European Journal of Organic Chemistry

Cover image for Vol. 2012 Issue 33

November 2012

Volume 2012, Issue 33

Pages 6467–6662

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correction
    1. You have free access to this content
      Configurationally Stable Tris(tetrathioaryl)methyl Molecular Propellers (Eur. J. Org. Chem. 33/2012)

      Benoît Driesschaert, Raphaël Robiette, Cécile S. Le Duff, Laurent Collard, Koen Robeyns, Bernard Gallez and Jacqueline Marchand-Brynaert

      Version of Record online: 12 NOV 2012 | DOI: 10.1002/ejoc.201290090

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      The cover picture shows the left-handed (M) and the right-handed (P) propeller conformations of a stable tris(tetrathioaryl)methyl radical and its isomerization mechanism. Due to steric hindrance, enantiomerization between the two chiral conformations (M and P) of tris(tetrathioaryl)methyl radicals, alcohols and alkanes is restricted allowing isolation of enantiomers. Details of this work are described in the article by J. Marchand-Brynaert et al. on p. 6517 ff.

  2. Graphical Abstract

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

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

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correction
    1. Formal [3+2] Cycloadditions

      Aziridines in Formal [3+2] Cycloadditions: Synthesis of Five-Membered Heterocycles (pages 6479–6501)

      Ana L. Cardoso and Teresa M. V. D. Pinho e Melo

      Version of Record online: 4 JUL 2012 | DOI: 10.1002/ejoc.201200406

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      Aziridines participate in formal [3+2] cycloadditions as masked zwitterionic 1,3-dipoles, generated through C–N bond cleavage, providing routes for the construction of a wide variety of functionalized five-membered heterocycles.

  5. Short Communications

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correction
    1. Photoredox Benzoyloxylation

      Visible-Light-Triggered Direct Benzoyloxylation of Electron-Rich Arenes at Room Temperature without Chelation Assistance (pages 6503–6507)

      Honghua Rao, Ping Wang and Chao-Jun Li

      Version of Record online: 18 OCT 2012 | DOI: 10.1002/ejoc.201201093

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      Visible-light-triggered direct mono-benzoyloxylation of simple electron-rich arenes was demonstrated with a RuII photocatalyst at room temperature. The direct ArC–H benzoyloxylations occurred without chelation assistance. Importantly, various functional groups that displayed diverse reactivities in transition-metal catalyst systems were also tolerated in this photoredox benzoyloxylation process.

    2. Heterogeneous One-Pot Synthesis

      Combined Pd/C and Montmorillonite Catalysis for One-Pot Synthesis of Benzimidazoles (pages 6508–6512)

      Nicholas A. Weires, Jared Boster and Jakob Magolan

      Version of Record online: 22 OCT 2012 | DOI: 10.1002/ejoc.201201101

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      Two heterogeneous catalysts were used concurrently for one-pot sequential redox- and acid-catalyzed processes. This facile procedure yields nineteen benzimidazoles (one pot, three steps) and an antifungal benzimidazoquinazoline (one pot, five steps) directly from ortho-nitroanilines.

    3. C–H Activation

      Catalytic One-Pot Synthesis of 1-Substituted 5,6,7,8-Tetrahydroindolizine Derivatives (pages 6513–6516)

      Tobias Biletzki and Wolfgang Imhof

      Version of Record online: 11 OCT 2012 | DOI: 10.1002/ejoc.201201147

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      Substituted 5,6,7,8-tetrahydroindolizine derivatives are easily accessible by a ruthenium-catalyzed one-pot reaction from α,β-unsaturated aldehydes, but-3-en-1-amine, and carbon monoxide.

  6. Full Papers

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

      Configurationally Stable Tris(tetrathioaryl)methyl Molecular Propellers (pages 6517–6525)

      Benoît Driesschaert, Raphaël Robiette, Cécile S. Le Duff, Laurent Collard, Koen Robeyns, Bernard Gallez and Jacqueline Marchand-Brynaert

      Version of Record online: 9 AUG 2012 | DOI: 10.1002/ejoc.201200801

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      The dynamic stereochemistry of tris(tetrathioaryl)methanols, radicals and tris(tetrathioaryl)methanes is reported. Because of steric hindrance, enantiomerization between right-handed (P) and left-handed (M) propeller conformations is restricted. Using experimental and theoretical approaches, the structure, resolution, conformational stability and mechanism of isomerization have been studied.

