European Journal of Organic Chemistry

Cover image for Vol. 2018 Issue 3

Early View (Online Version of Record published before inclusion in an issue)

Managing Editor: Anne Nijs

Impact Factor: 2.834

ISI Journal Citation Reports © Ranking: 2016: 19/59 (Chemistry Organic)

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry

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  1. 1 - 27
  1. Full Papers

    1. Library Synthesis in Flow

      Continuous Flow Synthesis of Urea-Containing Compound Libraries Based on the Piperidin-4-one Scaffold

      Alejandra Riesco-Domínguez, Daniel Blanco-Ania and Floris P. J. T. Rutjes

      Version of Record online: 22 JAN 2018 | DOI: 10.1002/ejoc.201701539

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      Two libraries of urea compounds based on the piperidin-4-one scaffold have been developed in continuous flow and twenty drug-like compounds were synthesized in moderate to high yields.

  2. Microreviews

    1. Hydrozirconation

      Hydrozirconation of C=X Functionalities with Schwartz's Reagent

      Michał M. Więcław and Sebastian Stecko

      Version of Record online: 19 JAN 2018 | DOI: 10.1002/ejoc.201701537

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      This Microreview covers the reactions of [Cp2Zr(H)Cl] with C=X functionalities, such as amides, lactams, nitriles or isocyanates, as a method for chemoselective preparation of functionalized organic molecules, for instance aldehydes, amines, and amides.

  3. Communications

    1. Brook Rearrangement

      Enantiospecific Brook Rearrangement of Tertiary Benzylic α-Hydroxysilanes

      Juan F. Collados, Pablo Ortiz, Juana M. Pérez, Yiyin Xia, Mark A. J. Koenis, Wybren J. Buma, Valentin P. Nicu and Syuzanna R. Harutyunyan

      Version of Record online: 19 JAN 2018 | DOI: 10.1002/ejoc.201701469

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      Chiral tertiary benzylic α-hydroxysilanes, upon treatment with LiOtBu, undergo Brook rearrangement, which is enantiospecific and proceeds with inversion of the configuration.

    2. Strained Heterocycles

      Synthesis and Unusual NMR-Spectroscopic Behavior of a Strained Bicyclic Ammonium Salt

      Stefan Pusch, Dieter Schollmeyer and Till Opatz

      Version of Record online: 17 JAN 2018 | DOI: 10.1002/ejoc.201701594

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      The first example of an 2-azabicyclo[2.2.0]hexenium system is described. This strained bicyclic ammonium cation was characterized by NMR spectroscopy and XRD. The unusual coupling behavior and the strong πC=C[RIGHTWARDS ARROW]σ*C–N hyperconjugation were studied by DFT calculations.

    3. Catalytic Fluorination/Aldolization

      Organo- and Copper-Multi-Catalyzed Pseudo Four-Component Access to gem-Difluorohydrins

      Angela Ricucci, Jean Rodriguez and Adrien Quintard

      Version of Record online: 17 JAN 2018 | DOI: 10.1002/ejoc.201701459

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      A combination of organocatalytic aldehyde gem-difluorination and copper-catalyzed decarboxylative aldolization has been developed providing a one-pot access to gem-difluorohydrins. This is possible by the in situ generation and trapping of the volatile bis-fluorinated aldehyde intermediates using a compatible decarboxylative aldolization, resulting in the otherwise difficult C–C bond formation.

    4. C–S Coupling

      Nickel-Catalyzed Synthesis of Diaryl Sulfones from Aryl Halides and Sodium Sulfinates

      Nai-Wei Liu, Shuai Liang, Natalie Margraf, Saad Shaaban, Vanessa Luciano, Marcella Drost and Georg Manolikakes

      Version of Record online: 17 JAN 2018 | DOI: 10.1002/ejoc.201701478

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      A nickel-catalyzed cross-coupling of sodium sulfinates with aryl halides is reported. The reaction provides diaryl sulfones in good yields and displays a broad tolerance towards functional groups.

  4. Cover Picture

    1. You have free access to this content
      Front Cover: Synthesis and Applicability of Base-Discriminating DNA-Triplex-Forming 19F NMR Probes (Eur. J. Org. Chem. /2018)

      Naresh Bhuma, Ville Tähtinen and Pasi Virta

      Version of Record online: 16 JAN 2018 | DOI: 10.1002/ejoc.201800052

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      The Front Cover shows triplex-forming 19F NMR probes that recognize nucleobase content in the pyrimidine-rich strand of double-helical DNA targets. The obtained 19F NMR resonances are sensitive to the base content, and unique 19F NMR-spectral fingerprints could be obtained. The idea of the probes may find application in studies in which the goal is to simultaneously detect changes of local environments (e.g., upon binding of nucleobase-specific ligands) in structurally resembling double-helical stretches. More information can be found in the Full Paper by N. Bhuma, V. Tähtinen, and P. Virta.

