European Journal of Organic Chemistry

Cover image for Vol. 2012 Issue 28

October 2012

Volume 2012, Issue 28

Pages 5411–5617

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. You have free access to this content
      SupraBox: Chiral Supramolecular Oxazoline Ligands (Eur. J. Org. Chem. 28/2012)

      Marco Durini, Eleonora Russotto, Luca Pignataro, Oliver Reiser and Umberto Piarulli

      Article first published online: 18 SEP 2012 | DOI: 10.1002/ejoc.201290075

      Thumbnail image of graphical abstract

      The cover picture shows a copper complex of the SupraBox ligands. These ligands feature a chiral oxazoline ring and a urea functionality linked by a spacer and are able to form supramolecular bidentate assemblies that are held together by hydrogen bonds between the two urea moieties. The efficacy of the resulting copper complex as a chiral catalyst in asymmetric acylation reactions is enhanced by these cooperative effects, just as it happened with the collaboration between the two research groups in Como and Regensburg who developed this work. Details are discussed in the article by O. Reiser, U. Piarulli et al. on p. 5451 ff.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Graphical Abstract: Eur. J. Org. Chem. 28/2012 (pages 5411–5416)

      Article first published online: 18 SEP 2012 | DOI: 10.1002/ejoc.201290077

  3. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
  4. Microreview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. β-Amino Thiol Synthesis

      Synthetic Methodologies for the Preparation of β-Amino Thiols (pages 5423–5434)

      Guillaume Mercey, Vincent Reboul, Mihaela Gulea, Jocelyne Levillain and Annie-Claude Gaumont

      Article first published online: 6 JUN 2012 | DOI: 10.1002/ejoc.201200347

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      A practical method for the preparation of β-amino thiols is presented. This important class of compounds has various applications in many areas of chemistry. The present review reveals efficient and general methods for their synthesis reported in the literature, as well as the variety of accessible structures.

  5. Short Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Diversity-Oriented Synthesis

      Diversity-Oriented Synthesis of Spiro- and Fused Azacycles from Ketone Molecular Templates (pages 5435–5439)

      René Maltais and Donald Poirier

      Article first published online: 17 AUG 2012 | DOI: 10.1002/ejoc.201200852

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      A new diversity-oriented synthesis (DOS) methodology was developed to generate different azacycles from β-amino diols obtained from ketones. Considering the large number of natural products and synthetic templates bearing a ketone functionality, this DOS methodology opens the door to the exploration of chemical space regions around the ketone and will favor the discovery of bioactive compounds.

    2. Polycycles

      Synthesis of Indeno[1,2-b]indole Derivatives through One-Pot Sequential or Two-Step Iodine-Catalyzed C–O Activation and Palladium-Catalyzed C–H Functionalization (pages 5440–5445)

      Hai-Yan Xu, Xiao-Ping Xu, Shun-Yi Wang and Shun-Jun Ji

      Article first published online: 29 AUG 2012 | DOI: 10.1002/ejoc.201200876

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      An efficient route for the synthesis of indeno[1,2-b]indoles as tetracyclic derivatives of indole bearing 2-oxo-1-pyrrolidine moieties through one-pot sequential or two-step iodine-catalyzed C–O activation and palladium-catalyzed C–H functionalization is reported.

    3. Multicomponent Reactions

      One-Pot, Three-Component Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles Starting from Primary Alcohols (pages 5446–5449)

      Guanyi Jin, Jian Zhang, Dan Fu, Jingjing Wu and Song Cao

      Article first published online: 16 AUG 2012 | DOI: 10.1002/ejoc.201200830

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      A series of 1,4,5-trisubstituted 1,2,3-triazoles was synthesized through the cycloaddition of a wide range of primary alcohols with sodium azide and active methylene ketones in the presence of N-(p-toluenesulfonyl)imidazole (TsIm), tetrabutylammonium iodide (TBAI), and triethylamine (TEA) by using a mixed DMF/DMSO solvent system.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Supramolecular Catalysts

      SupraBox: Chiral Supramolecular Oxazoline Ligands (pages 5451–5461)

      Marco Durini, Eleonora Russotto, Luca Pignataro, Oliver Reiser and Umberto Piarulli

      Article first published online: 10 JUL 2012 | DOI: 10.1002/ejoc.201200516

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      SupraBox ligands feature a chiral oxazoline ring and a urea functionality linked by a spacer and form supramolecular bidentate assemblies when coordinated to a metal. A small SupraBox library was prepared and tested in the kinetic resolution of racemic hydrobenzoin and the desymmetrization of meso-hydrobenzoin by copper-catalyzed benzoylation.

