European Journal of Organic Chemistry

Cover image for Vol. 2009 Issue 15

May 2009

Volume 2009, Issue 15

Pages 2375–2580

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communication
    7. Full Papers
    1. Click Multivalent Homogeneous Neoglycoconjugates – Synthesis and Evaluation of Their Binding Affinities (Eur. J. Org. Chem. 15/2009) (page 2375)

      Francisco Perez-Balderas, Julia Morales-Sanfrutos, Fernando Hernandez-Mateo, Joaquín Isac-García and Francisco Santoyo-Gonzalez

      Article first published online: 5 MAY 2009 | DOI: 10.1002/ejoc.200990038

  2. Graphical Abstract

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

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

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communication
    7. Full Papers
    1. Binolams

      Bifunctional Binols: Chiral 3,3′-Bis(aminomethyl)-1,1′-bi-2-naphthols (Binolams) in Asymmetric Catalysis (pages 2385–2400)

      Carmen Nájera, José M. Sansano and José M. Saá

      Article first published online: 2 FEB 2009 | DOI: 10.1002/ejoc.200801069

      Thumbnail image of graphical abstract

      3,3′-Bis(dialkylaminomethyl)-1,1′-binaphth-2-ols act both as organocatalysts and as chiral ligands for many metal-catalyzed processes. Their most valuable feature is their capacity to activate both nucleophiles and electrophiles. Transformations carried out with these bifunctional catalysts include cyanation of aldehydes and ketones and enantioselective nucleophilic addition to C=O or C=N bonds.

    2. Aza-Henry Reactions

      Catalytic Enantioselective Aza-Henry Reactions (pages 2401–2420)

      Eugenia Marqués-López, Pedro Merino, Tomás Tejero and Raquel P. Herrera

      Article first published online: 5 FEB 2009 | DOI: 10.1002/ejoc.200801097

      Thumbnail image of graphical abstract

      In recent years, catalytic asymmetric aza-Henry reactions have been increasingly reported, and excellent results in terms of diastereo- and enantioselectivity have been achieved. A variety of metal-based and organic catalysts have been developed, allowing the scope of substrates used to be widened. This review covers recent achievements relating to the catalytic asymmetric aza-Henry reaction.

    3. Strategies for the Synthesis of Stemona Alkaloids (pages 2421–2435)

      Ramon Alibés and Marta Figueredo

      Article first published online: 31 MAR 2009 | DOI: 10.1002/ejoc.200900037

      Thumbnail image of graphical abstract

      This microreview examines successful synthetic approaches to Stemona alkaloids belonging to the stemoamide, tuberostemospironine, and stenine groups, according to the strategies devised to assemble their intricate structures.

  5. Short Communication

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communication
    7. Full Papers
    1. Indium Catalysis

      Synthesis of Methanes Having Four Different Carbon Substituents Utilizing Indium-Catalyzed Cleavage of Carbon–Pyrrolyl Bonds (pages 2437–2440)

      Teruhisa Tsuchimoto, Taku Ainoya, Kazuki Aoki, Tatsuya Wagatsuma and Eiji Shirakawa

      Article first published online: 14 APR 2009 | DOI: 10.1002/ejoc.200900246

      Thumbnail image of graphical abstract

      Methanes having four different carbon substituents, one of which is a β-pyrrolyl group, have been successfully prepared by the reaction of β,β′-dipyrrolylalkanes with carbon nucleophiles in the presence of anindium catalyst. The reaction can be performed also as a three-component assembly of alkynes, pyrroles, and carbon nucleophiles in an easy manner.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communication
    7. Full Papers
    1. Click Chemistry

      Click Multivalent Homogeneous Neoglycoconjugates – Synthesis and Evaluation of Their Binding Affinities (pages 2441–2453)

      Francisco Perez-Balderas, Julia Morales-Sanfrutos, Fernando Hernandez-Mateo, Joaquín Isac-García and Francisco Santoyo-Gonzalez

      Article first published online: 2 APR 2009 | DOI: 10.1002/ejoc.200801170

      Thumbnail image of graphical abstract

      Structurally diverse multivalent neoglycoconjugates containing mannose (α-Man) residues were synthesized by two different click-chemistry based strategies and their binding affinities toward Con A were evaluated.