  5. Microreviews

    1. Carbon Dioxide Fixation

      Recent Advances in Palladium-Catalyzed Carboxylation with CO2

      Jian Song, Qing Liu, Hui Liu and Xuefeng Jiang

      Version of Record online: 11 JAN 2018 | DOI: 10.1002/ejoc.201701436

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      An overview of recent advances in palladium-catalyzed carboxylation with carbon dioxide as a C1 carbon source is presented: carboxylation of organic halides with CO2, carboxylation with nucleophiles, catalytic carboxylation via π-allylic intermediates, and some other special examples are covered.

    2. Functional Fluorescent Dyes

      Diaminoterephthalate Fluorescence Dyes – Versatile Tools for Life Sciences and Materials Science

      Jens Christoffers

      Version of Record online: 11 JAN 2018 | DOI: 10.1002/ejoc.201701447

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      The diaminoterephthalate chromophore defines a fluorescent scaffold being facilely equipped with different functional units (FU) starting from orthogonally protected succinyl succinates.

  6. Author Profile

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      Hans-Günther Schmalz

      Version of Record online: 11 JAN 2018 | DOI: 10.1002/ejoc.201800009

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      “Unforgettable moments are when you learn that a tediously synthesized molecule exhibits the desired (or even superior) biological activity …” Find out more about this author's research at https://doi.org/10.1002/ejoc.201701584.

  7. Front Cover

    1. You have free access to this content
      Front Cover: Directed ortho-Metalation of O-Aryl N,N-Dialkylcarbamates: Methodology, Anionic ortho-Fries Rearrangement, and Lateral Metalation (Eur. J. Org. Chem. /2018)

      M. A. Jalil Miah, Mukund P. Sibi, S. Chattopadhyay, Oluwole B. Familoni and Victor Snieckus

      Version of Record online: 10 JAN 2018 | DOI: 10.1002/ejoc.201800016

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      The Front Cover shows a wheel centered on the aryl ortho-lithiated O-carbamate represented by the maple leaf (imagine a benzene ring) and by two ethyl hockey-stick groups (both symbolic to Canada), the carbamate's partial history, its anionic equivalency to the venerable Fries rearrangement, and its rich chemistry. Follow the wheel from 12 o'clock in an R configuration passing through a carbamate used for treatment of a neuromuscular disease, through Karl Fries, and ending in directed ortho-metalation (DoM), anionic ortho-Fries rearrangement (AoF), and walking-around-the-ring DoM – all very useful reactions for synthetic aromatic chemistry. More information can be found in the Full Papers (ejoc.201701142 and ejoc.201701143) by M. A. J. Miah, V. Snieckus et al.

  8. Author Profile

    1. You have free access to this content
      Pablo Ballester

      Version of Record online: 9 JAN 2018 | DOI: 10.1002/ejoc.201701742

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      “We are thus able to apply our synthetic receptors, which typically work in solution, in real-world sensing devices …” Find out more about this author's research at https://doi.org/10.1002/ejoc.201701602.

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      Ilan Marek

      Version of Record online: 4 JAN 2018 | DOI: 10.1002/ejoc.201701767

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      “I was attracted by the beauty of chemical transformations …” Find out more about this author's research at https://doi.org/10.1002/ejoc.201701516.

  9. Full Papers

    1. Photoactive Receptors | Very Important Paper

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      Synthesis and Binding Studies of a Tetra-α Aryl-Extended Photoresponsive Calix[4]pyrrole Receptor Bearing meso-Alkyl Substituents

      Luis Escobar, Frank A. Arroyave and Pablo Ballester

      Version of Record online: 3 JAN 2018 | DOI: 10.1002/ejoc.201701602

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      Synthesis of the tetra-α isomer of a meso-azobenzene-extended calix[4]pyrrole and photo-irradiation of the all-trans receptor induces the isomerization of its azobenzene units, producing a mixture enriched with the cis-counterpart. Its interaction with electron-rich molecular guests (neutral and anionic) was probed using 1H NMR spectroscopic titrations and isothermal titration calorimetry (ITC).