    2. Click Chemistry

      Discovery of a Robust and Efficient Homogeneous Silver(I) Catalyst for the Cycloaddition of Azides onto Terminal Alkynes (pages 5462–5470)

      James McNulty and Kunal Keskar

      Article first published online: 17 AUG 2012 | DOI: 10.1002/ejoc.201200930

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      A highly efficient, chemically stable, and well-defined homogeneous silver(I) catalyst is reported for the cycloaddition of azides onto terminal alkynes (Ag-AAC reaction).

    3. Natural Products

      Structure and Absolute Stereochemistry of Nortriterpenoids from Schisandra chinensis (Turcz.) Baill (pages 5471–5482)

      Jian-Rong Wang, Tibor Kurtán, Attila Mándi and Yue-Wei Guo

      Article first published online: 15 AUG 2012 | DOI: 10.1002/ejoc.201200557

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      Thirteen Schisandra nortriterpenoids, two of them possessing unprecedented skeletons, were isolated from the Chinese medicinal plant Schisandra chinensis. Their absolute configurations were determined by means of time-dependent density functional theory electronic circular dichroism calculations.

    4. Nucleoside Sugar Conformation

      CAL-B-Catalyzed Acylation of Nucleosides and Role of the Sugar Conformation: An Improved Understanding of the Enzyme-Substrate Recognition (pages 5483–5490)

      Saúl Martínez-Montero, Susana Fernández, Yogesh S. Sanghvi, Vicente Gotor and Miguel Ferrero

      Article first published online: 23 AUG 2012 | DOI: 10.1002/ejoc.201200609

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      The sugar conformation of nucleosides plays a critical role in Candida antarctica lipase B catalyzed acylation. Specifically, the North nucleoside sugar ring conformation is preferred for efficient binding at the catalytic site. Nuclear magnetic resonance spectroscopy was used to establish the sugar conformation, which was confirmed by molecular modeling studies.

    5. Asymmetric Synthesis

      Stereoselective Synthesis of cis-1,3-Dimethyltetrahydroisoquinolines: Formal Synthesis of Naphthylisoquinoline Alkaloids (pages 5491–5497)

      Mercedes Amat, Fabiana Subrizi, Viviane Elias, Núria Llor, Elies Molins and Joan Bosch

      Article first published online: 15 AUG 2012 | DOI: 10.1002/ejoc.201200798

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      An efficient stereoselective synthesis of enantiopure cis-1,3-dimethyltetrahydroisoquinolines 9, synthetic precursors of naphthylisoquinoline alkaloids, from an easily accessible phenylglycinol-derived tricyclic lactam 2 is reported.

    6. Enzyme Inhibitors

      Combined Chemical, Biological and Theoretical DFT-QTAIM Study of Potent Glycosidase Inhibitors Based on Quaternary Indolizinium Salts (pages 5498–5514)

      Peter Šafář, Jozefína Žúžiová, Štefan Marchalín, Nadežda Prónayová, Ľubomír Švorc, Viktor Vrábel, Sergej Šesták, Dubravko Rendić, Vincent Tognetti, Laurent Joubert and Adam Daïch

      Article first published online: 15 AUG 2012 | DOI: 10.1002/ejoc.201200431

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      Six novel enantiopure indolizidinediols have been synthesized with regioselective THF ring opening as a key step. These substrates and others were then quaternized. The stereochemistry of these reactions was elucidated by NMR, X-ray diffraction, and a combined DFT-QTAIM study. Inhibitory assays were performed with six indolizidines and two derivatives exhibited pH-dependent inhibition of dGMIIb.

