European Journal of Organic Chemistry

Cover image for Vol. 2009 Issue 10

April 2009

Volume 2009, Issue 10

Pages 1460–1631

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Editorial Survey
    7. Microreview
    8. Short Communications
    9. Full Papers
    10. Correction
    1. Synthesis of the C11–C23 Fragment of the Potent Antitumor Agent Dictyostatin (Eur. J. Org. Chem. 10/2009) (page 1460)

      Luiz C. Dias, Dimas J. P. Lima, Caroline C. S. Gonçalves and Adriano D. Andricopulo

      Version of Record online: 13 MAR 2009 | DOI: 10.1002/ejoc.200990021

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Editorial Survey
    7. Microreview
    8. Short Communications
    9. Full Papers
    10. Correction
  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Editorial Survey
    7. Microreview
    8. Short Communications
    9. Full Papers
    10. Correction
  4. News

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Editorial Survey
    7. Microreview
    8. Short Communications
    9. Full Papers
    10. Correction
  5. Editorial Survey

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Editorial Survey
    7. Microreview
    8. Short Communications
    9. Full Papers
    10. Correction
  6. Microreview

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Editorial Survey
    7. Microreview
    8. Short Communications
    9. Full Papers
    10. Correction
    1. Total Synthesis

      Stereocontrolled Preparation of Fully Substituted Cyclopentanes: Relevance to Total Synthesis (pages 1477–1489)

      Brian Heasley

      Version of Record online: 11 FEB 2009 | DOI: 10.1002/ejoc.200801229

      Thumbnail image of graphical abstract

      A hexa-substituted chlorocyclopentane framework is common to a variety of dimeric marine alkaloids of the oroidin family. In the pursuit of synthons for oroidin dimers such as palau'amine, the stereocontrolled synthesis of complex C5 rings has seen a renaissance in recent years.Stereochemical challenges posed by these intricate and densely functionalized cyclopentanes will be discussed.

  7. Short Communications

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Editorial Survey
    7. Microreview
    8. Short Communications
    9. Full Papers
    10. Correction
    1. Antitumor Agents

      Synthesis of the C11–C23 Fragment of the Potent Antitumor Agent Dictyostatin (pages 1491–1494)

      Luiz C. Dias, Dimas J. P. Lima, Caroline C. S. Gonçalves and Adriano D. Andricopulo

      Version of Record online: 13 FEB 2009 | DOI: 10.1002/ejoc.200801234

      Thumbnail image of graphical abstract

      The synthesis of the C11–C23 fragment of dictyostatin proceeded in good overall yield after 15 steps for the longest linear sequence.

    2. Tetrazolyl Synthons

      A Tetrakis(tetrazolyl) Analogue of EDTA (pages 1495–1498)

      Faycal Touti, Philippe Maurin and Jens Hasserodt

      Version of Record online: 23 FEB 2009 | DOI: 10.1002/ejoc.200900016

      Thumbnail image of graphical abstract

      A synthon for the convergent introduction of a protected tetrazole moiety intonucleophile-bearing molecules is presented. Benzyl deprotection is accomplished under neutral conditions. The usual in situ establishment of the tetrazole moiety is thusavoided, as is the lack of regioselective control during subsequent protection. The exemplary synthesis of a new isoelectronic analogue of EDTA is presented.

    3. HOBt Replacements

      Synthesis and Application of N-Hydroxylamine Derivatives as Potential Replacements for HOBt (pages 1499–1501)

      Ayman El-Faham and Fernando Albericio

      Version of Record online: 18 FEB 2009 | DOI: 10.1002/ejoc.200801179

      Thumbnail image of graphical abstract

      Cheap and convenient replacement additives for the explosive HOBt are reported to be used in peptide synthesis.

    4. One-Pot Reactions

      One-Pot, Selective Hydroformylation, Condensation, and Hydrogenation Processes by a Sol–Gel Entrapped Rhodium Complex, an Immobilized Base, and an Ionic Liquid (pages 1502–1505)

      Khalil Hamza, Herbert Schumann and Jochanan Blum

      Version of Record online: 4 MAR 2009 | DOI: 10.1002/ejoc.200801258

      Thumbnail image of graphical abstract

      In the presence of [Rh(cod)Cl]2 that has been entrapped within an ionic liquid confined silica sol–gel, styrene derivatives were hydroformylated at 80° C to selectively give branched aldehydes that undergo, withinthe same pot, condensation with active methylene compounds followed by hydrogenation of the resulting unsaturated products.

