European Journal of Organic Chemistry

Cover image for Vol. 2017 Issue 12

March 27, 2017

Volume 2017, Issue 12

Pages 1566–1646

  1. Front Cover

    1. Top of page
    2. Front Cover
    3. Microreview
    4. Communications
    5. Full Papers
    6. Communications
    7. Full Papers
    8. Communications
    9. Full Papers
    1. You have free access to this content
      Front Cover: Methylsulfenylation of Electrophilic Carbon Atoms: Reaction Development, Scope, and Mechanism (Eur. J. Org. Chem. 12/2017) (page 1566)

      Adriane A. Pereira, Amanda S. Pereira, Amanda C. de Mello, Arthur G. Carpanez, Bruno A. C. Horta and Giovanni W. Amarante

      Version of Record online: 23 MAR 2017 | DOI: 10.1002/ejoc.201700354

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      The cover picture shows a chemoselective C–S bond formation through a metal-free process under microwave irradiation. The methylsulfenylation of electrophilic carbons is possible by using cheap and commercially available dimethylsulfoxide. Under the optimized reaction conditions, chalcone, dibenzylideneacetone, as well as Morita–Baylis–Hillman adduct derivatives were successfully sulfenylated. Deoxygenation of DMSO and nucleophilic addition of a sulphur intermediate are the key steps for this process. Details are discussed in the Communication by B. A. C. Horta, G. W. Amarante et al. on page 1578 ff (DOI: 10.1002/ejoc.201601613).

  2. Microreview

    1. Top of page
    2. Front Cover
    3. Microreview
    4. Communications
    5. Full Papers
    6. Communications
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    8. Communications
    9. Full Papers
    1. Natural Product Synthesis

      Strategies for the Synthesis of the Halenaquinol and Xestoquinol Families of Natural Products (pages 1567–1577)

      Gregg M. Schwarzwalder and Christopher D. Vanderwal

      Version of Record online: 16 FEB 2017 | DOI: 10.1002/ejoc.201601418

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      The wealth of different strategies for the chemical synthesis of the halenaquinol/xestoquinol family of natural products is discussed. Similar themes throughout the different achievements are highlighted, and a discussion of the recently discovered relative exiguaquinol is included.

  3. Communications

    1. Top of page
    2. Front Cover
    3. Microreview
    4. Communications
    5. Full Papers
    6. Communications
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    8. Communications
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    1. Organocatalysis

      Methylsulfenylation of Electrophilic Carbon Atoms: Reaction Development, Scope, and Mechanism (pages 1578–1582)

      Adriane A. Pereira, Amanda S. Pereira, Amanda C. de Mello, Arthur G. Carpanez, Bruno A. C. Horta and Giovanni W. Amarante

      Version of Record online: 27 JAN 2017 | DOI: 10.1002/ejoc.201601613

      Thumbnail image of graphical abstract

      The methylsulfenylation of activated carbons is now possible by using DMSO. A combined metal-free process and microwave irradiation allow chemoselective C–S bond formation.

  4. Full Papers

    1. Top of page
    2. Front Cover
    3. Microreview
    4. Communications
    5. Full Papers
    6. Communications
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    8. Communications
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    1. Rotaxanes

      Rotamer-Induced Dynamic Nature of a [2]Rotaxane and Control of the Dynamics by External Stimuli (pages 1583–1593)

      Saikat Santra and Pradyut Ghosh

      Version of Record online: 27 MAR 2017 | DOI: 10.1002/ejoc.201601525

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      A new [2]rotaxane based on a tris(amino) ether macrocyclic wheel is functionalized with three tertiary amide groups and exhibits dynamic behaviour through rotamer formation as well as locking and unlocking properties in the presence of Na+ ions and 18-crown-6 inputs, respectively.

    2. Polycycle Synthesis

      Straightforward Synthesis of a Vicinal Double-Bridgehead Iodo Trimethylsilyl Octacycle: Unprecedented Lack of Reactivity of the Silyl Group in the Presence of Fluoride Anions (pages 1594–1603)

      Pelayo Camps, David Lozano, Enrique Guitián, Diego Peña, Dolores Pérez, Mercè Font-Bardia and Antonio L. Llamas-Saíz

      Version of Record online: 27 MAR 2017 | DOI: 10.1002/ejoc.201601618

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      Double-domino nucleophilic substitution/intramolecular Diels–Alder reaction of a bicyclic precursor gave an iodo trimethylsilyl octacycle. Subsequent generation of a pyramidalized alkene with different fluoride sources failed, whereas Pd0-catalyzed cocyclotrimerization occurred chemo- and stereoselectively. Aromatization took place with CsF while AgF lead to the corresponding fluoride compound.