    7. Chemoselective Cyclization

      Controlled Switching of Multicomponent Heterocyclizations of 5-Amino-N-arylpyrazole-4-carboxamides, 1,3-Cyclohexanediones, and Aldehydes (pages 5515–5524)

      Valentin A. Chebanov, Vyacheslav E. Saraev, Svetlana V. Shishkina, Oleg V. Shishkin, Vladimir I. Musatov and Sergey M. Desenko

      Article first published online: 15 AUG 2012 | DOI: 10.1002/ejoc.201200669

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      The multicomponent heterocyclization of5-amino-N-arylpyrazole-4-carboxamides,1,3-cyclohexanediones, and aldehydes was switched between pyrazolo[5,1-b]- and pyrazolo[1,5-a]-quinazolines by changing the reaction parameters. An unusual third pathway leading to the formation of 5-acridin-10-yl-pyrazole-4-carboxamideswith hindered rotation of the pyrazole moiety around the C–N bond was also found.

    8. Heterogeneous Catalysis

      Practical Pd/C-Catalysed Suzuki–Miyaura Reactions for the Preparation of 3-Aryl-4-oxypyridin-2(1H)-ones, 3-Aryl-2,4-oxypyridines and 3-Aryl-2,4-oxyquinolines as Useful Intermediates for the Synthesis of Biologically Active Compounds (pages 5525–5533)

      Marc Lamblin, Hugo Bares, Jean Dessolin, Christel Marty, Nathalie Bourgougnon and François-Xavier Felpin

      Article first published online: 23 AUG 2012 | DOI: 10.1002/ejoc.201200721

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      A heterogeneous Pd/C-catalysed Suzuki–Miyaura cross-coupling reaction for the preparation of 3-aryl-4-oxypyridin-2(1H)-ones, 3-aryl-2,4-oxypyridines, and 3-aryl-2,4-oxyquinolines represents a useful and efficient alternative to homogeneous conditions. These interesting heterocycles can be used as platforms for the synthesis of biologically active compounds.

    9. Conformation Analysis

      Conformational Constraints: Nature Does It Best with Sialyl Lewisx (pages 5534–5539)

      Alexander Titz, Alberto Marra, Brian Cutting, Martin Smieško, George Papandreou, Alessandro Dondoni and Beat Ernst

      Article first published online: 20 AUG 2012 | DOI: 10.1002/ejoc.201200744

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      To facilitate the interaction under the shear stress conditions in the blood vessel, the conformation of sLex is stabilized via lipophilic inter-residual contacts. The methyl group in fucose is optimally suited to stabilize the sLex core through an interaction with the galactose moiety.

    10. C–H Arylation

      Palladium-Catalyzed Direct C–H Arylation of Thieno[3,4-b]pyrazines: Synthesis of Advanced Oligomeric and Polymeric Materials (pages 5540–5551)

      Nabiha I. Abdo, Ashraf A. El-Shehawy, Ahmed A. El-Barbary and Jae-Suk Lee

      Article first published online: 23 AUG 2012 | DOI: 10.1002/ejoc.201200769

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      Regioselective C–H arylation of thieno[3,4-b]pyrazine derivatives with heteroaryl bromides under “Heck-type” conditions gives donor–acceptor π-conjugated oligomeric and copolymeric materials in a facial manner. The thienopyrazine unit altered the photophysical and electrochemical properties. Diffraction peaks indicate interchain spacing similar to P3HT and suggest π-π stacking of the backbones.

    11. Synthesis of Alkylarenes

      Regioselective Synthesis of Alkylarenes by Two-Step ipso-Substitution of Aromatic Dicarboxylic Acids (pages 5552–5563)

      Andrea Bramborg and Torsten Linker

      Article first published online: 16 AUG 2012 | DOI: 10.1002/ejoc.201200823

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      The transformation from acid to alkyl groups is the result of a simple two-step sequence that allows the regioselective synthesis of substituted benzenes and naphthalenes 4 or 5 from inexpensive terephthalic acid or naphthalene-1,4-dicarboxylic acid1 in high yields. The formation of intermediates 2 and 3 is interesting in the context of the mechanism of the Birch reduction, and the rearomatizations proceed by different reaction pathways.

