European Journal of Organic Chemistry

Cover image for Vol. 2009 Issue 11

Special Issue: Dedicated to Professor Alain Krief

April 2009

Volume 2009, Issue 11

Pages 1639–1811

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Microreview
    7. Short Communications
    8. Full Papers
    1. Recent Advances in Organoselenium Chemistry (Eur. J. Org. Chem. 11/2009) (page 1639)

      Diana M. Freudendahl, Sohail A. Shahzad and Thomas Wirth

      Version of Record online: 24 MAR 2009 | DOI: 10.1002/ejoc.200990025

  2. Editorial

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

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

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

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

      Recent Advances in Organoselenium Chemistry (pages 1649–1664)

      Diana M. Freudendahl, Sohail A. Shahzad and Thomas Wirth

      Version of Record online: 4 FEB 2009 | DOI: 10.1002/ejoc.200801171

      Thumbnail image of graphical abstract

      Improved and new selenium-containingreagents and novel reactions are highlighted in this microreview.

  6. Short Communications

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

      Organocatalytic Asymmetric Sulfa-Michael Additions to α,β-Unsaturated Sulfonates (pages 1665–1668)

      Dieter Enders and Krzysztof Hoffman

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/ejoc.200801202

      Thumbnail image of graphical abstract

      A quinine-derived thiourea was found to catalyze the sulfa-Michael addition ofvarious aromatic thiols and α,β-unsaturated sulfonates to afford chiral β-sulfur-substituted sulfonic acid derivatives. Moderate levels of asymmetric induction were achieved in this reaction, which represents the first use of α,β-unsaturated sulfonates in catalytic asymmetric synthesis.

    2. Mechanized Nanoparticles

      Redox- and pH-Controlled Mechanized Nanoparticles (pages 1669–1673)

      Niveen M. Khashab, Ali Trabolsi, Yuen A. Lau, Michael W. Ambrogio, Douglas C. Friedman, Hussam A. Khatib, Jeffrey I. Zink and J. Fraser Stoddart

      Version of Record online: 9 MAR 2009 | DOI: 10.1002/ejoc.200801300

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      Ferrocene-based mechanized nanoparticles have been prepared, loaded with Rhodamine dye, and then capped with either β-cyclodextrin (top) or cucurbit[7]uril (bottom). Both of these systems were operated successfully under redox (oxidation of ferrocenedicarboxylic acid) control in the presence of β-cyclodextrin and under pH (deprotonation of ferrocenedicarboxylic acid at pH > 4) control in the presence of cucurbit[7]uril.

    3. Silacycles

      Towards the Synthesis of 3-Silapiperidines (pages 1674–1678)

      Christophe Blaszykowski, Célia Brancour, Anne-Lise Dhimane, Louis Fensterbank and Max Malacria

      Version of Record online: 5 MAR 2009 | DOI: 10.1002/ejoc.200801197

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      A formal double nucleophilic substitution of dilithiated allylamine on a silylated dielectrophile allows the synthesis of 3-silapiperidines. Further functionalization can give rise to silacycle derivatives.

    4. AlCl3-Promoted Facile E-to-Z Isomerization Route to (Z)-2-Methyl-1-buten-1,4-ylidene Synthons for Highly Efficient and Selective (Z)-Isoprenoid Synthesis (pages 1679–1682)

      Guangwei Wang and Ei-ichi Negishi

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/ejoc.200801188

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      The AlCl3-promoted E-to-Z isomerization of the Zr-catalyzed methylalumination product from 3-butyn-1-ol at 50 °C for 6 h followed by double iodinolysis with I2 in THF and then with I2, PPh3, and imidazolegives 1b (≥98 % Z) in 75 % yield, which can be converted to (Z)-isoprenoids by a Pd-catalyzed alkenylation–homoallylation tandem cross-coupling.

    5. Michael Additions

      Diastereoselective Synthesis of Alkylcyclopropane-Annelated Methyl 2-Iminoimidazolidinecarboxylates (pages 1683–1686)

      Marcus W. Nötzel, Daniel Frank, Thomas Labahn, Jörg Magull and Armin de Meijere

      Version of Record online: 27 FEB 2009 | DOI: 10.1002/ejoc.200801205

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      Mixtures of two diastereometric 2′-alkyl-substituted methyl 2-chloro-2-cyclopropylideneacetates react with N,N′,N″-triarylguanidines to furnish a single diastereomer each of an alkylcyclopropane-annelated2-arylimino-1,3-diaryl-4-carboxylate.