  5. Communications

    1. Top of page
    2. Front Cover
    3. Microreview
    4. Communications
    5. Full Papers
    6. Communications
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    1. Cyclization

      Palladium-Catalyzed 3-Aryl-5-acyl-1,2,4-thiadiazole Formation from Ketones, Amidines, and Sulfur Powder (pages 1604–1607)

      Zilong Wang, Hao Xie, Fuhong Xiao, Yanjun Guo, Huawen Huang and Guo-Jun Deng

      Version of Record online: 27 MAR 2017 | DOI: 10.1002/ejoc.201700148

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      An efficient strategy to prepare 3,5-disubstituted 1,2,4-thiadiazoles from ketones, amidines, and sulfur powder under palladium-catalyzed conditions is developed. Aromatic ketones act as the carbon and acyl sources in this transformation. This reaction provides efficient access to 3-aryl-5-acyl-1,2,4-thiadiazoles from readily available starting materials.

  6. Full Papers

    1. Top of page
    2. Front Cover
    3. Microreview
    4. Communications
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    6. Communications
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    1. Artificial Photosynthesis

      Synthesis of a Chlorin Fullerene Dyad for Artificial Photosynthesis (pages 1608–1617)

      Jordi Cerón Bertran and Franz-Peter Montforts

      Version of Record online: 28 MAR 2017 | DOI: 10.1002/ejoc.201601504

      Thumbnail image of graphical abstract

      A chlorin diene subunit was linked to fullerene C60 by means of a Diels–Alder reaction. The rigid architecture of the new dyad was designed for investigation of light-induced electron transfer in a conformationally restricted chlorin donor fullerene acceptor system.

    2. Host-Guest cChemistry

      Synthesis of Water-Soluble Triazinophanes and Evaluation of Their Molecular Recognition Properties (pages 1618–1623)

      Shuhei Kusano, Sae Konishi, Ryuta Ishikawa, Norihiro Sato, Satoshi Kawata, Fumi Nagatsugi and Osamu Hayashida

      Version of Record online: 28 MAR 2017 | DOI: 10.1002/ejoc.201601663

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      Three water-soluble triazinophanes have been developed. The exploration of host–guest properties in aqueous media revealed that the guest recognition properties could be modulated through the post-modification of the triazine rings

  7. Communications

    1. Top of page
    2. Front Cover
    3. Microreview
    4. Communications
    5. Full Papers
    6. Communications
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    8. Communications
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    1. Isomerization–Addition Cascade

      Addition of Primary Amines to 2-(1-Alkynyl)-2-cycloalken-1-ones (pages 1624–1627)

      Aurelija Urbanaitė, Lukas Šteinys, Algirdas Brukštus and Inga Čikotienė

      Version of Record online: 28 MAR 2017 | DOI: 10.1002/ejoc.201700119

      Thumbnail image of graphical abstract

      The regio- and stereoselective nucleophilic addition of primary aliphatic amines to 2-(1-alkynyl)-2-cycloalken-1-ones proceeds through double-bond migration. In particular, (Z)-β-enaminones having cycloalkene rings can be prepared through a mild and atom-economical route.

  8. Full Papers

    1. Top of page
    2. Front Cover
    3. Microreview
    4. Communications
    5. Full Papers
    6. Communications
    7. Full Papers
    8. Communications
    9. Full Papers
    1. Asymmetric Catalysis

      Enantioselective Aromatic Sulfide Oxidation and Tandem Kinetic Resolution Using Aqueous H2O2 and Chiral Iron–Bis(oxazolinyl)bipyridine Catalysts (pages 1628–1637)

      Angela Jalba, Noémie Régnier and Thierry Ollevier

      Version of Record online: 29 MAR 2017 | DOI: 10.1002/ejoc.201601597

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      An enantioselective oxidation of aromatic sulfides has been developed by using aqueous H2O2, FeCl2, and the chiral 6,6′-bis(4-isopropyloxazolin-2-yl)-2,2′-bipyridine (bipybox-iPr) ligand. The corresponding sulfoxides were obtained with high enantioselectivities and in good yields.

    2. Organocatalysts

      Hybrid-Type Squaramide-Fused Amino Alcohol Organocatalysts for Enantioselective Nitro-Aldol Reaction of Nitromethane with Isatins (pages 1638–1646)

      Madhu Chennapuram, U. V. Subba Reddy, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Mitsuhiro Takeshita and Hiroto Nakano

      Version of Record online: 29 MAR 2017 | DOI: 10.1002/ejoc.201700138

      Thumbnail image of graphical abstract

      Hybrid-type squaramide-fused amino alcohol organocatalysts were synthesized, and their catalytic efficiency in the asymmetric nitro-aldol reaction of nitromethane and isatin derivatives was investigated. This transformation successfully afforded chiral 3-alkyl-substituted 3-hydroxyoxindoles in excellent yields with high enantioselectivities.

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