European Journal of Organic Chemistry

Cover image for Vol. 2014 Issue 28

October 2014

Volume 2014, Issue 28

Pages 6089–6320

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
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      Organocatalytic Oxidation of Secondary Alcohols Using 1,2-Di(1-naphthyl)-1,2-ethanediamine (NEDA) (Eur. J. Org. Chem. 28/2014)

      Afnan Al-Hunaiti, Minna Räisänen, Petri Pihko, Markku Leskelä and Timo Repo

      Article first published online: 24 SEP 2014 | DOI: 10.1002/ejoc.201490078

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      The cover picture shows the organocatalytic oxidation of alcohols with high selectivity towards secondary alcohols. The reaction is catalyzed by 1,2-di(1-naphthyl)-1,2-ethanediamine (NEDA) in the presence of tert-butyl hydroperoxide (TBHP) as a terminal oxidant. The secondary benzyl alcohols and even hindered cycloaliphatic secondary alcohols are oxidized in nearly quantitative yields. Enantiomers of NEDA were also studied in the oxidative kinetic resolution of racemic secondary alcohols, and good to excellent ee values were observed. Details are discussed in the Short Communication by T. Repo et al. on p. 6141 ff.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
    1. Graphical Abstract: Eur. J. Org. Chem. 28/2014 (pages 6089–6096)

      Article first published online: 24 SEP 2014 | DOI: 10.1002/ejoc.201490080

  3. News

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

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

      Progress in Catalytic Asymmetric Protonation (pages 6103–6119)

      Sylvain Oudeyer, Jean-François Brière and Vincent Levacher

      Article first published online: 22 MAY 2014 | DOI: 10.1002/ejoc.201402213

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      This review provides an overview of recent advances in catalytic enantioselective protonation of preformed enol derivatives and catalytically generated enolates or equivalents through various cascade reaction sequences giving access to a large range of enantioenriched compounds containing tertiary stereocentres.

    2. Task-Specific Ionic Liquids

      Point-Functionalization of Ionic Liquids: An Overview of Synthesis and Applications (pages 6120–6139)

      Cinzia Chiappe and Christian Silvio Pomelli

      Article first published online: 27 JUN 2014 | DOI: 10.1002/ejoc.201402093

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      The versatility of ionic liquids can be conveniently exploited by introducing specific functional groups at selected positions of the cation or anion. These salts (task-specific ionic liquids) can be synthesized through simple and straightforward procedures.

  5. Short Communications

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

      Organocatalytic Oxidation of Secondary Alcohols Using 1,2-Di(1-naphthyl)-1,2-ethanediamine (NEDA) (pages 6141–6144)

      Afnan Al-Hunaiti, Minna Räisänen, Petri Pihko, Markku Leskelä and Timo Repo

      Article first published online: 27 AUG 2014 | DOI: 10.1002/ejoc.201402991

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      A nonmetal catalytic oxidation of alcohols with preferential oxidation of secondary alcohols by diamine is developed. 1,2-Di(1-naphthyl)-1,2-ethanediamine (NEDA) is used as catalyst to selectively oxidize secondary alcohols in the presence of TBHP as terminal oxidant. The chiral NEDA is also studied and shows promising enantioselectivity in oxidative kinetic resolution of racemic secondary alcohols with good to excellent ee values.

    2. Fluorine-18-Labelled Radiotracers

      An Efficient Method for Enhancing the Reactivity and Flexibility of [18F]Fluoride Towards Nucleophilic Substitution Using Tetraethylammonium Bicarbonate (pages 6145–6149)

      Laurent Brichard and Franklin I. Aigbirhio

      Article first published online: 29 AUG 2014 | DOI: 10.1002/ejoc.201402587

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      Tetraethylammonium hydrogen carbonate proves to be a very efficient phase-transfer agent for the enhancement of the reactivity of [18F]fluoride towards nucleophilic substitution reactions with or without low amounts of water.

    3. Stereoselective Nucleophilic Addition

      Highly Stereoselective Nucleophilic Addition of Difluoromethyl-2-pyridyl Sulfone to Sugar Lactones and Efficient Synthesis of Fluorinated 2-Ketoses (pages 6150–6154)

      Xiao Liu, Qiang Yin, Jian Yin, Guohua Chen, Xin Wang, Qi-Dong You, Yue-Lei Chen, Bing Xiong and Jingkang Shen

      Article first published online: 29 AUG 2014 | DOI: 10.1002/ejoc.201402757

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      Nucleophilic addition of difluoromethyl-2-pyridyl sulfone to sugar lactones gave intermediates that are stable and capable of useful conversions. Formal elimination of the anomeric hydroxy and sulfonyl groups yielded a 1-deoxy-1-difluoromethylene mannopyranose derivative. Fluorinated 2-ketose analogues were prepared by a one-pot reduction with allylmagnesium chloride.