    6. Self Assembly of Metal-Free Carbanions

      Synthesis and Solid-State Structure of Tetrabutylammonium Imidazolate–Dipyrrole Formed by Self Assembly (pages 1687–1690)

      Manfred T. Reetz, H. Martin Herzog and Richard Goddard

      Version of Record online: 26 FEB 2009 | DOI: 10.1002/ejoc.200900020

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      An imidazolate anion, a pyrrole, and an n-tetrabutylammonium cation form a unique supramolecular structure, held together by hydrogen bonds, as shown by X-ray structural analysis.

  7. Full Papers

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

      Dynamic Diels–Alder Reactions of 9,10-Dimethylanthracene: Reversible Adduct Formation, Dynamic Exchange Processes and Thermal Fluorescence Modulation (pages 1691–1697)

      Philippe Reutenauer, Peter J. Boul and Jean-Marie Lehn

      Version of Record online: 4 FEB 2009 | DOI: 10.1002/ejoc.200801269

      Thumbnail image of graphical abstract

      Anthracenes were discovered to be involved in dynamic Diels–Alder reactions at room temperature with three different varieties of cyanoolefins. This permitted thermal control of its fluorescence by displacement of the equilibrium.

    2. Ring Formation

      AuCl3-Catalyzed Hydroalkoxylation of Conjugated Alkynoates: Synthesis of Five- and Six-Membered Cyclic Acetals (pages 1698–1706)

      Alejandro Diéguez-Vázquez, C. Christoph Tzschucke, José Crecente-Campo, Sally McGrath and Steven V. Ley

      Version of Record online: 13 FEB 2009 | DOI: 10.1002/ejoc.200801221

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      The AuIII-catalyzed double hydroalkoxylation of conjugated alkynoates allows rapid access to pyran and furan acetals, which are prevalent structures in numerous polyketide natural products. The mild reaction conditions together with the low toxicity of the catalyst and the high efficiency of the process makes this method promising for extensive applications in organic synthesis.

    3. Plasmepsin Inhibitors

      Synthesis of exo-3-Amino-7-azabicyclo[2.2.1]heptanes as a Class of Malarial Aspartic Protease Inhibitors: Exploration of Two Binding Pockets (pages 1707–1719)

      Martina Zürcher, Fraser Hof, Luzi Barandun, Andri Schütz, W. Bernd Schweizer, Solange Meyer, Daniel Bur and François Diederich

      Version of Record online: 5 MAR 2009 | DOI: 10.1002/ejoc.200801184

      Thumbnail image of graphical abstract

      Substituted exo-3-amino-7-azabicyclo[2.2.1]heptanes as inhibitors of the plasmepsins are described. An O scan of the alkyl-chain substituent, filling the crucial flap pocket at the active site of these malarial aspartic proteases, is reported; dramatic differences in activity were found. Conformational analysis of the ligands is presented, and the basicity of the amine centers is discussed.

    4. Calcitriol Analogues

      Development of Analogues of 1α,25-Dihydroxyvitamin D3 with Biased Side-Chain Orientation: C20 Methylated Des-C,D-homo Analogues (pages 1720–1737)

      Freek Vrielynck, Dirk Van Haver, Maurits Vandewalle, Lieve Verlinden, Annemieke Verstuyf, Roger Bouillon, Gianluca Croce and Pierre De Clercq

      Version of Record online: 13 FEB 2009 | DOI: 10.1002/ejoc.200801183

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      By the stereocontrolled incorporation of two methyl groups at position C20 and at position C13 or C16, the side chain of a series of 6D-analogues of calcitriol is forced into a (g+) orientation, a geometry that is linked to a high antiproliferative activity (MCF-7).

    5. Serine Protease Inhibitors

      Synthesis of Enantiopure α-Chlorocyclobutanones and Cyclobutanols as Scaffolds for the Diverted Synthesis of Serine Protease Inhibitors (pages 1738–1748)

      Gaoqiang Yang and Léon Ghosez

      Version of Record online: 9 MAR 2009 | DOI: 10.1002/ejoc.200900083

      Thumbnail image of graphical abstract

      Resistance to β-lactam antibiotics has become a major threat to public health. We prepared scaffolds equivalent to β-lactams for the diverted total synthesis of hydroxy-alkylating inhibitors of penicillin-binding proteins.