  10. Microreviews

    1. Cycloadditions

      Transition-Metal-Catalyzed [3+2+2] Cycloaddition Reactions

      Bilash Kuila, Maninderjeet Kaur, Prabhpreet Singh and Gaurav Bhargava

      Version of Record online: 21 DEC 2017 | DOI: 10.1002/ejoc.201701116

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      [3+2+2] Cycloaddition reactions are important for the synthesis of seven-membered carbocycles. [3+2+2] Cycloadditions of different substrates afford cycloheptane derivatives, 6–7, 5–7 condensed bicyclic carbocycles, or 5–7–5 and 6–7–5 condensed tricyclic carbocycles. Higher-order cycloaddition reactions may provide an easy route for the total synthesis of natural products, or as a key synthetic step towards the final structure. This review summarizes the different reports on [3+2+2] cycloaddition reactions since 2000.

    2. Heterocycle Synthesis

      Recent Advances in Iodosobenzene-Mediated Construction of Heterocyclic Scaffolds: Transition-Metal-Free Approaches and Scope

      Krishnanka Shekhar Gayen, Nirbhik Chatterjee, Saikat Khamarui and Pradip Kumar Tarafdar

      Version of Record online: 20 DEC 2017 | DOI: 10.1002/ejoc.201701306

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      Transition-metal-free iodosobenzene-mediated convenient and environmentally friendly protocols were delineated adequately to illustrate the practical findings and mechanistic points of view for the synthesis of heterocyclic motifs.

    3. Asymmetric Synthesis

      Levoglucosenone and Its New Applications: Valorization of Cellulose Residues

      María B. Comba, Yi-hsuan Tsai, Ariel M. Sarotti, María I. Mangione, Alejandra G. Suárez and Rolando A. Spanevello

      Version of Record online: 19 DEC 2017 | DOI: 10.1002/ejoc.201701227

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      Levoglucosenone is a versatile chiral building block that is obtained from the pyrolytic recycling of cellulosic biomass residues. This compound has been innovatively used as a template for the synthesis of key intermediates of biologically active products and for the preparation of chiral auxiliaries, catalysts, and organocatalysts for their applications in asymmetric synthesis.

  11. Full Papers

    1. Secondary-Structure Mimetics

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      Design and Synthesis of Building Blocks for PPII-Helix Secondary-Structure Mimetics: A Stereoselective Entry to 4-Substituted 5-Vinylprolines

      Slim Chiha, Arne Soicke, Matthias Barone, Matthias Müller, Judith Bruns, Robert Opitz, Jörg-Martin Neudörfl, Ronald Kühne and Hans-Günther Schmalz

      Version of Record online: 19 DEC 2017 | DOI: 10.1002/ejoc.201701584

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      Starting from pyroglutamic acid, 4-substituted-5-vinylprolines were stereoselectively prepared and used as building blocks for the synthesis of conformationally well-defined diproline analogs, which are of interest as proline-derived modules (ProMs) for the construction of PPII-helix secondary-structure mimetics acting as inhibitors of relevant protein-protein interactions.

  12. Communications

    1. Molecular Knots

      Attempted [2]Catenane Synthesis via a Quasi[1]catenane by a Templated Backfolding Strategy

      Luuk Steemers, Martin J. Wanner, Bart R. C. van Leeuwen, Henk Hiemstra and Jan H. van Maarseveen

      Version of Record online: 8 DEC 2017 | DOI: 10.1002/ejoc.201701325

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      A tartaric acid derived ketal-centered quasi[1]catenane is prepared by a template-directed covalent strategy forcing backfolding macrocyclizations. All key steps towards the quasi[1]catenane, i.e., macrolactonization, CuAAC macrocyclizations and RCM towards a cycloolefin, worked well. Unfortunately, all attempts to hydrolyze the ketal liberating the [2]catenane architecture failed.

    2. Stereodefined Polysubstituted Enolates

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      Electrophilic Oxidation of Stereodefined Polysubstituted Silyl Ketone Aminals

      Jian Qiang Huang, Zackaria Nairoukh and Ilan Marek

      Version of Record online: 6 DEC 2017 | DOI: 10.1002/ejoc.201701516

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      We reported herein a practical approach to acyclic tertiary α-hydroxy carbonyl derivatives with excellent diastereoselectivity through a combined carbometalation-oxidation-silylation of alkynes followed by a second oxidation reaction of the resulting stereodefined polysubstituted silyl ketone aminals.

  13. Full Papers

    1. Directed ortho-Metalation

      Directed ortho-Metalation of Aryl Amides, O-Carbamates, and Methoxymethoxy Systems: Directed Metalation Group Competition and Cooperation

      M. A. Jalil Miah, Mukund P. Sibi, S. Chattopadhyay, Oluwole B. Familoni and Victor Snieckus

      Version of Record online: 5 DEC 2017 | DOI: 10.1002/ejoc.201701143

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      Competitive metalations with four directed metalation groups (DMGs) in comparison with the OCONEt2 DMG are extensively studied. The anionic ortho-Fries rearrangement, the double metalation–electrophile quench of carbamates, and iterative metalation procedures are reported. The results provide new routes for the synthesis 1,2,3- and 1,2,3,4-substituted aromatic derivatives for which comparison with known routes is made.