    2. Self-Assembly of Porphyrins

      Atropisomeric Chiral Probes to Study the Supramolecular Organization in Porphyrin Self-Assemblies (pages 6526–6536)

      Cyril Chappaz-Gillot, Gabriel Canard, Federico Andreoli, Nicolas Vanthuyne, Michel Giorgi, Jean-Valère Naubron, Valérie Monnier, Roselyne Rosas, Christian Roussel and Teodor Silviu Balaban

      Version of Record online: 9 OCT 2012 | DOI: 10.1002/ejoc.201200985

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      The noncatalysed nucleophilic aromatic substitution was used to introduce various recognition groups on the porphyrin macrocycle of four (bacterio)chlorophyll mimics that self-assemble in nonpolar solutions. An optically pure atropisomer was introduced to produce chiral aggregates. The UV/Vis and ECD spectra of all aggregates can be attributed to a dual H- and J-type supramolecular organization.

    3. Sialic Acids

      Simple and Rapid Procedures for the Synthesis of 5-Acylated 4β-Acylamido- and 4β-Acetoxyneuraminic Acid Glycals (pages 6537–6547)

      Irene S. Agnolin, Paola Rota, Pietro Allevi, Antonio Gregorio and Mario Anastasia

      Version of Record online: 8 OCT 2012 | DOI: 10.1002/ejoc.201201001

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      Simple and rapid procedures affording 4β-acylamido and 4β-acetoxy glycals of Neu5Ac, Neu5Gc and N-perfluorinated congeners, through application of the Ritter reaction or by using an oxazoline intermediate, are described.

    4. Reaction Mechanism

      Mechanistic Understanding of Alkyne Haloboration: An Ab Initio Study (pages 6548–6554)

      Chao Wang and Masanobu Uchiyama

      Version of Record online: 9 OCT 2012 | DOI: 10.1002/ejoc.201200975

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      Ab initio calculations have been performed to understand the mechanisms of alkyne haloborations. The study presents a panorama of reaction pathways, including concerted and stepwise routes. The characteristics of the regio-/stereoselectivity, and the physical chemical uniqueness of this process are investigated.

    5. Cyanide Sensors

      Selective Colorimetric and “Turn-on” Fluorimetric Detection of Cyanide Using a Chemodosimeter Comprising Salicylaldehyde and Triphenylamine Groups (pages 6555–6561)

      Palas Baran Pati and Sanjio S. Zade

      Version of Record online: 11 OCT 2012 | DOI: 10.1002/ejoc.201201085

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      A chemodosimeter having both salicylaldehyde and triphenylamine functionalities, shows selectivity towards cyanide ions. Cyanoalkoxide ions generated after addition of cyanide, exchange with the phenolic proton, leading to strong emission. On addition of cyanide, exchange of the proton develops the charge on the phenolic oxygen, which subsequently leads to intramolecular charge transfer (ICT) to deliver a colorimetric response.

    6. Natural Product Synthesis

      Synthesis of the BCD-Ring Substructure of Granaticin A (pages 6562–6569)

      Janina Bachmann, Christian Mang, Lars Ole Haustedt, Klaus Harms and Ulrich Koert

      Version of Record online: 19 OCT 2012 | DOI: 10.1002/ejoc.201201104

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      A synthesis of the naphthoquinone substructure of granaticin A was achieved by addition of an aryllithium compound to an anhydride followed by a Friedel–Crafts type cyclisation. The stereoselective synthesis of the 2-oxabicyclo[2.2.2]oct-5-ene moiety used a Sharpless asymmetric dihydroxylation and a diastereoselective ketone reduction.

