European Journal of Organic Chemistry

Cover image for Vol. 2010 Issue 1

January 2010

Volume 2010, Issue 1

Pages 3–200

  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. Physicochemical Studies of New Anthocyano-Ellagitannin Hybrid Pigments: About the Origin of the Influence of Oak C-Glycosidic Ellagitannins on Wine Color (Eur. J. Org. Chem. 1/2010) (page 3)

      Stefan Chassaing, Dorothée Lefeuvre, Rémi Jacquet, Michael Jourdes, Laurent Ducasse, Stéphanie Galland, Axelle Grelard, Cédric Saucier, Pierre-Louis Teissedre, Olivier Dangles and Stéphane Quideau

      Version of Record online: 16 DEC 2009 | DOI: 10.1002/ejoc.200990106

  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. Cycloaddition Reactions

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      The Diene Effect: The Design, Development, and Mechanistic Investigation of Metal-Catalyzed Diene-yne, Diene-ene, and Diene-allene [2+2+1] Cycloaddition Reactions (pages 19–32)

      Mitchell P. Croatt and Paul A. Wender

      Version of Record online: 14 OCT 2009 | DOI: 10.1002/ejoc.200900929

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      This review covers the design and development aspects of the recently reported [2+2+1] reactions of dienes tethered to alkynes, alkenes, and allenes. The dienes in these reactions were found to behave very differently than other π-systems and accelerated or enabled the respective [2+2+1] reactions. Additionally, mechanistic insights into these reactions and a synthetic application of the diene-ene [2+2+1] reaction are presented.

  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. Domino Synthesis

      Fluoride-Triggered Domino Reactions Involving Ammonium Acetylides and Carbonyl Compounds (pages 33–37)

      David Tejedor, Sara López-Tosco, Gabriela Méndez-Abt and Fernando García-Tellado

      Version of Record online: 11 NOV 2009 | DOI: 10.1002/ejoc.200901082

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      Fluoride anions were found to trigger domino reactions capable of generating structurally diverse products from methyl propiolate and carbonyl derivatives. These processes construct different molecular architectures through three different autocatalytic reaction networks. Reactions are both bench-friendly and bench-economical: they are performed at room temperature, under an aerobic atmosphere, and by using nondried solvents.

    2. Natural Product Synthesis

      Catalytic Asymmetric Synthesis of Mycolipenic and Mycolipanolic Acid (pages 38–41)

      Bjorn ter Horst, Jeroen van Wermeskerken, Ben L. Feringa and Adriaan J. Minnaard

      Version of Record online: 18 NOV 2009 | DOI: 10.1002/ejoc.200901120

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      The first enantioselective total synthesis of mycolipenic acid and related mycolipanolic acid is described. The acids are prepared by an iterative enantioselective 1,4-addition protocol. The unsaturated system in mycolipenic acid and the propionate moiety in mycolipanolic acid are prepared by stereoselective Wittig olefination and stereoselective Evans aldol reaction, respectively.

    3. Organocatalysis

      Remarkable Reaction Rate and Excellent Enantioselective Direct α-Amination of Aldehydes with Azodicarboxylates Catalyzed by Pyrrolidinylcamphor-Derived Organocatalysts (pages 42–46)

      Pang-Min Liu, Chihliang Chang, Raju Jannapu Reddy, Ying-Fang Ting, Hsuan-Hao Kuan and Kwunmin Chen

      Version of Record online: 5 NOV 2009 | DOI: 10.1002/ejoc.200901151

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      Remarkable reaction rate and excellentenantioselective direct α-amination of aldehydes with various azodicarboxylates was catalyzed by pyrrolidinylcamphor organocatalyst 2a (5 mol-%) to provide the desired aminated products with excellent chemical yield and enantioselectivity (up to >99 % ee) at 0 °C in CH2Cl2.

