European Journal of Organic Chemistry

Cover image for Vol. 2014 Issue 27

September 2014

Volume 2014, Issue 27

Pages 5849–6083

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. You have free access to this content
      A Short-Step Synthesis of 1,6-Methano[10]annulene-3,4-dicarboximides and Their Benzene-, Naphthalene-, and Thiophene-Annulated Compounds (Eur. J. Org. Chem. 27/2014)

      Mitsunori Oda, Tomomi Nakamura, Miyako Neha, Daisuke Miyawaki, Akira Ohta, Shigeyasu Kuroda and Ryuta Miyatake

      Article first published online: 16 SEP 2014 | DOI: 10.1002/ejoc.201490075

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      The cover picture shows a rapid stream in a valley of the Hirayu area in the Gifu Prefecture located in the middle of the Japanese mainland. The schemes show an improved one-pot reaction with phosphorane reagents, along the stream, and the previously reported multistep reactions from dicarbaldehydes to 1,6-methano[10]annulene-dicarboximides. The one-pot procedure was successfully applied to the synthesis of the arene-annulated 1,6-methano[10]annulenes. Details are discussed in the article by M. Oda et al. on p. 5976 ff. Even after the eminent achievements by the late Dr. E. Vogel, the field of 1,6-methano[10]annulene chemistry is still interesting and fertile. The authors thank Mr. Yoshimitsu Kumai in our laboratory for his great help in preparing this cover picture.

  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. 27/2014 (pages 5849–5856)

      Article first published online: 16 SEP 2014 | DOI: 10.1002/ejoc.201490077

  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. Palladium Catalysis

      Direct Allylic Functionalization Through Pd-Catalyzed C–H Activation (pages 5863–5883)

      Frédéric Liron, Julie Oble, Mélanie M. Lorion and Giovanni Poli

      Article first published online: 6 MAY 2014 | DOI: 10.1002/ejoc.201402049

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      This review outlines some selected examples and present challenges relating to palladium-catalyzed direct allylic functionalization. This old reaction, ignored for many years, is enjoying a new age.

  5. Short Communications

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

      Tunable Base-Controlled Regioselective Cascade Reaction of 2-Mercaptobenzimidazole with Morita–Baylis–Hillman Acetates of Nitroalkenes (pages 5885–5889)

      Jia-Qiang Zhang, Jie-Jie Liu, Chun-Ling Gu, Dong Wang and Li Liu

      Article first published online: 20 AUG 2014 | DOI: 10.1002/ejoc.201402752

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      Two series of heterocyclic compounds, thiazolo[3,2-a]benzimidazoles and benzimidazo[2,1-b]-1,3-thiazines, are synthesized by the tunable base-controlled regioselective cascade reaction of 2-mercaptobenzimidazole with Morita–Baylis–Hillman acetates of nitroalkenes in good yields with high regioselectivities. DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene.

    2. Alkene Hydrosilylation

      Rhodium-Catalyzed Alkene Hydrosilylation via a Hydride Shuttle Process by Diene Ligands: Dramatic Enhancement of Regio- and Diastereoselectivity (pages 5890–5895)

      Yuanda Hua, Hiep H. Nguyen, Gabriela Trog, Adam S. Berlin and Junha Jeon

      Article first published online: 21 AUG 2014 | DOI: 10.1002/ejoc.201402742

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      A cooperative functional diene ligand and a supporting phosphine ligand mediated, Rh-catalyzed intramolecular alkene hydrosilylation of homoallylic silyl ethers was developed to provide 1,3-trans-oxasilacyclopentanes in a highly regio- and diastereoselective manner. A diene ligand mediated hydride shuttle process is proposed as the mechanistic driving force behind the high level of selectivities.

    3. Iodocyclization

      Copper(I) Iodide Mediated Iodocyclization of Cyclopropylideneallenyl Ketones: Facile and Effective Synthesis of Highly Substituted Furan Derivatives (pages 5896–5900)

      Maozhong Miao, Xin Xu, Lijun Xu and Hongjun Ren

      Article first published online: 15 AUG 2014 | DOI: 10.1002/ejoc.201402823

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      A I2/CuI system promotes the iodocyclization of cyclopropylideneallenyl ketones to produce highly substituted furans under mild conditions. The resulting furans can be transformed into some advanced furan derivatives through nucleophilic substitution and the Pd-catalyzed Suzuki cross-coupling reaction.