    7. Host-Guest Systems

      Complexation of Paraquat and Diazapyrenium Derivatives with Dipyrido[30]crown-10 (pages 6570–6575)

      Shijun Li, Guan-Huan Weng, Bo Zheng, Xuzhou Yan, Jing Wu, Wei Lin, Huan-Xin Chen and Xi-Chang Zhang

      Version of Record online: 22 OCT 2012 | DOI: 10.1002/ejoc.201200968

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      A new pyridine-containing crown ether, dipyrido[30]crown-10 (DP30C10), has been shown to form [2]pseudorotaxanes spontaneously with paraquat derivatives in solution and in the solid state. The complexation between DP30C10 and N,N′-dimethyl-2,7-diazapyrenium was also investigated. The complexation can be turned on and off by the sequential addition of Et2NH and CF3COOH.

    8. Atorvastatin Linkers

      Synthesis of Atorvastatin Lactone Linker Constructs for Target Fishing (pages 6576–6585)

      Pramod Sawant and Martin E. Maier

      Version of Record online: 15 OCT 2012 | DOI: 10.1002/ejoc.201201154

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      A novel synthesis of the diol-containing side chain of the HMG-CoA reductase inhibitor atorvastatin as well as two aniline-based linkers was developed.

    9. Auto-Tandem Catalysis

      Auto-Tandem Catalysis: Synthesis of Acridines by Pd-Catalyzed C=C Bond Formation and C(sp2)–N Cross-Coupling (pages 6586–6593)

      Zhongxing Huang, Yang Yang, Qing Xiao, Yan Zhang and Jianbo Wang

      Version of Record online: 10 OCT 2012 | DOI: 10.1002/ejoc.201201070

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      A facile and convergent palladium-catalyzed synthesis of acridines using easily accessible o-dihalobenzenes and N-tosylhydrazones has been developed. Two independent steps, namely Pd-catalyzed C=C bond formation and C–N bond formation, have been catalyzed by a single Pd catalyst in a one-pot fashion.

    10. Glycoconjugates on Solid Support

      Synthesis of Biotinylated Multipodal Glycoclusters on a Solid Support (pages 6594–6605)

      Marika Karskela, Miriam von Usedom, Pasi Virta and Harri Lönnberg

      Version of Record online: 8 OCT 2012 | DOI: 10.1002/ejoc.201200926

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      A method for the synthesis of trivalent homo- and heterotypic glycoclusters on a solid support has been developed. On-support oximation was used to conjugate the clusters with an aminooxy-derivatized biotin ligand.

    11. Epoxide Rearrangement

      A Comparison of the Photosensitized Rearrangement and the Lewis-Acid-Catalyzed Rearrangement of Spirooxindole Epoxides (pages 6606–6611)

      Lihong Wang, Yibing Su, Xinmin Xu and Wei Zhang

      Version of Record online: 5 OCT 2012 | DOI: 10.1002/ejoc.201201020

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      Spirooxindole epoxides rearrange either under photosensitization conditions or under Lewis acid catalysis. The photosensitized rearrangement leads to 3-acyl-2-indolones by cleavage of the Cα–O bond followed by alkyl migration. The SnCl4-catalyzed rearrangement gives 4,4-dialkylquinolin-2,3-diones by cleavage of the Cβ–O bond followed by aryl migration.

    12. Cross-Coupling

      Consecutive SNH and Suzuki–Miyaura Cross-Coupling Reactions – an Efficient Synthetic Strategy to Pyrimidines Bearing Pyrrole and Indole Fragments (pages 6612–6621)

      Egor V. Verbitskiy, Gennady L. Rusinov, Valery N. Charushin, Oleg N. Chupakhin, Ekaterina M. Cheprakova, Pavel A. Slepukhin, Marina G. Pervova, Marina A. Ezhikova and Mikhail I. Kodess

      Version of Record online: 8 OCT 2012 | DOI: 10.1002/ejoc.201201035

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      The Suzuki–Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen (SNH) reactions were successfully applied to the syntheses of various 4,5-di(hetero)aryl-substituted pyrimidines. The structures of the intermediate σH adducts as well as the pyrrole-(hetero)arylpyrimidine and indole-(hetero)arylpyrimidine dyads were established by NMR and X-ray crystal structure analysis.