  6. Full Papers

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

      Linear Oligocarbazole-Based Organogelators: Synthesis and Fluorescent Probing of Explosives (pages 6155–6162)

      Guanghui Hong, Chong Qian, Pengchong Xue, Xingliang Liu, Qingqing Wang, Mingyang Liu, Peng Gong and Ran Lu

      Article first published online: 18 AUG 2014 | DOI: 10.1002/ejoc.201402565

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      The first simple carbazole-based organogelator C1 has been synthesized and can self-assemble into nanofibers through π–π interactions. Moreover, the new linear carbazole-based trimer C3 and pentamer C5 with extended conjugation also formed gels in some organic solvents upon ultrasound stimulation, and blue-emitting nanofibers based on C3 detected vapors of TNT and DNT by fluorescent quenching.

    2. Two-Photon Chromophores

      Synthesis and Two-Photon Absorption Properties of Ladder-Type Chromophores with Functionalized Pyrazine Units Fused as the End-Groups (pages 6163–6174)

      Tzu-Chau Lin, Bo-Kai Tsai, Yi-You Liu and Ming-Yu Tsai

      Article first published online: 14 AUG 2014 | DOI: 10.1002/ejoc.201402622

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      Three multipolar chromophores based on ladder-type units as the central π-bridges with functionalized pyrazine moieties fused as the end-groups were synthesized for study of two-photon absorption (2PA). The π-conjugation length of the central oligo-p-phenylene component is closely related to the magnitude of 2PA, and such a structural motif provides access to highly efficient nonlinear absorbers.

    3. Synthetic Methods

      Development and Optimization of Simple One-Step Methods for the Synthesis of 4-Amino-Substituted 1,8-Naphthalimides (pages 6175–6182)

      Tomas Kindahl, Elin Chorell and Erik Chorell

      Article first published online: 20 AUG 2014 | DOI: 10.1002/ejoc.201402684

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      One-step methods for the synthesis of 4-amino-substituted 1,8-naphthalimides have been developed and optimized by using multivariate studies of temperature, reaction time and equivalents of substrates. The identified conditions could successfully be applied to generate various 4-amino-substituted 1,8-naphthalimides in high yields.

    4. Natural Product Reassignment

      Toward the Total Synthesis of Klaivanolide: Complete Reinterpretation of Its Originally Assigned Structure (pages 6183–6189)

      Laurent Ferrié, Sabrina Ferhi, Guillaume Bernadat and Bruno Figadère

      Article first published online: 20 AUG 2014 | DOI: 10.1002/ejoc.201402741

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      Attempts towards the total synthesis of uncommon seven-membered ring lactone klaivanolide led us to revise its original structural assignment. The isolated compound was revealed to be a known molecule, the five-membered ring acetylmelodorinol.

    5. Asymmetric Catalysis

      Organocatalytic Enantioselective Strecker Reaction of Imines Containing a Thiazole Moiety by Using a Cinchona-Based Squaramide Catalyst (pages 6190–6199)

      Hai-Xiao He and Da-Ming Du

      Article first published online: 21 AUG 2014 | DOI: 10.1002/ejoc.201402764

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      An organocatalytic enantioselective Strecker reaction was developed for the synthesis of α-amino nitriles that contain a thiazole moiety by using a cinchona-based squaramide catalyst. The corresponding products were obtained in good to excellent yields (up to 99 %) with excellent enantioselectivities (up to 98 % ee) by starting from aromatic-substituted imines.

    6. Enzymatic Transesterification

      Diesterification of 3-[(β-Cyclodextrinyl)succinamido]propane-1,2-diol Catalysed by Lipase: Diastereoselectivity or Tridimensional Substrate Specificity? (pages 6200–6209)

      Cédric Gervaise, Véronique Bonnet, Florian Nolay, Christine Cézard, Imane Stasik, Catherine Sarazin and Florence Djedaïni-Pilard

      Article first published online: 20 AUG 2014 | DOI: 10.1002/ejoc.201402414

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      Two diastereoisomers of 3-[(β-cyclodextrinyl)succinamido]propane-1,2-diol have been transesterified with fatty esters and immobilized lipase from Mucor miehei. They react with different conversions, contrary to their analogues without cyclodextrins. The hydrogen bonds in the three-dimensional structures, which account for this phenomenon, are revealed by molecular modelling and NMR studies.