    2. Directed ortho-Metalation of O-Aryl N,N-Dialkylcarbamates: Methodology, Anionic ortho-Fries Rearrangement, and Lateral Metalation

      M. A. Jalil Miah, Mukund P. Sibi, S. Chattopadhyay, Oluwole B. Familoni and Victor Snieckus

      Version of Record online: 5 DEC 2017 | DOI: 10.1002/ejoc.201701142

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      The directed ortho-lithiation (DoM) reactions of O-aryl N,N-dialkylcarbamates are studied comprehensively and provide, by quenching with various electrophiles, a range of polysubstituted aromatic compounds. In addition, anionic ortho-Fries (AoF) rearrangements occur if the ortho-lithiated carbamates are warmed to room temperature in the absence of an external electrophile.

    3. C-H Activation

      Palladium Catalyzed Direct Acylation of Iodo-Acetanilides/Iodo-Phenyl Acetates: Domino One-Pot Synthesis of 2-Quinolinones

      Scuhand Basuli and Gedu Satyanarayana

      Version of Record online: 30 NOV 2017 | DOI: 10.1002/ejoc.201701250

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      Pd-catalyzed direct acylation reaction of iodoacetanilides/iodophenyl acetates with aldehydes is presented. Simple aldehydes were used as non-toxic acylating agents. This protocol comprises direct coupling with aldehydes without directing group assistance. The strategy was applied to a domino one-pot synthesis of 2-quinolinones through acylation and intramolecular aldol condensation.

  14. Communications

    1. Polycyclic Aromatic Heterocycles

      Triazacoronene Derivatives with Three peri-Benzopyrano Extensions: Synthesis, Structure, and Properties

      Bo Liu, Donghui Shi, Yihui Yang, Dayong Liu, Ming Li, Ernu Liu, Xiaogang Wang, Qiang Zhang, Mingyu Yang, Jing Li, Xianying Shi, Wenliang Wang and Junfa Wei

      Version of Record online: 30 NOV 2017 | DOI: 10.1002/ejoc.201701386

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      π-Extended triazacoronenes are synthesized by a one-pot process involving tandem triflic acid (TfOH)-catalyzed threefold Pictet–Spengler cyclization and K2CO3-catalyzed ipso-aromatic substitution. NMP = N-methylpyrrolidone.

  15. Microreviews

    1. Biomass

      Oleuropein: A Valuable Bio-Renewable Synthetic Building Block

      Lídia A. S. Cavaca and Carlos A. M. Afonso

      Version of Record online: 22 NOV 2017 | DOI: 10.1002/ejoc.201701136

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      Oleuropein has come to be seen as a potentially valuable natural compound for employment as a remarkable starting material for the generation of drug substances with new therapeutic utility. This microreview focuses on reported synthetic transformations of oleuropein, as well as on its structure and isolation, biosynthesis, biodegradation, and biological properties.

  16. Full Papers

    1. Conformation Analysis

      Structural and Computational Investigation of Intramolecular N···H Interactions in α- and β-Fluorinated 7-Azaindoline Amides

      Lennart Brewitz, Hidetoshi Noda, Naoya Kumagai and Masakatsu Shibasaki

      Version of Record online: 20 NOV 2017 | DOI: 10.1002/ejoc.201701083

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      Unusual intramolecular interactions between the 7-nitrogen and amide α-H atoms in fluorinated N1-acylated 7-azaindolines have been analyzed by experimental and computational means. As these intramolecular interactions also occur in non-fluorinated N1-acylated 7-azaindolines and similar heterocycles, this study is relevant to medicinal chemistry, potentially contributing to drug discovery programs.

    2. Detection of Nucleic Acids

      Synthesis and Applicability of Base-Discriminating DNA-Triplex-Forming 19F NMR Probes

      Naresh Bhuma, Ville Tähtinen and Pasi Virta

      Version of Record online: 10 OCT 2017 | DOI: 10.1002/ejoc.201701110

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      The detection of nucleobase content in DNA double helices has been demonstrated by triplex-forming probes. The applicability of two base-modified nucleosides, incorporated into the third strand, was evaluated. 19F NMR spectral finger prints depending on the nucleobase content could be obtained, which may find application to detect local environments of structurally resembling double-helical stretches.

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