    5. Synthetic Methods

      Cascade Annulation Reactions To Access the Structural Cores of Stereochemically Unusual Strychnos Alkaloids (pages 1506–1510)

      Ricardo Delgado and Simon B. Blakey

      Version of Record online: 4 MAR 2009 | DOI: 10.1002/ejoc.200900033

      Thumbnail image of graphical abstract

      A versatile cascade sequence providesrapid access to the core structure of the stereochemically unusual Malagashaninealkaloids. Amide reduction provides access to particularly sensitive iminium ions, facilitating this cascade process.

    6. Dynamic Covalent Chemistry

      Preparation of a Reversible Redox-Controlled Cage-Type Molecule Linked by Disulfide Bonds (pages 1511–1514)

      Yih-Chern Horng, Tzung-Lung Lin, Cheng-Yi Tu, Ting-Ju Sung, Chang-Chih Hsieh, Ching-Han Hu, Hon Man Lee and Ting-Shen Kuo

      Version of Record online: 17 FEB 2009 | DOI: 10.1002/ejoc.200900044

      Thumbnail image of graphical abstract

      A trithiol macromolecule, comprising an intrinsic conformational propensity for dimerization (molecular capsule) as opposed to oligomerization upon oxidation, was effortlessly prepared through rational design.The X-ray structure of the molecular capsule represents the first successful example of a redox-controlled reversible dimeric capsule linked through covalent disulfide bonds.

  8. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Editorial Survey
    7. Microreview
    8. Short Communications
    9. Full Papers
    10. Correction
    1. Fluorescent Nucleoside Analogues

      Synthesis and Photophysical Characterisation of Fluorescent 8-(1H-1,2,3-Triazol-4-yl)adenosine Derivatives (pages 1515–1521)

      Christine Dyrager, Karl Börjesson, Peter Dinér, Annelie Elf, Bo Albinsson, L. Marcus Wilhelmsson and Morten Grøtli

      Version of Record online: 11 FEB 2009 | DOI: 10.1002/ejoc.200900018

      Thumbnail image of graphical abstract

      Substituted adenosine derivatives have been synthesised by using Sonogashira cross-coupling and click chemistry. The nucleoside analogues show high absorptivities and high fluorescence quantum yields in organic as well as in water solution.

    2. New Approach to the Synthesis of N7-Arylguanines and N7-Aryladenines (pages 1522–1531)

      Roman Keder, Hana Dvořáková and Dalimil Dvořák

      Version of Record online: 19 FEB 2009 | DOI: 10.1002/ejoc.200801002

      Thumbnail image of graphical abstract

      The copper-mediated arylation of 7-methylpyrimido[1,2-a]purin-10(3H)-one (1) in dichloromethane or of N2-(dimethylamino)methyleneguanine (2) in methanolin the presence of TMEDA and subsequent hydrolysis leads to the preferential formation of 7-arylguanines. 7-Aryladenines can similarly be prepared.

    3. Chiral Aminocyclopropanes

      Asymmetric Synthesis of Aminocyclopropanes and N-Cyclopropylamino Alcohols Through Direct Amidocyclopropanation of Alkenes Using Chiral Organozinc Carbenoids (pages 1532–1548)

      Guillaume Bégis, David E. Cladingboel, Laure Jerome, William B. Motherwell and Tom D. Sheppard

      Version of Record online: 23 FEB 2009 | DOI: 10.1002/ejoc.200801033

      Thumbnail image of graphical abstract

      A versatile method is described for the synthesis of a range of enantiopure amino- and amido-cyclopropanes, through the generation of organozinc carbenoids from N-(diethoxymethyl)oxazolidinones.

    4. Fluorecent Chemosensors

      A Selective Metal–Ligand Fluorescent Chemosensor for Dihydrogen Phosphate via Intermolecular Excimer Formation in Water (pages 1549–1553)

      Xiao-huan Huang, Yong-bing He, Chen-guang Hu and Zhi-hong Chen

      Version of Record online: 17 FEB 2009 | DOI: 10.1002/ejoc.200801077

      Thumbnail image of graphical abstract

      The recognition ability of novel receptor 2Zn towards various anions has been studied. The receptor displays an excellent selective fluorescent enhancement of the excimer emissive peak with H2PO4 that is absent with other inorganic anions in water.