    2. Click Multivalent Heterogeneous Neoglycoconjugates – Modular Synthesis and Evaluation of Their Binding Affinities (pages 2454–2473)

      Mariano Ortega-Muñoz, Francisco Perez-Balderas, Julia Morales-Sanfrutos, Fernando Hernandez-Mateo, Joaquín Isac-García and Francisco Santoyo-Gonzalez

      Article first published online: 2 APR 2009 | DOI: 10.1002/ejoc.200801169

      Thumbnail image of graphical abstract

      Multivalent neoglycoconjugates containing two different sugars were synthesized by a modular strategy based in the CuI-catalyzed azide-alkyne cycloaddition reaction and their binding affinities toward Concanavalin A were evaluated.

    3. Sphingolipid Mimics

      Highly Regioselective Oxirane Ring-Opening of a Versatile Epoxypyrrolidine Precursor of New Imino-Sugar-Based Sphingolipid Mimics (pages 2474–2489)

      Arnaud Rives, Yves Génisson, Vanessa Faugeroux, Chantal Zedde, Christine Lepetit, Remi Chauvin, Nathalie Saffon, Nathalie Andrieu-Abadie, Sandra Colié, Thierry Levade and Michel Baltas

      Article first published online: 8 APR 2009 | DOI: 10.1002/ejoc.200900100

      Thumbnail image of graphical abstract

      The generalization to various nucleophiles of the regioselective oxirane ring-opening reaction of a key epoxypyrrolidine has paved the way for the preparation of five-membered-ring imino-sugar-based sphingolipid mimics that display strong cytotoxicity and interfere with the sphingolipid metabolism in murine melanoma cells.

    4. Polycyclic Quinazolinones

      Preparation of Fused Tetracyclic Quinazolinones by Combinations of Aza-Wittig Methodologies and CuI-Catalysed Heteroarylation Processes (pages 2490–2504)

      Juan Antonio Bleda, Pilar M. Fresneda, Raul Orenes and Pedro Molina

      Article first published online: 8 APR 2009 | DOI: 10.1002/ejoc.200900082

      Thumbnail image of graphical abstract

      Aza-Wittig reactions of iminophosphoranes obtained from N-aryl-substituted o-azidobenzamides with isocyanates or CS2 and subsequent CuI-catalysed heteroarylation provided fused quinazolinones.

    5. Cascade Processes

      A Single-Step Synthesis of 4-Oxazolin-2-ones and Their Use in the Construction of Polycyclic Structures Bearing Quaternary Stereocenters (pages 2505–2518)

      Blanca M. Santoyo, Carlos González-Romero, Omar Merino, Rafael Martínez-Palou, Aydeé Fuentes-Benites, Hugo A. Jiménez-Vázquez, Francisco Delgado and Joaquín Tamariz

      Article first published online: 14 APR 2009 | DOI: 10.1002/ejoc.200900114

      Thumbnail image of graphical abstract

      Two methods for the one-step synthesis of N-substituted 4-oxazolin-2-ones in highyields under thermal and MW irradiation conditions are described. These molecules are reactive and regioselective nucleophiles with Michael acceptors and prenyl bromide, providing a variety of bicyclic molecules with quaternary stereocenters.

    6. CT Host System

      Colored Supramolecular Host System Using a Charge-Transfer Complex Composed of 1,1′-Bi-2-naphthol and 2,5-Substituted 1,4-Benzoquinone (pages 2519–2525)

      Yoshitane Imai, Kensaku Kamon, Takafumi Kinuta, Tomohiro Sato, Nobuo Tajima, Reiko Kuroda and Yoshio Matsubara

      Article first published online: 8 APR 2009 | DOI: 10.1002/ejoc.200900004

      Thumbnail image of graphical abstract

      A colored charge-transfer (CT) host system composed of rac-1,1′-bi-2-naphthol and 2,5-substituted 1,4-benzoquinone was developed. This CT host system can selectively include aromatic molecules as guests by tuning the packing of donor and acceptor molecules. Characteristically, the color and diffuse reflectance spectra (DRS) of this inclusion CT complex can be tuned by changing the type of the component 2,5-substituted 1,4-benzoquinone.

