European Journal of Organic Chemistry

Cover image for Vol. 2009 Issue 9

March 2009

Volume 2009, Issue 9

Pages 1283–1452

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Complexation Behavior of a Supramolecular Organic Fluorophore Prepared by Solid-State Co-Grinding Crystallization Using 2-Anthracenecarboxylic Acid and (R)-1-(2-Naphthyl)ethylamine and Its Optical Properties (Eur. J. Org. Chem. 9/2009) (page 1283)

      Yoshitane Imai, Katuzo Murata, Kakuhiro Kawaguchi, Takunori Harada, Yoko Nakano, Tomohiro Sato, Michiya Fujiki, Reiko Kuroda and Yoshio Matsubara

      Article first published online: 2 MAR 2009 | DOI: 10.1002/ejoc.200990018

  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. 9/2009 (pages 1283–1289)

      Article first published online: 2 MAR 2009 | DOI: 10.1002/ejoc.200990020

  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. Trifunctional Cyclodextrins

      Cap-Assisted Synthesis of Hetero-Trifunctional Cyclodextrins, from Flamingo Cap to Bascule Bridge (pages 1295–1303)

      Matthieu Sollogoub

      Article first published online: 13 FEB 2009 | DOI: 10.1002/ejoc.200800930

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      In this review we focus on the synthesis of cyclodextrins bearing three different functionalities by capping strategies. Thesehetero-trifunctional cyclodextrins were first prepared as mixtures; recent methods allow their efficient synthesis as pure compounds.

  5. Short Communications

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

      Cyclohexane-1,2-diamines: Efficient Catalysts for the Enantioselective Conjugate Addition of Ketones to Nitro Olefins (pages 1305–1308)

      Ramesh Rasappan and Oliver Reiser

      Article first published online: 3 FEB 2009 | DOI: 10.1002/ejoc.200801263

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      Highly enantioselective conjugate addition of ketons to nitro olefines were carried out with simple primary amine organocatalysts. A pathway for catalyst deactivation by irreversible pyrrole formation was identified.

    2. Application of 7-endo-trig Pictet–Spengler Cyclization to the Formation of the Benzazepine Ring: Synthesis of Benzazepinoindoles (pages 1309–1312)

      Sudhir K. Sharma, Sunil Sharma, Piyush K. Agarwal and Bijoy Kundu

      Article first published online: 13 FEB 2009 | DOI: 10.1002/ejoc.200801201

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      The preparation of benzazepinoindoles, fused heterocycles with a benzazepinemoiety, was accomplished through an intramolecular 7-endo-trig Pictet–Spengler cyclization.

    3. Geminal Oxyarylation of Alkenes

      Palladium-Catalyzed Three-Component Coupling Reactions: 1,1-Difunctionalization of Activated Alkenes (pages 1313–1316)

      Arantxa Rodriguez and Wesley J. Moran

      Article first published online: 22 JAN 2009 | DOI: 10.1002/ejoc.200801245

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      The palladium-catalyzed formation of aldol-type products was achieved through a three-component coupling reaction.

    4. DKR of Secondary Alcohols

      Dicarbonylchloro(pentabenzylcyclopentadienyl)ruthenium as Racemization Catalyst in the Dynamic Kinetic Resolution of Secondary Alcohols (pages 1317–1320)

      Denys Mavrynsky, Mari Päiviö, Katri Lundell, Reijo Sillanpää, Liisa T. Kanerva and Reko Leino

      Article first published online: 3 FEB 2009 | DOI: 10.1002/ejoc.200801248

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      New half-sandwich complexes of ruthenium have been prepared and evaluated as racemization catalysts for the metalloenzymatic dynamic kinetic resolution (DKR) of secondary alcohols. The pentabenzyl-substituted ruthenium complex described herein shows excellent catalytic activity and stability under the employed reaction conditions with performance superior to that of the current lead catalyst with pentaphenyl ligand structure under similar reaction conditions.

    5. Flow Chemistry

      Continuous-Flow Microreactor Chemistry under High-Temperature/Pressure Conditions (pages 1321–1325)

      Tahseen Razzaq, Toma N. Glasnov and C. Oliver Kappe

      Article first published online: 13 FEB 2009 | DOI: 10.1002/ejoc.200900077

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      Translating microwave to flow chemistry: In a high-temperature/pressure microtubular flow device, many of the benefits inherent to microwave chemistry such as rapid heating/cooling and sealed-vessel processing can be mimicked, including the generation of solvents in their supercritical state. In addition, the scalability problem of microwave synthesis can be eliminated.