    7. Heterocyclic Ketene Aminals

      Isomerization of Ninhydrin–Heterocyclic Ketene Aminal Adducts: Kinetic versus Thermodynamic Control, Solvent Dependency and Mechanism (pages 6210–6218)

      Nanyang Chen, Minming Zou, Xue Tian, Fengjuan Zhu, Danping Jiang, Jiagao Cheng, Xusheng Shao and Zhong Li

      Article first published online: 20 AUG 2014 | DOI: 10.1002/ejoc.201402677

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      The first example of isomerization of ninhydrin–heterocyclic ketene aminals adducts is reported. The isomerization shows large solvent dependency and provides an efficient method with which to access hitherto undisclosed indeno[2,1-b]pyrrol-8(1H)-ones. Reaction products can now be regulated based on kinetic and thermodynamic selection principles.

    8. Fused Heterocycles

      A K2CO3-Mediated Regioselective Synthesis of Indole/Pyrrole-Fused 1,4-Oxazines: An Unexpected Indole-Fused Azlactone Synthesis (pages 6219–6226)

      Jaya Kishore Vandavasi, Wan-Ping Hu, Gopal Chandru Senadi, Siva Senthil Kumar Boominathan, Hsing-Yin Chen and Jeh-Jeng Wang

      Article first published online: 22 AUG 2014 | DOI: 10.1002/ejoc.201402818

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      A regioselective, base-catalyzed 6-exo-dig cyclization has been developed for the synthesis of indole- and pyrrole-fused 1,4-oxazines. In addition, an unprecedented one-pot hydroamination reaction was observed to occur with high chemo- and regioselectivity in the presence of base to afford indole-fused azlactones.

    9. Maillard-Type Condensation

      Synthesis of the Revised Structure of Acortatarin A (pages 6227–6241)

      Hui Min Geng, Louise A. Stubbing, Jack Li-yang Chen, Daniel P. Furkert and Margaret A. Brimble

      Article first published online: 25 AUG 2014 | DOI: 10.1002/ejoc.201403000

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      The use of a novel Maillard-type condensation between a primary amine derived from D-mannitol and a dihydropyranone as a key step to access the unusual morpholine-spiroketal acortatarin A is reported. The approach also allows access to a C-2 analogue, and can be used for synthesis of related 2-formylpyrrole natural products.

    10. Silica-Supported Catalysts

      Rhodium-NHC Hybrid Silica Materials as Recyclable Catalysts for [2+2+2] Cycloaddition Reactions of Alkynes (pages 6242–6251)

      Martí Fernández, Meritxell Ferré, Anna Pla-Quintana, Teodor Parella, Roser Pleixats and Anna Roglans

      Article first published online: 20 AUG 2014 | DOI: 10.1002/ejoc.201402649

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      Hybrid silica materials derived from rhodium(I) complexes bearing an N-heterocyclic carbene ligand are obtained either by sol-gel or grafting processes. The materials are fully characterized by solid state NMR, N2-sorption measurements, thermogravimetric analysis and elemental analysis; their catalytic activity and recyclability are also evaluated in the [2+2+2] cycloaddition of alkynes.

    11. Fullerene Derivatives

      Reactions of [60]Fullerene with Halides and Amino Acids to Synthesize Fulleropyrrolidines (pages 6252–6262)

      Bo Jin, Juan Shen, Rufang Peng, Congdi Chen and Shijin Chu

      Article first published online: 14 AUG 2014 | DOI: 10.1002/ejoc.201402655

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      Fulleropyrrolidines bearing ArCH moieties were obtained in reactions between C60, the appropriate benzyl chlorides, and amino acids. A detailed investigation of these reactions resulted in the discovery of other halides, such as allyl chlorides, propargyl bromides, ethyl bromoacetate, bromoacetonitrile, and alkyl bromides, that also reacted with C60 and amino acids to produce fulleropyrrolidines.