    4. Suzuki Coupling

      General Suzuki Coupling of Heteroaryl Bromides by Using Tri-tert-butylphosphine as a Supporting Ligand (pages 5901–5905)

      Yinjun Zou, Guizhou Yue, Jianwei Xu and Jianrong (Steve) Zhou

      Article first published online: 15 AUG 2014 | DOI: 10.1002/ejoc.201402915

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      A fast, general coupling of heteroaryl bromides is realized by using a single palladium catalyst supported by tri-tert-butylphosphine.

    5. Stereoselective Reactions

      Enantioselective Direct Bisvinylogous 1,6-Additions of β-Allyl-2-cyclohexenone to α,α-Dicyanodienes through Trienamine Catalysis (pages 5906–5909)

      Xin Feng, Zhi Zhou, Xiang Yin, Rui Li and Ying-Chun Chen

      Article first published online: 26 AUG 2014 | DOI: 10.1002/ejoc.201402922

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      A highly enantioselective, direct ϵ-regioselective bisvinylogous 1,6-addition reaction of β-allyl-2-cyclohexenone to β-substituted α,α-dicyanodienes is developed through trienamine catalysis of a bifunctional primary amine–thiourea compound. Excellent enantioselectivity is obtained, and more complex cyclic frameworks can be efficiently constructed in a highly stereoselectivity manner. OFBA = o-fluorobenzoic acid.

    6. Synthetic Methods

      Syntheses of 4-Substituted 2-(Trichloromethyl)quinazolines under Mild Conditions by Benzyne [4+2] Cycloaddition (pages 5910–5913)

      Harim Lechuga-Eduardo, Horacio F. Olivo and Moises Romero-Ortega

      Article first published online: 26 AUG 2014 | DOI: 10.1002/ejoc.201402706

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      The preparation of 4-aryl-2-(trichloromethyl)quinazolines under mild conditions by cycloaddition of benzyne with 2-(trichloromethyl)-1,3-diazabutadienes is reported. The 4-aryl-2-(trichloromethyl)-1,3-diazabutadienes are prepared by coupling of trichloroacetamidine with Vilsmeier–Haack reagents. TBAF = tetrabutylammonium fluoride, Tf = trifluoromethylsulfonyl.

  6. Full Papers

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

      A Strategy for Multivalent Presentation of Carba Analogues from N. meningitidis A Capsular Polysaccharide (pages 5915–5924)

      Daniela Ramella, Laura Polito, Stefania Mazzini, Silvia Ronchi, Leonardo Scaglioni, Marcello Marelli and Luigi Lay

      Article first published online: 20 AUG 2014 | DOI: 10.1002/ejoc.201402701

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      Carba analogues of fragments of the N. meningitidis A polysaccharide have been proposed as hydrolytically stable analogues that have immunological activity in mice. Using the MRI technique, we found that when the carba analogues are loaded onto the surface of iron oxide nanoparticles, they show a multivalent effect that enhances their ability to be recognised by MenA antiserum.

    2. Oxidative Coupling

      Ionic-Liquid-Assisted Metal-Free Oxidative Coupling of Amines To Give Imines (pages 5925–5931)

      Antonio Monopoli, Pietro Cotugno, Francesco Iannone, Francesco Ciminale, Maria Michela Dell'Anna, Piero Mastrorilli and Angelo Nacci

      Article first published online: 15 AUG 2014 | DOI: 10.1002/ejoc.201402530

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      An oxidative coupling of amines to give imines in ionic liquids (ILs) under metal-free aerobic conditions has been developed. The efficiency achievable in ILs is explained in terms of activation of the reactants (benzylamine and O2) by an initial electron transfer, promoted by the ionic medium.

    3. Carbonylation

      Stereoselective Synthesis of α-Alkylidene β-Oxo Amides by Palladium-Catalyzed Carbonylation (pages 5932–5938)

      Serena Perrone, Antonio Salomone, Antonio Caroli, Aurelia Falcicchio, Cinzia Citti, Giuseppe Cannazza and Luigino Troisi

      Article first published online: 20 AUG 2014 | DOI: 10.1002/ejoc.201402666

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      A Pd-catalyzed carbonylation of α-chloro ketones in the presence of imines leads to α-alkylidene β-oxo amides in good yields. This one-pot synthetic method is highly stereoselective and affords amides only as (Z) isomers. This work increases the potential of Pd-catalyzed reactions in the direct synthesis of carbonyl compounds.