    7. Enzymatic Catalysis

      Enzymatic Baeyer–Villiger Oxidation of Benzo-Fused Ketones: Formation of Regiocomplementary Lactones (pages 2526–2532)

      Ana Rioz-Martínez, Gonzalo de Gonzalo, Daniel E. Torres Pazmiño, Marco W. Fraaije and Vicente Gotor

      Article first published online: 9 APR 2009 | DOI: 10.1002/ejoc.200900084

      Thumbnail image of graphical abstract

      Three Baeyer–Villiger monoxygenases have been tested in the oxidation of a set of benzo-fused ketones in order to obtain the corresponding lactones. By employing non-conventional reaction media, organic solvent/aqueous buffer, higher activities can be achieved. Different regioselectivities were observed depending on the biocatalyst used.

    8. Synthesis of Enantiopure Amines

      Stereoselective Chemoenzymatic Synthesis of Enantiopure 1-(Heteroaryl)ethanamines by Lipase-Catalysed Kinetic Resolutions (pages 2533–2538)

      Sergio Alatorre-Santamaría, Vicente Gotor-Fernández and Vicente Gotor

      Article first published online: 8 APR 2009 | DOI: 10.1002/ejoc.200900150

      Thumbnail image of graphical abstract

      The chemical preparation and enzymatic kinetic resolution of a family of racemic 1-(heteroaryl)ethanamines is presented. Excellent reaction rates and enantioselectivities have been achieved, especially whenusing Candida antarctica lipase type B as the biocatalyst.

    9. Asymmetric Catalysis

      Combinations of Acidic and Basic Monodentate Binaphtholic Phosphites as Supramolecular Bidentate Ligands for Enantioselective Rh-Catalyzed Hydrogenations (pages 2539–2547)

      Luca Pignataro, Benita Lynikaite, Ján Cvengroš, Mattia Marchini, Umberto Piarulli and Cesare Gennari

      Article first published online: 8 APR 2009 | DOI: 10.1002/ejoc.200900158

      Thumbnail image of graphical abstract

      The combination of two chiral BINOL-derived monodentate phosphites, containing either a carboxylic acid or a tertiary amine, can be seen as a supramolecular bidentate P-ligand self-assembled through an acid–base interaction. These ligands are effective in the Rh-catalyzed enantioselective hydrogenation of methyl 2-acetamidoacrylate.

    10. Nitronyl and Imino Nitroxides

      New Cascade Syntheses of Nitronyl Nitroxides and a New Synthetic Approach to Imino Nitroxides (pages 2548–2561)

      Eugene Tretyakov, Svyatoslav Tolstikov, Aleksander Mareev, Alevtina Medvedeva, Galina Romanenko, Dmitry Stass, Artem Bogomyakov and Victor Ovcharenko

      Article first published online: 8 APR 2009 | DOI: 10.1002/ejoc.200801237

      Thumbnail image of graphical abstract

      Cascade reactions between 1a and MnO2 have been found: one-pot treatment of 1a in MnO2/MeOH, for example, results in formation of the nitronyl nitroxide (NN), Me3Si elimination, and regiospecific MeOH addition to give (Z)- and (E)-NN–HC=CH–OMe. In MeNO2, 2-substituted 4,4,5,5-tetramethylimidazolidine-1,3-diolsgave imino nitroxides (INs), including IN–C≡C–SiMe3, which was converted into IN–C≡CH.

    11. Shape-Switchable Azo-Macrocycles

      Shape-Switchable Azo-Macrocycles (pages 2562–2575)

      Marcel Müri, Klaus C. Schuermann, Luisa De Cola and Marcel Mayor

      Article first published online: 9 APR 2009 | DOI: 10.1002/ejoc.200801282

      Thumbnail image of graphical abstract

      The synthesis of four differently substituted azo-macrocycles is reported. Their optically and/or thermally triggered isomerization reactions were investigated by UV/Vis spectroscopy and displayed very slow thermal back-reactions due to the mechanical interlinking of the two azo groups within each compound.

    12. Aza-Diels–Alder Reactions

      Brønsted Acid or Solid Acid Catalyzed Aza-Diels–Alder Reactions of Methylenecyclopropanes with Ethyl (Arylimino)acetates (pages 2576–2580)

      Zhi-Bin Zhu, Li-Xiong Shao and Min Shi

      Article first published online: 8 APR 2009 | DOI: 10.1002/ejoc.200900050

      Thumbnail image of graphical abstract

      Tetrahydroquinolines were obtained through the Brønsted acid or solid acid catalyzed aza-Diels–Alder reactions of methylenecyclopropanes with ethyl (arylimino)acetates.

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