    12. Hydroamination of Alkynes

      Gallium Trichloride Catalyzed Hydroamination of Alkynes: Scope, Limitation, and Mechanistic Studies by DFT (pages 5564–5572)

      Lei Li, Genping Huang, Zhou Chen, Wei Liu, Xiufang Wang, Yanmei Chen, Lijuan Yang, Wu Li and Yahong Li

      Article first published online: 21 AUG 2012 | DOI: 10.1002/ejoc.201200829

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      The hydroamination of alkynes with aromatic amines catalyzed by gallium trichloride is presented. Markovnikov products were exclusively obtained with most of the aniline derivatives. The reaction mechanism was investigated by DFT calculations. The regioselectivities of the reactions as well as the reactivities of the different amine substrates are well explained by the proposed mechanism.

    13. Asymmetric Catalysis

      Asymmetric Ion-Pairing Catalysis of the Reversible Cyclization of 2′-Hydroxychalcone to Flavanone: Asymmetric Catalysis of an Equilibrating Reaction (pages 5573–5584)

      Lukas Hintermann and Claudia Dittmer

      Article first published online: 23 AUG 2012 | DOI: 10.1002/ejoc.201200838

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      The cyclization of nonactivated 2′-hydroxychalcones to flavanones has been realized for the first time with asymmetric induction. In spite of the reversibility of the reactions, this ion-pairing catalysis reaches intrinsic enantioselectivities of up to S = 14.4 (er = 93.5:6.5) and illustrates the characteristic behavior of reversible asymmetric catalyses close to their equilibria.

    14. Sequential Synthesis

      Three-Component, One-Pot Sequential Synthesis of Tetracyclic Pyrido[2′,1′:2,3]imidazo[5,1-a]isoquinolinium Compounds as Potent Anticancer Agents (pages 5585–5594)

      Huayong Zhou, Wei Wang, Oleg Khorev, Yongliang Zhang, Zehong Miao, Tao Meng and Jingkang Shen

      Article first published online: 17 AUG 2012 | DOI: 10.1002/ejoc.201200542

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      A convenient and efficient one-pot synthesis of diversely substituted pyrido[2′,1′:2,3]imidazo[5,1-a]isoquinolinium compounds catalyzed by ytterbium triflate and silver triflate was developed. A few compounds showed strong cytotoxicity against HeLa cells.

    15. Cross-Coupling Reaction

      One-Pot Chemoselective Bis(Suzuki–Miyaura Cross-Coupling): Efficient Access to 3,9-Bis[(hetero)aryl]-4H-pyrido[1,2-a]pyrimidin-4-one Derivatives Under Microwave Irradiation (pages 5595–5604)

      Youssef Kabri, Maxime D. Crozet, Nicolas Primas and Patrice Vanelle

      Article first published online: 23 AUG 2012 | DOI: 10.1002/ejoc.201200748

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      A one-pot chemoselective bis(Suzuki–Miyaura cross-coupling) reaction under microwave irradiation is reported for the 4H-pyrido[1,2-a]pyrimidin-4-one series. This reaction procedure allowed us to substitute successively at the 3- and then at the 9-position of (7,9-dichloro-3-iodo-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)methylacetate (4) with various boronic acids.

    16. Porphyrinoid Multichromophores

      Corrole–Porphyrin Conjugates with Interchangeable Metal Centers (pages 5605–5617)

      Thien H. Ngo, Francesco Nastasi, Fausto Puntoriero, Sebastiano Campagna, Wim Dehaen and Wouter Maes

      Article first published online: 13 AUG 2012 | DOI: 10.1002/ejoc.201200836

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      Corrole–porphyrin multichromophoric systems containing a variety of (readily exchangeable) metals in the tetrapyrrolic ligands have been successfully synthesized starting from a versatile meso-pyrimidinylcorrole scaffold. Although the conjugates show only weak interchromophoric electronic interactions, fast and efficient corrole-to-porphyrin singlet–singlet energy transfer was observed.

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