    4. Atropisomerism and Catalysis

      Tropos Amino Alcohol Mediated Enantioselective Aryl Transfer Reactions to Aromatic Aldehydes (pages 5939–5945)

      Laura Pisani, Carmela Bochicchio, Stefano Superchi and Patrizia Scafato

      Article first published online: 21 AUG 2014 | DOI: 10.1002/ejoc.201402702

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      An application of new amino alcohols that possess a flexible biphenylazepine moiety and can function as tropos catalysts, is presented. In these compounds, the stereogenic center close to the flexible fragment induces a preferred axial chirality and determines the stereochemical outcome of asymmetric reactions. Their efficiency has been explored in the asymmetric arylation of aldehydes.

    5. Organocatalysis

      Properties and Reactivity of Conformationally Constrained Bicyclic Diarylprolinol Silyl Ethers as Organocatalysts (pages 5946–5953)

      Marco Lombardo, Lucia Cerisoli, Elisabetta Manoni, Elisa Montroni, Arianna Quintavalla and Claudio Trombini

      Article first published online: 19 AUG 2014 | DOI: 10.1002/ejoc.201402732

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      Bicyclic silyl ether derivative 1a, which is easily prepared from trans-4-L-hydroxyproline, is much more stable toward protodesilylation than Jørgensen–Hayashi's catalyst 2a. Despite their structural analogy, 1a behaves as a very efficient catalyst in iminium chemistry, but is much less active than 2a in the enamine activation mode. Here, 1a exhibits a higher or equivalent level of stereocontrol.

    6. Peptidic Gelators

      Turning Around the L-Phe-D-Oxd Moiety for a Versatile Low-Molecular-Weight Gelator (pages 5954–5961)

      Lorenzo Milli, Nicola Castellucci and Claudia Tomasini

      Article first published online: 20 AUG 2014 | DOI: 10.1002/ejoc.201402787

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      A small library of 13 peptidomimetics have been prepared and tested as gelators in a plethora of solvents and solvent mixtures. Two molecules were very efficient, Boc-L-Phe-D-Oxd-L-Phe-OBn and Fmoc-L-Phe-D-pGlu-OH, which also efficiently gelated phosphate-buffered saline. A rationale to explain the different behaviour of these peptidomimetics takes into consideration their hydrophobicity.

    7. Kinase Inhibitors

      Phosphatidylinositol 3-Phosphate Mimics Based on a Sulfoquinovose Scaffold: Synthesis and Evaluation as Protein Kinase B Inhibitors (pages 5962–5967)

      Luca Gabrielli, Ilaria Calloni, Giulia Donvito, Barbara Costa, Noemi Arrighetti, Paola Perego, Diego Colombo, Fiamma Ronchetti, Francesco Nicotra and Laura Cipolla

      Article first published online: 27 AUG 2014 | DOI: 10.1002/ejoc.201402664

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      Novel protein kinase B inhibitors have been designed as phosphatidylinositol 3-phosphate mimics and synthesised by using a 6-deoxy-6-sulfoglucose scaffold.

    8. Organochalcogenides

      A Recyclable Biphasic System for Stereoselective and Easily Handled Hydrochalcogenations (pages 5968–5975)

      Caterina Tidei, Luca Sancineto, Luana Bagnoli, Benedetta Battistelli, Francesca Marini and Claudio Santi

      Article first published online: 20 AUG 2014 | DOI: 10.1002/ejoc.201402668

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      Vinyl selenides and vinyl sulfides were prepared by hydrochalcogenation of alkynes with selenols and thiols generated in situ by the reduction of the corresponding diselenides and disulfides with elemental zinc in a biphasic acidic medium. The stereoselectivity and the possibility of reusing the aqueous medium up to ten times are discussed.