    4. Friedel–Crafts Alkylations

      Enantioselective Synthesis of Unsymmetrical Triarylmethanes by Chiral Brønsted Acids (pages 47–50)

      Feng-Lai Sun, Xiao-Jian Zheng, Qing Gu, Qing-Li He and Shu-Li You

      Version of Record online: 26 NOV 2009 | DOI: 10.1002/ejoc.200901164

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      Enantioselective synthesis of unsymmetrical triarylmethanes has been realized by a chiral Brønsted acid catalyzed Friedel–Crafts alkylation of electron-rich arenes with (3-indolyl)methanamines. With 5 mol-% of a newly developed chiral phosphoric acid, the enantioenriched unsymmetrical triarylmethanes were obtained in excellent yields with up to 91 % ee.

    5. Fluorinated Heterocycles

      One-Pot Synthesis of Fluorinated 1-Benzoyl-3,4-dihydroisoquinolines from [2-(o-Alkynylphenyl)ethyl]amines by a Hydroamination/Oxidation Sequence (pages 51–54)

      René Severin, Jessica Reimer and Sven Doye

      Version of Record online: 20 NOV 2009 | DOI: 10.1002/ejoc.200901034

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      Potentially antitumor-active fluorinated 1-benzoyl-3,4-dihydroisoquinolines can easily be synthesized by a new one-pot procedure from fluorinated [2-(o-alkynylphenyl)ethyl]amines in high yields. The main reaction steps are an initial Ti-catalyzed intramolecular alkyne hydroamination and a subsequent Pd-catalyzed oxidation.

  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. Grape Pigments

      Physicochemical Studies of New Anthocyano-Ellagitannin Hybrid Pigments: About the Origin of the Influence of Oak C-Glycosidic Ellagitannins on Wine Color (pages 55–63)

      Stefan Chassaing, Dorothée Lefeuvre, Rémi Jacquet, Michael Jourdes, Laurent Ducasse, Stéphanie Galland, Axelle Grelard, Cédric Saucier, Pierre-Louis Teissedre, Olivier Dangles and Stéphane Quideau

      Version of Record online: 30 NOV 2009 | DOI: 10.1002/ejoc.200901133

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      Purple-colored anthocyano-ellagitannins, derived from the oak ellagitannin vescalagin and the red-colored grape pigmentsoenin and malvidin, are likely to play a role in the modulation of wine color during aging in oak barrels.

    2. Carbohydrate Recognition

      Selective Recognition of β-Mannosides by Synthetic Tripodal Receptors: A 3D View of the Recognition Mode by NMR (pages 64–71)

      Ana Ardá, Chiara Venturi, Cristina Nativi, Oscar Francesconi, F. Javier Cañada, Jesús Jiménez-Barbero and Stefano Roelens

      Version of Record online: 20 NOV 2009 | DOI: 10.1002/ejoc.200901024

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      A 3D model of the complex of a synthetic tripodal receptor with octyl β-D-mannoside based on molecular mechanics calculations and NMR experimental data is proposed. The structure explains the observed selectivity for β-mannosyl in terms of hydrogen bonding, intermolecular van der Waals interactions and conformational bias

    3. Blue OLED Material

      Synthesis and Photophysical Properties of Pyrene-Based Light-Emitting Monomers: Highly Pure-Blue-Fluorescent, Cruciform-Shaped Architectures (pages 72–79)

      Jian-yong Hu, Masanao Era, Mark R. J. Elsegood and Takehiko Yamato

      Version of Record online: 11 NOV 2009 | DOI: 10.1002/ejoc.200900806

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      Cruciform-shaped, conjugated monomers based on pyrene were successfully synthesised by a Sonogashira coupling reaction. Both single-crystal X-ray analysis andphotophysical studies strongly indicate their promising use as blue-emitting materials in organic light-emitting diodes (OLEDs).

    4. Synthetic Monophosphoryl Lipid A

      Chemical Synthesis and Proinflammatory Responses of Monophosphoryl Lipid A Adjuvant Candidates (pages 80–91)

      Kaustabh K. Maiti, Michael DeCastro, Abu-Baker M. Abdel-Aal El-Sayed, Matthew I. Foote, Margreet A. Wolfert and Geert-Jan Boons

      Version of Record online: 18 NOV 2009 | DOI: 10.1002/ejoc.200900973

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      A methylated monophosphoryl lipid A derivative exhibits reduced potency and efficacy for cytokine production making it anattractive candidate for adjuvant development.