  6. Full Papers

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

      Continuous Flow Hydrogenation of Functionalized Pyridines (pages 1327–1334)

      Muhammed Irfan, Elena Petricci, Toma N. Glasnov, Maurizio Taddei and C. Oliver Kappe

      Article first published online: 3 FEB 2009 | DOI: 10.1002/ejoc.200801131

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      Substituted pyridines can be hydrogenated efficiently in a continuous flow approach by using a dedicated high temperature/pressure flow reactor and pre-packed catalyst cartridges. Good-to-excellent yields ofsubstituted piperidines are obtained by using Pd/C, Rh/C, or Pt/C as heterogeneous catalysts at temperatures of 60–80 °C and hydrogen pressures of 30–90 bar.

    2. Supramolecular Fluorophores

      Complexation Behavior of a Supramolecular Organic Fluorophore Prepared by Solid-State Co-Grinding Crystallization Using 2-Anthracenecarboxylic Acid and (R)-1-(2-Naphthyl)ethylamine and Its Optical Properties (pages 1335–1339)

      Yoshitane Imai, Katuzo Murata, Kakuhiro Kawaguchi, Takunori Harada, Yoko Nakano, Tomohiro Sato, Michiya Fujiki, Reiko Kuroda and Yoshio Matsubara

      Article first published online: 20 JAN 2009 | DOI: 10.1002/ejoc.200801158

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      A novel crystalline supramolecular organic fluorophore having a 21-helical columnar structure was prepared by the solid-state co-grinding crystallization technique. Although many organic fluorophores lose their fluorescence in the solid state, this supramolecular organic fluorophore exhibits fluorescence even in the solid state.

    3. Organocatalytic Pregabalin Synthesis

      A Simple Organocatalytic Enantioselective Synthesis of Pregabalin (pages 1340–1351)

      Oriol Bassas, Juhani Huuskonen, Kari Rissanen and Ari M. P. Koskinen

      Article first published online: 5 FEB 2009 | DOI: 10.1002/ejoc.200801220

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      A new organocatalytic procedure for Pregabalin (1) is reported.Michael addition of Meldrum's acid to nitroalkene 3 catalyzed by a quinidine-derived thiourea gave the key chiral intermediate nitroalkane (S)-4 inup to 75% ee, and two simple operations give pregabalin in high chemical yield. A family of novel thiourea catalysts with different substituents were prepared and evaluated.

    4. Mo-Catalyzed AAA

      Carbohydrate-Based Pyridine-2-carboxamides for Mo-Catalyzed Asymmetric Allylic Alkylations (pages 1352–1356)

      Raffaella Del Litto, Vincenzo Benessere, Francesco Ruffo and Christina Moberg

      Article first published online: 29 JAN 2009 | DOI: 10.1002/ejoc.200801240

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      Bis(pyridine-2-carboxamides) with their chirality derived from glucose serve as highly enantioselective ligands for microwave-mediated Mo-catalyzed asymmetric allylic alkylations (AAA) by using both linear and branched allylic carbonates.

    5. Cyclopropyl Amino Acids

      Methyl 2-(Benzyloxycarbonylamino)-2-cyclopropylideneacetate: A Versatile Building Block for Cyclopropyl-Containing Amino Acids (pages 1357–1364)

      Michael Limbach, Alexander Lygin, Mazen Es-Sayed and Armin de Meijere

      Article first published online: 5 FEB 2009 | DOI: 10.1002/ejoc.200800817

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      Methyl 2-(benzyloxycarbonylamino)-2-cyclopropylideneacetate, which has been prepared in nine steps (24 % yield) starting from L-serine, can be employed in various ways towards the syntheses of new cyclopropyl-containing amino acids.

    6. Core Oligosaccharides

      Structure of the Core Region from the Lipopolysaccharide of Plesiomonas shigelloides Strain 302-73 (Serotype O1) (pages 1365–1371)

      Giuseppina Pieretti, M. Michela Corsaro, Rosa Lanzetta, Michelangelo Parrilli, Silvia Vilches, Susana Merino and Juan M. Tomás

      Article first published online: 4 FEB 2009 | DOI: 10.1002/ejoc.200801200

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      The structure of the core oligosaccharide from Plesiomonas shigelloides 302-73 (serotype O1) was elucidated by 2D NMR spectroscopy and MALDI-TOF MS. It showed similarity to that of serotype O54 and O17 and is characterised by the presence of two α-GlcN-(1[RIGHTWARDS ARROW]4)-α-GalA disaccharides in the outer core and by the presence of D-glycero-D-talo-2-octulopyranosonic acid in the inner core.