    9. Annulation

      A Short-Step Synthesis of 1,6-Methano[10]annulene-3,4-dicarboximides and Their Benzene-, Naphthalene-, and Thiophene-Annulated Compounds (pages 5976–5985)

      Mitsunori Oda, Tomomi Nakamura, Miyako Neha, Daisuke Miyawaki, Akira Ohta, Shigeyasu Kuroda and Ryuta Miyatake

      Article first published online: 28 JUL 2014 | DOI: 10.1002/ejoc.201402776

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      A new one-pot procedure for 1,6-methano[10]annulene-3,4-dicarboximides and its arene-annulated compounds is developed. Cyclohepta-1,3,5-triene-1,6-dicarbaldehyde and its arene-annulated dicarbaldehyde analogs react with various phosphorane reagents to give 1,6-methano[10]annulene-3,4-dicarboximides.

    10. Oxidative C–H Amination

      A Unified Strategy Towards N-Aryl Heterocycles by a One-Pot Copper-Catalyzed Oxidative C–H Amination of Azoles (pages 5986–5997)

      Parthasarathi Subramanian and Krishna P. Kaliappan

      Article first published online: 5 AUG 2014 | DOI: 10.1002/ejoc.201402868

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      An efficient one-pot synthesis of N-aryl heterocycles by a Cu-catalysed double C–N bond formation is reported. This strategy involves a CuI-catalysed C–N bond-forming reaction between azoles and electron-deficient bromopyridines followed by an intramolecular sp2 C–H amination.

    11. Donor–Acceptor Systems

      Donor–Acceptor 1,4-Fluorenylene Chromophores: Photophysics, Electrochemistry, and Synthesis through a Route for Asymmetric Chromophore Preparation (pages 5998–6009)

      Brynna J. Laughlin, Mary K. Burdette, Chadwick R. Powell, Benjamin E. Levy, Andrew G. Tennyson and Rhett C. Smith

      Article first published online: 5 AUG 2014 | DOI: 10.1002/ejoc.201402181

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      A convenient route for the asymmetric derivatization of 1,4-phenylene and 1,4-fluorenylene cores is reported and applied to the preparation of fourteen chromophores. The chromophores were examined by electrochemical techniques, photophysical studies, and DFT calculations.

    12. Flow Chemistry

      An Efficient Partial Reduction of α,β-Unsaturated Esters Using DIBAL-H in Flow (pages 6010–6016)

      Masahito Yoshida, Hiroyuki Otaka and Takayuki Doi

      Article first published online: 6 AUG 2014 | DOI: 10.1002/ejoc.201402675

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      The partial reduction of α,β-unsaturated esters and benzoate derivatives to form the corresponding aldehydes was achieved using a flow reactor system within 1 s at a high flow rate (18 mL min–1) under cryogenic conditions (–97 °C). Commercially available diisobutylaluminium hydride (DIBAL-H) was used as the reductant.

    13. 1,3-Dipolar Cycloaddition

      Stereoselective Synthesis of Enantiopure Cycloalkylglycines by 1,3-Dipolar Cycloaddition of a Chiral Nitrone to Cycloalkenes (pages 6017–6024)

      Heithem Abda, Kaïss Aouadi, Lionel Perrin, Moncef Msaddek, Jean-Pierre Praly and Sébastien Vidal

      Article first published online: 12 AUG 2014 | DOI: 10.1002/ejoc.201402842

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      The 1,3-dipolar cycloaddition of a (–)-menthone-derived nitrone to cycloalkenes afforded isoxazolidines in high yields and with high stereoselectivity. After a one-pot cleavage of the N–O, amide, and N–C–N bonds, the cycloadducts led to α-amino lactones. Subsequent hydrolysis provided enantiopure cycloalkylglycine derivatives in good overall yields (>40 %).

    14. Enhanced Catalytic Activity

      Synergistic Effect of a Bis(proazaphosphatrane) in Mild Palladium-Catalyzed Direct α-Arylations of Nitriles with Aryl Chlorides (pages 6025–6029)

      So Han Kim, Wonseok Jang, Min Kim, John G. Verkade and Youngjo Kim

      Article first published online: 6 AUG 2014 | DOI: 10.1002/ejoc.201402466

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      The effect of a bis(proazaphosphatrane) ligand on the palladium-catalyzed direct α-arylation of nitriles with various aryl chlorides under mild conditions was investigated. Three related mono(proazaphosphatrane) analogues were employed under the same reaction conditions as a comparison to reveal the enhanced catalytic activity of the bis(proazaphosphatrane) ligand.

