituted diphenylacetylene undergoes conformational switching upon recognition of Lewis acids.
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Neither azeotropic drying, nor base nor other additives: a minimalist approach to 18F-labeling

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, 12,8094-8099
DOI: 10.1039/C4OB01336K, PaperR. Richarz, P. Krapf, F. Zarrad, E. A. Urusova, B. Neumaier, B. D. Zlatopolskiy
A novel radiofluorination procedure using only precursor and [18F]fluoride without the need for azeotropic drying, base and other ingredients was developed.
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The origin of exo-stereoselectivity of norbornene in hetero Diels-Alder reactions

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, 12,8079-8086
DOI: 10.1039/C4OB01217H, PaperSesil Agopcan Cinar, Selami Ercan, Sule Erol Gunal, Ilknur Dogan, Viktorya Aviyente
The distortion of norbornene and the steric effect of the quasi-eclipsing forming bonds in the endo transition structures were demonstrated successfully in order to highlight the exo selectivity of norbornene in the reaction of 5-benzylidine-2-arylimino-3-aryl-thiazolidine-4-thiones with norbornene with the M06-2X/6-31+G(d)//B3LYP/6-31+G(d) methodology.
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