    5. Azulene Chemistry

      Electrophilic ipso-Substitution and Some Unique Reaction Behavior of 1,3,6-Tri-tert-butylazulene (pages 1554–1563)

      Taku Shoji, Shunji Ito, Tetsuo Okujima, Junya Higashi, Ryuji Yokoyama, Kozo Toyota, Masafumi Yasunami and Noboru Morita

      Version of Record online: 11 FEB 2009 | DOI: 10.1002/ejoc.200801078

      Thumbnail image of graphical abstract

      Friedel–Crafts and Vilsmeier reactions of 1,3,6-tri-tert-butylazulene (2) gave the corresponding ipso-substitution products 3a, 4a and 5, respectively, in moderate to excellent yields. Treatment of 2 with TPT unexpectedly afforded 1-(trifluoromethyl)thioazulene 10 and 1(8H)-azulenone 11. Compound 2 also reacted with TCNE to give cycloaddition product 13 in excellent yield, rather than the ipso-substitution reaction product.

    6. Fungal Natural Products

      New Naphthalene-Chroman Coupling Products from the Endophytic Fungus, Nodulisporium sp. from Erica arborea (pages 1564–1569)

      Jingqiu Dai, Karsten Krohn, Siegfried Draeger and Barbara Schulz

      Version of Record online: 4 MAR 2009 | DOI: 10.1002/ejoc.200801106

      Thumbnail image of graphical abstract

      The hitherto unknown nodulisporins D–F were isolated from the culture broth ofNodulisporium sp. A naphthalene moiety is coupled to different sites of a chroman or an open-chain analogue. Interestingly, the “monomeric” parts or closely related compounds were also isolated. This example demonstrates the increase of quantity and quality of chemical diversity by coupling of monomeric units.

    7. Designer Dendrimers

      Multi-Tier Dendrimers with an Aromatic Core (pages 1570–1577)

      V. Haridas, Yogesh K. Sharma and Sarala Naik

      Version of Record online: 18 FEB 2009 | DOI: 10.1002/ejoc.200801150

      Thumbnail image of graphical abstract

      Multi-tier designer dendritic molecules that incorporate an aromatic core and heterocyclic and peptide units have been synthesized. The versatility of the synthesis has been illustrated by the synthesis of various symmetrical, unsymmetrical and cationic dendrimers on an aromatic core. The synthesis of such dendrimers will be useful for generating molecules with various functions.

    8. Intramolecular Dipolar Cycloadditions

      Controlling Selectivity for Cycloadditions of Nitrones and Alkenes Tethered by Benzimidazoles: Combining Experiment and Theory (pages 1578–1584)

      Liping Meng, Selina C. Wang, James C. Fettinger, Mark J. Kurth and Dean J. Tantillo

      Version of Record online: 4 MAR 2009 | DOI: 10.1002/ejoc.200801211

      Thumbnail image of graphical abstract

      Theory and experiment were used synergistically to pinpoint the effects of substituents on intramolecular cycloadditions of alkenes with in-situ generated nitrones thatcan produce two different polyheterocyclic scaffolds that position their arrays of functional groups in well-defined but different orientations.

    9. Carbonylative Coupling Reactions

      Carbonylative Suzuki–Miyaura Coupling of Arylboronic Acids with Aryl Iodides Catalyzed by the MCM-41-Supported Bidentate Phosphane Palladium(II) Complex (pages 1585–1591)

      Mingzhong Cai, Guomin Zheng, Lingfang Zha and Jian Peng

      Version of Record online: 18 FEB 2009 | DOI: 10.1002/ejoc.200801253

      Thumbnail image of graphical abstract

      An MCM-41-supported bidentate phosphane palladium(II) complex (MCM-41-2P-PdII) exhibits higher activity and selectivity than [PdCl2(PPh3)2] in the carbonylative Suzuki–Miyaura cross-coupling reactions of arylboronic acids with aryliodides and can be reused at least 10 times without any decrease in activity.