    15. Enzyme Inhibitors

      Synthesis of Cyclophellitol, Cyclophellitol Aziridine, and Their Tagged Derivatives (pages 6030–6043)

      Kah-Yee Li, Jianbing Jiang, Martin D. Witte, Wouter W. Kallemeijn, Hans van den Elst, Chung-Sing Wong, Sharina D. Chander, Sascha Hoogendoorn, Thomas J. M. Beenakker, Jeroen D. C. Codée, Johannes M. F. G. Aerts, Gijs A. van der Marel and Herman S. Overkleeft

      Article first published online: 14 AUG 2014 | DOI: 10.1002/ejoc.201402588

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      The syntheses of cyclophellitol and of cyclophellitol aziridine from a common intermediate are described. Optimization of the construction of this building block, previously described by Madsen, enables the synthesis of both title compounds. Azide groups are introduced into both cyclitol cores to allow click ligation to a variety of tags, thus yielding a series of retaining glucosidase probes.

    16. Cyclophellitol Derivatives

      Synthesis of α- and β-Galactopyranose-Configured Isomers of Cyclophellitol and Cyclophellitol Aziridine (pages 6044–6056)

      Lianne I. Willems, Thomas J. M. Beenakker, Benjamin Murray, Berend Gagestein, Hans van den Elst, Erwin R. van Rijssel, Jeroen D. C. Codée, Wouter W. Kallemeijn, Johannes M. F. G. Aerts, Gijsbert A. van der Marel and Herman S. Overkleeft

      Article first published online: 14 AUG 2014 | DOI: 10.1002/ejoc.201402589

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      The synthesis of α- and β-galactopyranose-configured derivatives of cyclophellitol and of cyclophellitol aziridine, either non-tagged or functionalized with various reporter entities, is described. All epoxide- and aziridine-based compounds are synthesized from a single cyclohexene precursor – (3S,4S,5S,6R)-3,4-dibenzyloxy-5-hydroxy-6-(hydroxymethyl)cyclohex-1-ene.

    17. Multicomponent Reactions

      Diversity-Oriented Synthesis of Polycyclic Indoles: Brønsted or Lewis Acid Catalyzed Three-Component Reaction for the Synthesis of α-Carbolines and Pyrimidoindoles (pages 6057–6066)

      Rajesh K. Arigela, Ravi Kumar, Srinivas Samala, Sahaj Gupta and Bijoy Kundu

      Article first published online: 5 AUG 2014 | DOI: 10.1002/ejoc.201402633

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      We report the diversity-oriented synthesis of pyrido- and pyrimido-indoles from an acid-catalyzed three-component (3C) reaction involving ethyl 2-amino-1H-indole-3-carboxylates, arylaldehydes, and terminal alkynes. With a Brønsted acid, the 3C reaction furnished a mixture of pyrido- and pyrimido-indoles, whereas when a Lewis acid was used, pyrimidoindoles were obtained as the single product.

    18. Chiral Allenes

      Zinc Salt Promoted Diastereoselective Synthesis of Chiral Propargylamines Using Chiral Piperazines and Their Enantioselective Conversion into Chiral Allenes (pages 6067–6076)

      Mariappan Periasamy, Polimera Obula Reddy, Athukuri Edukondalu, Manasi Dalai, Laxman M. Alakonda and Bantu Udaykumar

      Article first published online: 6 AUG 2014 | DOI: 10.1002/ejoc.201402766

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      A series of chiral piperazine derivatives has been prepared for use in the synthesis of chiral propargylamines for their enantioselective conversion into chiral allenes. The facile cyclodimerization of aryl-substituted allenes suggests ways to overcome the difficulties in handling and storing chiral aryl-substituted allenes.

    19. Cyanophenol Synthesis

      Facile One-Pot Transformation of Phenols into o-Cyanophenols (pages 6077–6083)

      Yuhta Nakai, Katsuhiko Moriyama and Hideo Togo

      Article first published online: 11 AUG 2014 | DOI: 10.1002/ejoc.201402817

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      Various phenols were treated with MgCl2, Et3N, and paraformaldehyde in THF, followed by reaction with molecular iodine and aq. ammonia to provide the corresponding o-cyanophenols in a one-pot manner.

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