    12. Regioselectivity Switching

      Palladium-Catalyzed Regioselective 5-exo-O-Cyclization/Oxidative Heck Cascades from o-Alkynylbenzamides and Electron-Deficient Alkenes (pages 6263–6271)

      Youssef Madich, Rosana Álvarez and José M. Aurrecoechea

      Article first published online: 15 AUG 2014 | DOI: 10.1002/ejoc.201402709

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      Oxycyclization/oxidative Heck cascade reactions between o-alkynylbenzamides and electron-deficient alkenes have a cyclization regiochemistry that is catalyst dependent. Thus, the 6-endo-regioselectivity reported for a PdCl2(PPh3)2 catalyst becomes a preference for 5-exo-products when Pd(OAc)2 is used.

    13. Natural Product Synthesis

      Flexible Synthesis of Planar Chiral Azoninones and Optically Active Indolizidinones (pages 6272–6284)

      Frank Bohland, Irina Erlin, Lukas Platte, Maike Schröder, Dieter Schollmeyer and Udo Nubbemeyer

      Article first published online: 21 AUG 2014 | DOI: 10.1002/ejoc.201402720

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      L-Proline derivatives were used to synthesise optically active 2-vinylpyrrolidines with E and Z double bonds. Zwitterionic aza-Claisen rearrangements led to planar chiral azoninones with defined configurations, which served as key intermediates for the synthesis of indolizidinones with up to five stereogenic centres.

    14. Atroposelectivity

      A Concise Atroposelective Formal Synthesis of (–)-Steganone (pages 6285–6294)

      Boubacar Yalcouye, Sabine Choppin, Armen Panossian, Frédéric R. Leroux and Françoise Colobert

      Article first published online: 21 AUG 2014 | DOI: 10.1002/ejoc.201402761

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      A highly atroposelective formal synthesis of (–)-steganone is described highlighting the use of an enantiopure sulfoxide as a chiral auxiliary in the Suzuki–Miyaura cross-coupling reaction.

    15. Star-Shaped Compounds

      Modular Syntheses of Star-Shaped Pyridine, Bipyridine, and Terpyridine Derivatives by Employing Sonogashira Reactions (pages 6295–6302)

      Daniel Trawny, Valentin Kunz and Hans-Ulrich Reissig

      Article first published online: 21 AUG 2014 | DOI: 10.1002/ejoc.201402778

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      Modular, simple, and efficient! A library of C3-symmetrical compounds with benzene cores and pyridine, bipyridine, and terpyridine end groups were prepared from simple precursors.

    16. Perfluoroalkylation

      A General, Regiospecific Synthetic Route to Perfluoroalkylated Arenes via Arenediazonium Salts with RFCu(CH3CN) Complexes (pages 6303–6309)

      Dong-Fang Jiang, Chao Liu, Yong Guo, Ji-Chang Xiao and Qing-Yun Chen

      Article first published online: 15 AUG 2014 | DOI: 10.1002/ejoc.201402820

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      Acetonitrile is used as a ligand to stabilize perfluorocopper species by forming RFCu(CH3CN) complexes. Arenediazonium salts successfully react with this complex, leading to the regiospecific perfluoroalkylation of arenes. A wide range of functional groups are tolerated in the reaction.

    17. Total Synthesis

      Total Synthesis of a Pyrrole Lactone Alkaloid, Longanlactone (pages 6310–6313)

      Chada Raji Reddy, Motatipally Damoder Reddy and Uredi Dilipkumar

      Article first published online: 15 AUG 2014 | DOI: 10.1002/ejoc.201402563

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      The first total synthesis of a new pyrrole lactone alkaloid, longanlactone, along with its C-4 epimer is achieved from the natural amino acid L-aspartic acid with a Barbier-type propargylation and a Paal–Knorr pyrrole synthesis as key steps.

    18. Cytotoxic Nucleosides

      Trifluoromethylated Nucleosides: A Building Block Approach to Cytotoxic Adenosine Analogues (pages 6314–6320)

      Johannes Drexler and Ulrich Groth

      Article first published online: 20 AUG 2014 | DOI: 10.1002/ejoc.201402755

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      Adenosine analogues based on the 7-deazapurine motif were synthesized using synthons, allowing for introduction of a diverse set of substituents, including fluorinated moieties. Analogue cytotoxicities were determined against HeLa S3 and Hep G2 cancer cell lines and compared with the structurally similar agent tubercidin; one lead structure with nM bioactivity was identified.

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