    10. Regioselective Hydrolysis

      Regioselective C-6 Hydrolysis of Methyl O-Benzoyl-pyranosides Catalysed by Candida Rugosa Lipase (pages 1592–1597)

      Aslan Esmurziev, Eirik Sundby and Bård Helge Hoff

      Version of Record online: 18 FEB 2009 | DOI: 10.1002/ejoc.200801268

      Thumbnail image of graphical abstract

      The first examples of enzymatic regioselective hydrolysis of methyl O-benzoyl-pyranosides are reported. Using Candidarugosa lipase as catalyst, the gluco-, galacto-, and mannopyranosides were hydrolysed regioselectively at C-6. The reaction rate was dependant among others on pyranoside structure. The highest yields were obtained for the α-D-galacto-, β-D-galacto- and α-D-glucopyranosides

    11. Enzyme Inhibition

      A Novel Galactosyltransferase Inhibitor with Diamino Sugar as a Pyrophosphate Mimic (pages 1598–1605)

      Nobuyuki Mitsuhashi and Hideya Yuasa

      Version of Record online: 18 FEB 2009 | DOI: 10.1002/ejoc.200801285

      Thumbnail image of graphical abstract

      Conjugates of 2,4-diamino sugars and uridine have been synthesized as galactosyltransferase inhibitors. Their inhibition activities appear to be influenced by theirconformational flexibility and thus their chelation abilities towards MnII within the structure of GalT.

    12. Asymmetric Synthesis

      Synthesis of Enantioenriched Secondary and Tertiary Alcohols via Tricarbonylchromium(0) Complexes of Benzyl Allyl Ethers (pages 1606–1611)

      Keren Abecassis, Susan E. Gibson and Mar Martin-Fontecha

      Version of Record online: 18 FEB 2009 | DOI: 10.1002/ejoc.200900007

      Thumbnail image of graphical abstract

      The tricarbonylchromium(0) complexes of benzyl allyl ethers undergo enantioselective deprotonation/alkylation reactions to giveenantioenriched imidazole alcohols, a triol and a tertiary alcohol after removal of the allyl group.

    13. Organoselenium Chemistry

      Facile Synthesis and Structure of Novel 2,5-Disubstituted 1,3,4-Selenadiazoles (pages 1612–1618)

      Guoxiong Hua, Yang Li, Amy L. Fuller, Alexandra M. Z. Slawin and J. Derek Woollins

      Version of Record online: 11 FEB 2009 | DOI: 10.1002/ejoc.200900013

      Thumbnail image of graphical abstract

      An efficient two-step method for the preparation of a series of novel 2,5-disubstituted 1,3,4-selenadiazoles by selenating with Woollins' reagent (WR) is reported. Sixexamples, representing the first of this class, have been characterised crystallographically.

    14. Intramolecular Conjugate Additions

      New Concise Route to 2-Amino-3-hydroxycycloalkanecarboxylic Acids by Imidate-Mediated Intramolecular Conjugate Addition (pages 1619–1624)

      Yoshitaka Matsushima and Jun Kino

      Version of Record online: 4 MAR 2009 | DOI: 10.1002/ejoc.200801173

      Thumbnail image of graphical abstract

      Trichloroacetimidates undergo stereoselective intramolecular conjugate addition reactions to produce oxazolines. The resulting oxazolines can in a very concise way converted into 2-amino-3-hydroxycycloalkanecarboxylic acids.

    15. Substituted Aryltetrahydropyrans

      Stereoselective Synthesis of 2,6-Disubstituted-4-Aryltetrahydropyrans Using Sakurai–Hosomi–Prins–Friedel–Crafts Reaction (pages 1625–1629)

      Udagandla C. Reddy, Somasekhar Bondalapati and Anil K. Saikia

      Version of Record online: 18 FEB 2009 | DOI: 10.1002/ejoc.200900006

      Thumbnail image of graphical abstract

      The reaction of aldehydes with allyltrimethylsilane afforded 2,6-disubstituted-4-aryltetrahydropyrans through a Sakurai–Hosomi–Prins–Friedel–Craft sequence. The reaction was highly stereoselective.

  9. Correction

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Editorial Survey
    7. Microreview
    8. Short Communications
    9. Full Papers
    10. Correction
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