    7. Asymmetric Homologation

      First Stereoselective Synthesis of (1R,2R,4R)- and (1S,2R,4S)-2-Substituted-1-azabicyclo[2.2.1]heptanes (pages 1372–1376)

      Pablo Etayo, Ramón Badorrey, María D. Díaz-de-Villegas and José A. Gálvez

      Article first published online: 6 FEB 2009 | DOI: 10.1002/ejoc.200801216

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      By choosing the appropriate methodology, enantiomerically pure (1R,2R,4R)- and(1S,2R,4S)-1-azabicyclo[2.2.1]heptanessubstituted at the 2-position can be obtained from a common precursor.

    8. Tautomerism of Purine Bases

      NMR Quantification of Tautomeric Populations in Biogenic Purine Bases (pages 1377–1383)

      Tomáš Bartl, Zuzana Zacharová, Pavlína Sečkářová, Erkki Kolehmainen and Radek Marek

      Article first published online: 11 FEB 2009 | DOI: 10.1002/ejoc.200801016

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      Low-temperature NMR spectroscopy has been used to characterize the tautomeric equilibria of a series of biogenic purine bases. The effect of substitution on the N(7)H/N(9)H ratio is discussed and themechanism for the tautomeric exchange is studied. The results indicate a significant role of supramolecular clusters in the proton transfer process.

    9. Improved Biocatalyst

      Coupling of Site-Directed Mutagenesis and Immobilization for the Rational Design of More Efficient Biocatalysts: The Case of Immobilized 3G3K PGA from E.coli (pages 1384–1389)

      Immacolata Serra, Davide A. Cecchini, Daniela Ubiali, Elena M. Manazza, Alessandra M. Albertini and Marco Terreni

      Article first published online: 3 FEB 2009 | DOI: 10.1002/ejoc.200801204

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      An investigation of the catalytic properties of the immobilized 3G3K mutant PGA obtained by site-directed mutagenesis is reported. The immobilized preparation on glyoxyl agarose showed the same behaviouras the free enzyme. Moreover, the mutant immobilized on glyoxyl agarose showed better synthetic performance than the commercial wild-type PGA.

    10. Trifluoromethylating Reagents

      Benchmark and Solvent-Free Preparation of Sulfonium Salt Based Electrophilic Trifluoromethylating Reagents (pages 1390–1397)

      Yohan Macé, Benoit Raymondeau, Charlotte Pradet, Jean-Claude Blazejewski and Emmanuel Magnier

      Article first published online: 4 FEB 2009 | DOI: 10.1002/ejoc.200801222

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      A multicomponent reaction for the easy preparation of trifluoromethylsulfonium salts is described. This simple procedure offers the opportunity to prepare a wide range of electrophilic trifluoromethylatingreagents. The variety and the chosen reactivity of the prepared compounds will therefore permit the rapid synthesis of the chosen reagent in accordance with the demands of the nucleophile.

    11. DNA Ligands

      Guanine-Containing DNA Minor-Groove Binders (pages 1398–1406)

      Daniel Pulido, Albert Sánchez, Jordi Robles, Enrique Pedroso and Anna Grandas

      Article first published online: 6 FEB 2009 | DOI: 10.1002/ejoc.200800892

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      The DNA-stabilizing properties of six dipyrrole-containing DNA ligands that combine (guanin-9-yl)acetyl, (guanin-7-yl)acetyl or acetyl moieties at the N terminus and two lysines or a (dimethylamino)propylgroup at the C terminus have been examined. The (dimethylamino)propyl tail and the (guanin-9-yl)acetyl moiety provided the highest affinity for DNA.