    5. Dye-Sensitized Solar Cells

      Dye-Sensitized Solar Cells Based on a Novel Fluorescent Dye with a Pyridine Ring and a Pyridinium Dye with the Pyridinium Ring Forming Strong Interactions with Nanocrystalline TiO2 Films (pages 92–100)

      Yousuke Ooyama, Shogo Inoue, Risa Asada, Genta Ito, Kohei Kushimoto, Kenji Komaguchi, Ichiro Imae and Yutaka Harima

      Version of Record online: 24 NOV 2009 | DOI: 10.1002/ejoc.200900983

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      As a new-type donor–acceptor π-conjugated (D–π–A) dye capable of forming a strong interaction between the electron-acceptor moiety of the sensitizer and a TiO2 surface, the fluorescent dye OH11, with a pyridine ring as the electron-accepting group, has been designed and synthesized as a photosensitizer for use in dye-sensitized solar cells (DSSCs).

    6. Electrophilic Reactions

      Highly Selective Synthesis of [(Z)-3-Chloro-2-(phenylselanyl)-1-alkenyl]phosphonates and 2-Ethoxy-4-(phenylselanyl)-2,5-dihydro-1,2-oxaphosphole 2-Oxides by Electrophilic Reaction of 1,2-Alkadienylphosphonates with PhSeCl (pages 101–110)

      Guangke He, Yihua Yu, Chunling Fu and Shengming Ma

      Version of Record online: 5 NOV 2009 | DOI: 10.1002/ejoc.200900913

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      The reactions of monosubstituted 1,2-alkadienylphosphonates with PhSeCl in THF or dioxane/H2O (10:1) afforded [(Z)-3-chloro-2-(phenylselanyl)-1-alkenyl]phosphonates with a very high (Z) stereoselectivity, whereas the same reaction with di- and trisubstituted allenylphosphonates afforded 2-ethoxy-4-(phenylselanyl)-2,5-dihydro-1,2-oxaphosphole 2-oxides exclusively.

    7. Multifunctional Peptide Dendrimers

      A Versatile, Modular Platform for Multivalent Peptide Ligands Based on a Dendritic Wedge (pages 111–119)

      Edith H. M. Lempens, Brett A. Helms, Andrea R. Bayles, Maarten Merkx and E. W. Meijer

      Version of Record online: 27 NOV 2009 | DOI: 10.1002/ejoc.200901045

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      An efficient, modular and broadly applicable strategy is presented for the synthesis of multivalent and multifunctional peptide dendrimers. The scope of the method is demonstrated by introduction of a variety ofpopular targeting peptides at the periphery and other biologically relevant groups at the focal point of ABn-type (n = 2–5) dendrons.

    8. Molecular Electronics

      Synthesis of Rotationally Restricted and Modular Biphenyl Building Blocks (pages 120–133)

      David Vonlanthen, Jürgen Rotzler, Markus Neuburger and Marcel Mayor

      Version of Record online: 4 NOV 2009 | DOI: 10.1002/ejoc.200900805

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      The synthesis of a series of modular biphenyl building blocks with restricted torsion angles is described. Short alkyl bridges dictate the conformation and provide rigid rod-type structures with well-defined backbone conjugation.

    9. Hydrosoluble Triazatruxenes

      Study of a Convenient Method for the Preparation of Hydrosoluble Fluorescent Triazatruxene Derivatives (pages 134–141)

      Marco Franceschin, Luca Ginnari-Satriani, Antonello Alvino, Giancarlo Ortaggi and Armandodoriano Bianco

      Version of Record online: 6 NOV 2009 | DOI: 10.1002/ejoc.200900869

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      In this paper, we compare different synthetic routes for the preparation of hydrophilic triazatruxene derivatives and showthat they are fluorescent both in organic solvents and in water.

    10. Baker's Yeast Stereoselectivity

      Baker's Yeast Reduction of β-Hydroxy Ketones (pages 142–151)

      Daniela Acetti, Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti and Stefano Serra

      Version of Record online: 17 NOV 2009 | DOI: 10.1002/ejoc.200901006

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      Stereoselective reduction of hydroxy ketones by baker's yeast was exploited for concomitant control of the configurations of 1,3-diol triads.