    6. Carbocaclyzation

      Tandem Zn-Brook Rearrangement/Ene-Allene Carbocyclization (pages 1749–1756)

      Rozalia Unger, Theodore Cohen and Ilan Marek

      Version of Record online: 2 MAR 2009 | DOI: 10.1002/ejoc.200900043

      Thumbnail image of graphical abstract

      Metalated alkynes react with acylsilanes in a multi-step reaction to give functionalized carbocycles as single diastereoisomers.

    7. Macrocycle-Embedded Azetidinones

      Novel Large-Ring 1,3-Bridged 2-Azetidinones as Potential Inhibitors of Penicillin-Binding Proteins (pages 1757–1770)

      Allan Urbach, Georges Dive and Jacqueline Marchand-Brynaert

      Version of Record online: 5 FEB 2009 | DOI: 10.1002/ejoc.200801193

      Thumbnail image of graphical abstract

      By using a ring-closing metathesis strategy, non-traditional bicyclic β-lactams featuring high conformational adaptability have been prepared with the aim of developing novel inhibitors of penicillin-binding proteins (serine enzymes).

    8. Galactofuranose Biosynthesis

      Synthesis of Three C-Glycoside Analogues of UDP-Galactopyranose as Conformational Probes for the Mutase-Catalyzed Furanose/Pyranose Interconversion (pages 1771–1780)

      Audrey Caravano and Stéphane P. Vincent

      Version of Record online: 18 FEB 2009 | DOI: 10.1002/ejoc.200801249

      Thumbnail image of graphical abstract

      Three C-glycosidic analogues of UDP-galactopyranose where synthesized and tested as inhibitors of UDP-galactopyranose mutase, an essential enzyme of M. tuberculosis cell wall biosynthesis. Surprisingly, the UDP-exo-galactal displayed competitive inhibition properties although time-dependent inactivation of UGM was expected.

    9. Chemoselective Metallation

      New Mixed Li/Mg and Li/Mg/Zn Amides for the Chemoselective Metallation of Arenes and Heteroarenes (pages 1781–1795)

      Christoph J. Rohbogner, Stefan H. Wunderlich, Giuliano C. Clososki and Paul Knochel

      Version of Record online: 12 MAR 2009 | DOI: 10.1002/ejoc.200801277

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      A wide range of polyfunctional aryl and heteroaryl organometallic reagents have been efficiently prepared in THF by using mixed Mg and Zn bases. The amines used are easy to prepare from cheap bulk chemicals and represent a proper and economic alternative to the well-known and widely investigated amine 2,2,6,6-tetramethylpiperidine. A comparison between the different bases is made.

    10. Human Estrogen Receptor Mimics

      Towards a New SPE Material for EDCs: Fully Automated Synthesis of a Library of Tripodal Receptors Followed by Fast Screening by Affinity LC (pages 1796–1805)

      Steven E. Van der Plas, Els Van Hoeck, Fréderic Lynen, Pat Sandra and Annemieke Madder

      Version of Record online: 9 MAR 2009 | DOI: 10.1002/ejoc.200801290

      Thumbnail image of graphical abstract

      A 120-member parallel library of tripodal human estrogen receptor mimics was prepared. Screening of cleaved library members was performed by affinity LC by using a novel “clicked” estradiol silica HPLC column. Alternatively, alkyne-derivatised library members were reattached on azido-modified silica to construct solid-phase extraction cartridges for extraction of endocrine-disrupting chemicals.

    11. Hydroamination Reactions

      Base-Catalysed Intramolecular Hydroamination of Vinyl Sulfides (pages 1806–1811)

      Coralie Quinet, Laetitia Sampoux and István E. Markó

      Version of Record online: 26 FEB 2009 | DOI: 10.1002/ejoc.200900009

      Thumbnail image of graphical abstract

      Functionalised pyrrolidines and piperidines, as well as bicyclic derivatives akin to the pyrrolizidine, indolizidine and quinolizidine alkaloid families, were smoothly and efficiently generated by a novel, base-catalysed, hydroamination of vinyl sulfides.

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