    12. Sesquiterpene Metabolites

      Novel Lactone Chamigrene-Derived Metabolites from Laurencia majuscula (pages 1407–1411)

      Ana R. Díaz-Marrero, Inmaculada Brito, José M. de la Rosa, Luis D'Croz, Oscar Fabelo, Catalina Ruiz-Pérez, José Darias and Mercedes Cueto

      Article first published online: 2 FEB 2009 | DOI: 10.1002/ejoc.200801006

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      The structures of gomerolactones A–D, isolated from Laurencia majuscula, were determined spectroscopically. The absolute configuration at the carbon ring closure of the γ- and δ-lactone of compounds 1 and 2, respectively, was determined by NMR spectroscopy with the use of Pirkle's reagent at low temperature. The absolute stereochemistry of compounds 3 and 4 was determined by X-ray analysis.

    13. Myrioneuron Alkaloids

      Novel Alkaloids from Myrioneuron nutans (pages 1412–1416)

      Van Cuong Pham, Akino Jossang, Thierry Sévenet, Van Hung Nguyen and Bernard Bodo

      Article first published online: 13 FEB 2009 | DOI: 10.1002/ejoc.200801028

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      Dehydronitraramine (1) and N-formylmyrionine (2) were isolated from the leaves of Myrioneuron nutans. The absolute configuration 8S,9R,10S of N-formylmyrionine (2) was established on the basis of the known (8S,9R,10S)-myrionine. Dehydronitraramine (1) displayed a moderate antiplasmodial activity against Plasmodiumfalciparum with an IC50 of 16 μM.

    14. Vicinal Oligoketone Chemistry

      The Smallest Vicinal Tricarbonyl Compound as a Monohydrate and Tetracarbonyl Compound as a Thiane Derivative – First Effective Synthesis, Characterization and Chemistry (pages 1417–1426)

      Shyamaprosad Goswami, Annada C. Maity, Hoong-Kun Fun and Suchada Chantrapromma

      Article first published online: 5 FEB 2009 | DOI: 10.1002/ejoc.200801050

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      An effective synthesis of 2-oxo-1,3-propanedial monohydrate or mesoxaldehyde and the first synthesis of 2,3-dioxo-1,4-butanedial as a thiane derivative are reported. Additionally, a one-step synthetic strategy to prepare a series of different biheterocycles with the smallest vicinal tetracarbonyl compound is demonstrated.

    15. Metabolites from Fungi

      Pseudoanguillosporin A and B: Two New Isochromans Isolated from the Endophytic Fungus Pseudoanguillospora sp. (pages 1427–1434)

      Ines Kock, Siegfried Draeger, Barbara Schulz, Brigitta Elsässer, Tibor Kurtán, Ágnes Kenéz, Sándor Antus, Gennaro Pescitelli, Piero Salvadori, John-Bryan Speakman, Joachim Rheinheimer and Karsten Krohn

      Article first published online: 4 FEB 2009 | DOI: 10.1002/ejoc.200801083

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      The structure of two new bioactive isochromans, pseudoanguillosporin A (2a) and B (3), was determined by NMR spectroscopy and the absolute configuration by a combination of CD spectroscopy, TDDFT CD calculations, and Mosher's NMR method. The axial chirality of 1 was assigned by exciton analysis of its CD spectrum and confirmed by ZINDO CD calculations.

    16. One-Pot Synthesis

      Highly Chemoselective Synthesis of 6-Alkoxy-1-alkyl(aryl)-3-trifluoroacetyl-1,4,5,6-tetrahydropyridines and 1-Alkyl(aryl)-6-amino-3-trifluoroacetyl-1,4,5,6-tetrahydropyridines (pages 1435–1444)

      Nilo Zanatta, Liana da S. Fernandes, Fabiane M. Nachtigall, Helena S. Coelho, Simone S. Amaral, Alex F. C. Flores, Helio G. Bonacorso and Marcos A. P. Martins

      Article first published online: 3 FEB 2009 | DOI: 10.1002/ejoc.200801119

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      Chemoselective control of the synthesisof 6-alkoxy-1-alkyl(aryl)-3-trifluoroacetyl-1,4,5,6-tetrahydropyridines and 1-Alkyl(aryl)-6-amino-3-trifluoracetyl-1,4,5,6-tetrahydropyridines.

    17. Chiral Ligands

      A Series of Novel N,N-Donor Ligands with Binaphthyl Backbones (pages 1445–1452)

      Thomas Jozak, Marcus Fischer, Johannes Thiel, Yu Sun, Harald Kelm and Werner R. Thiel

      Article first published online: 13 FEB 2009 | DOI: 10.1002/ejoc.200801224

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      Three novel azole-functionalized 1,1-binaphthyl derivatives have been synthesized from versatile starting materials.

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