    11. Labelled Tropane Alkaloids

      A Short and Efficient Synthesis of Bridgehead Mono- and Dideuteriated Tropinones (pages 152–156)

      Anaïs Fournial, Tsiresy Ranaivondrambola, Monique Mathé-Allainmat, Richard J. Robins and Jacques Lebreton

      Version of Record online: 26 NOV 2009 | DOI: 10.1002/ejoc.200901018

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      An efficient synthesis of 1,5-dideuterio- and racemic 1-deuteriotropinone is described in which high levels of deuterium are incorporated from the corresponding di- and mono-labelled 2,5-dibutoxytetrahydrofuran, respectively, at either one or both of the bridgehead carbons C-1 and C-5.

    12. Artificial Enzymes

      Amino–Acetone-Bridged Cyclodextrins ― Artificial Alcohol Oxidases (pages 157–167)

      Lavinia G. Marinescu, Elisa G. Doyagüez, Marta Petrillo, Alfonso Fernández-Mayoralas and Mikael Bols

      Version of Record online: 24 NOV 2009 | DOI: 10.1002/ejoc.200901099

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      Three amino–acetone-bridged cyclodextrins have been synthesized and kinetic studies revealed very good substrate-selective enzymatic catalysis for the oxidation of benzyl alcohols with a rate increase of up to 18500 under neutral conditions at room temperature using hydrogen peroxide as co-oxidant. They also exhibit stereoselectivity in the oxidation of different enantiomers.

    13. Green Chemistry

      Green Synthesis of Vicinal Dithioethers and Alkenyl Thioethers from the Reaction of Alkynes and Thiols in Water (pages 168–173)

      Zhuang Jin, Bo Xu and Gerald B. Hammond

      Version of Record online: 17 NOV 2009 | DOI: 10.1002/ejoc.200901101

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      Alkynes reacted with thiols in water to give vicinal dithioethers, and non-terminal propargyl alcohols reacted with phenyl thiols to produce a highly regio and stereoselective monohydrothiolation product, (E)-alkenyl thioether.

    14. Asymmetric Catalysis

      Enantioselective Fujiwara–Moritani Indole and Pyrrole Annulations Catalyzed by Chiral Palladium(II)–NicOx Complexes (pages 174–182)

      Julia A. Schiffner, Thorsten H. Wöste and Martin Oestreich

      Version of Record online: 20 NOV 2009 | DOI: 10.1002/ejoc.200901129

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      The long known Fujiwara–Moritani arylation of alkenes, an oxidative palladium(II) catalysis, is finally accomplished in an asymmetric sense. C–H bond activation at indoles and pyrroles followed by conventional Heck-type C–C bond formation allows for enantioselective construction of a congested quaternary carbon atom.

    15. Asymmetric Tandem Process

      An Asymmetric Tandem Conjugative Addition-Intramolecular Cyclisation Process to Provide Functionalised 3,6-Dihydropyrans and 4,5-Epoxytetrahydropyrans (pages 183–190)

      Silvia Catalán-Muñoz, Constanze A. Müller and Steven V. Ley

      Version of Record online: 20 NOV 2009 | DOI: 10.1002/ejoc.200901145

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      An efficient and convenient two-step synthesis of enantiomerically enriched dihydropyran and epoxytetrahydropyran derivatives is described. The key step involvesa tandem conjugative addition-intramolecular cyclisation/epoxidation process from easily available enantiomerically pure β-hydroxy aldehydes.

    16. Multisubstituted Pyrroles

      A New Method for the Synthesis of Multisubstituted Pyrroles of Biological Interest by Double Nucleophilic Addition to α,β-Unsaturated Imines (pages 191–200)

      Atsushi Takahashi, Shiho Kawai, Iwao Hachiya and Makoto Shimizu

      Version of Record online: 27 NOV 2009 | DOI: 10.1002/ejoc.200901055

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      The double nucleophilic addition reactions of dialkoxy ketene silyl acetals proceeded with α,β-unsaturated imines to give 1,4-and 1,2-double addition products, and their subsequent transformations afforded multisubstituted pyrroles in good yields.

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