    13. Domino Benzannulation Reaction

      A Microwave-Assisted Domino Benzannulation Reaction towards Functionalized Naphthalenes, Quinolines, and Isoquinolines (pages 6622–6629)

      Yuqin Wang, Cun Tan, Xiaofei Zhang, Qian He, Yuyuan Xie and Chunhao Yang

      Version of Record online: 9 OCT 2012 | DOI: 10.1002/ejoc.201201061

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      Functionalized naphthalenes, quinolines, and isoquinolines were prepared using a versatile palladium/copper-catalyzed domino cross-coupling–isomerization–condensation reaction sequence. This protocol has a broad group tolerance with propargyl alcohols as well as aryl halides.

    14. Carbene Ligands

      Suzuki–Miyaura Cross-Coupling Reaction Catalyzed by PEPPSI-Type 1,4-Di(2,6-diisopropylphenyl)-1,2,3-triazol-5-ylidene (tzIPr) Palladium Complex (pages 6630–6635)

      Jie Huang, Jong-Tai Hong and Soon Hyeok Hong

      Version of Record online: 11 OCT 2012 | DOI: 10.1002/ejoc.201201075

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      The novel 1,4-di(2,6-diisopropylphenyl)-1,2,3-triazol-5-ylidene (tzIPr)-based PEPPSI-type palladium complex showed high activity under mild conditions for the cross-coupling reactions between various types of aryl chlorides and aryl boronic acids regardless of the steric and electronic nature of the substrates.

    15. Butenolides

      A Diels–Alder/Retro-Diels–Alder Approach for the Enantioselective Synthesis of Microbial Butenolides (pages 6636–6646)

      Christian A. Citron, Susanne M. Wickel, Barbara Schulz, Siegfried Draeger and Jeroen S. Dickschat

      Version of Record online: 9 OCT 2012 | DOI: 10.1002/ejoc.201200991

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      The Diels–Alder reaction of cyclopentadiene and citraconic anhydride was followed by reduction to the corresponding lactone and its α-alkylation. Subsequent pyrolysis gave highly substituted butenolides as found in the endophytic fungus Geniculosporium. An enantioselective Diels–Alder reaction was used to stereoselectively synthesise butenolide-signalling molecules from Streptomyces.

    16. Asymmetric Catalysis

      An Asymmetric Organocatalytic Approach to Michael Reactions of Thiazolones and Nitroalkenes: Preparation of Compounds with Anti-Cancer Potency (pages 6647–6655)

      Xiaodong Liu, Hongjin Song, Qiao Chen, Wenyi Li, Wen Yin, Ming Kai and Rui Wang

      Version of Record online: 9 OCT 2012 | DOI: 10.1002/ejoc.201201094

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      The utility of thiazole heterocycles in medicinal chemistry has attracted much attention in the construction of their derivatives. With the aid of a chiral organocatalyst developed from a cinchona alkaloid, a series of chiral thiazolone derivatives were prepared with excellent diastereo- and enantioselectivities. They were found to display strong inhibition of five types of cancer cells in vitro.

    17. Synthetic Phospholipids

      Synthesis and Stability Studies of α,α-Difluoro Ester Phospholipids (pages 6656–6661)

      Palle J. Pedersen, Thomas L. Andresen and Mads H. Clausen

      Version of Record online: 18 OCT 2012 | DOI: 10.1002/ejoc.201200565

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      The stability of synthetic phospholipids 1 and 2 in three different aqueous buffers (pH 4.5, 7.5 and 8.5) was investigated. The studies revealed that the labile α,α-difluoro ester functionality is more prone to hydrolysis when positioned close to the hydrophilic head group than when placed deeper into the lipophilic part of the bilayer in liposomes.

  7. Correction

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correction
    1. You have free access to this content
      Selective Detection of Nerve Agent Simulants by Using Triarylmethanol-Based Chromogenic Chemodosimeters (page 6662)

      Ana M. Costero, Margarita Parra, Salvador Gil, Raúl Gotor, Ramón Martínez-Mañez, Félix Sancenón and Santiago Royo

      Version of Record online: 22 OCT 2012 | DOI: 10.1002/ejoc.201201327

      This article corrects:

      Selective Detection of Nerve Agent Simulants by Using Triarylmethanol-Based Chromogenic Chemodosimeters

      Vol. 2012, Issue 26, 4937–4946, Version of Record online: 25 JUL 2012

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