European Journal of Organic Chemistry

Cover image for Vol. 2012 Issue 35

December 2012

Volume 2012, Issue 35

Pages 6811–6996

  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
      Efficient Catalysis of Aqueous Morita–Baylis–Hillman Reactions of Cyclic Enones by a Bicyclic Imidazolyl Alcohol (Eur. J. Org. Chem. 35/2012)

      Juliana C. Gomes, Manoel T. Rodrigues Jr., Albert Moyano and Fernando Coelho

      Version of Record online: 28 NOV 2012 | DOI: 10.1002/ejoc.201290096

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      The cover picture shows a Morita–Baylis–Hillman reaction between cyclic enones and aldehydes, catalyzed by a bicyclic imidazolyl alcohol and performed in water, the most eco-friendly solvent. The new bifunctional catalyst presents in its structure two key active centers: one acting as a Lewis base in association with a second one acting as a Brønsted acid. This synergic association seems to stabilize the zwitterionic species involved in the catalytic cycle of this synthetically useful chemical transformation. The new protocol avoids the use of phosphanes and has sustainable features. Details are discussed in the article by F. Coelho et al. on p. 6861 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
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correction
    1. Oxidative Carbonylation

      Oxidative Carbonylation as a Powerful Tool for the Direct Synthesis of Carbonylated Heterocycles (pages 6825–6839)

      Bartolo Gabriele, Raffaella Mancuso and Giuseppe Salerno

      Version of Record online: 26 SEP 2012 | DOI: 10.1002/ejoc.201200794

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      Recent developments in the application of oxidative carbonylation to the synthesis of carbonylated heterocycles are reviewed (coverage: 2006 to the beginning of 2012).

  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. Friedel–Crafts Acylation

      Friedel–Crafts Acylation Reactions Using Esters (pages 6841–6845)

      Subhash P. Chavan, Sumanta Garai, Achintya Kumar Dutta and Sourav Pal

      Version of Record online: 6 NOV 2012 | DOI: 10.1002/ejoc.201201181

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      Intermolecular and intramolecular Friedel–Crafts acylation reactions of various aliphatic and aromatic esters at room temperature with the use of very simple reagents and activating groups are described. The detailed mechanistic pathway was studied by DFT calculations and supported by experimental evidence.

    2. Glycosidation

      Intramolecular Glycosidation by Click Reaction Mediated Spacer Generation Followed by Spacer Cleavage (pages 6846–6851)

      Amit Kumar, Yiqun Geng and Richard R. Schmidt

      Version of Record online: 7 NOV 2012 | DOI: 10.1002/ejoc.201201076

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      The 1,2,3-triazole-forming click reaction was employed to generate glycosyl donor–spacer–acceptor constructs. Upon glycosidation, 14-membered macrocycles were obtained with high anomeric selectivity. Spacer cleavage was performed under Birch reduction conditions.

    3. C–S Bond Formation

      One-Pot Catalyst-Free Synthesis of β- and γ-Hydroxy Sulfides Using Diaryliodonium Salts and Microwave Irradiation (pages 6852–6855)

      Buchi Reddy Vaddula, Rajender S. Varma and John Leazer

      Version of Record online: 2 NOV 2012 | DOI: 10.1002/ejoc.201201313

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      A facile, one-pot, high-yielding protocol is described for the direct preparation of β- and γ-hydroxy sulfides from diaryliodonium salts, potassium thiocyanate, and ethane-1,2-diol/propane-1,3-diol without the need for a catalyst, base, or solvent.

    4. Ring-Opening Arylation

      Copper Powder Catalyzed Direct Ring-Opening Arylation of Benzazoles with Aryl Iodides in Polyethylene Glycol (pages 6856–6860)

      Lifang Yao, Qing Zhou, Wei Han and Shaohua Wei

      Version of Record online: 6 NOV 2012 | DOI: 10.1002/ejoc.201201166

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      The combination of copper powder with PEG-600 has been confirmed to be an expedient, efficient, and environmentally benign in situ nanocatalysis system for the direct ring-opening arylation of benzazoles with aryl iodides.

  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. Morita–Baylis–Hillman Reaction

      Efficient Catalysis of Aqueous Morita–Baylis–Hillman Reactions of Cyclic Enones by a Bicyclic Imidazolyl Alcohol (pages 6861–6866)

      Juliana C. Gomes, Manoel T. Rodrigues Jr., Albert Moyano and Fernando Coelho

      Version of Record online: 29 AUG 2012 | DOI: 10.1002/ejoc.201200950

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      A bicyclic imidazoyl compound was successfully used as a new bifunctional catalyst for the Morita–Baylis–Hillman reaction.

    2. Stereoelectronic Effects

      Conformationally Constrained Oxides of 1,3-Dithiane: Synthesis and NMR Spectroscopic Investigations (pages 6867–6877)

      Roland Ulshöfer, Tobias Wedel, Bastian Süveges and Joachim Podlech

      Version of Record online: 29 OCT 2012 | DOI: 10.1002/ejoc.201200675

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      Conformationally constrained derivatives of oxidised 1,3-dithianes (sulfides, sulfoxides, sulfones) have allowed an elucidation of stereoelectronic effects: 16 derivatives of dimethyl- and tert-butyl-1,3-dithianes and dithiadecalins were synthesised. Only 4J W couplings were observed in the 1H NMR spectra. A clear γ gauche effect of axial sulfoxides could not be proven from the 13C NMR spectra.

    3. Chiral Macrocycles

      Configurational Assignment of Cyclic Bisbibenzyls by HPLC-CD and Quantum-Chemical CD Calculations (pages 6878–6887)

      Anu Schaumlöffel, Matthias Groh, Michael Knauer, Andreas Speicher and Gerhard Bringmann

      Version of Record online: 29 OCT 2012 | DOI: 10.1002/ejoc.201200873

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      The chiroptical properties of atropo-enantiomeric plagiochins and riccardins are investigated by means of HPLC-CD in combination with quantum-chemical CD calculations. An increased degree of charge-transfer in the excited states makes the use of the coupled-cluster method mandatory to unambiguously determine the absolute configuration.

    4. Functionalized Phthalocyanines

      Synthesis and Copper(I)-Driven Disaggregation of a Zinc-Complexed Phthalocyanine Bearing Four Lateral Coordinating Rings (pages 6888–6894)

      Alexander G. Martynov, Yulia G. Gorbunova, Sergey E. Nefedov, Aslan Y. Tsivadze and Jean-Pierre Sauvage

      Version of Record online: 29 OCT 2012 | DOI: 10.1002/ejoc.201200944

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      A new phthalocyanine bearing four peripheral 1,10-phenanthroline-incorporating rings was prepared as an insoluble aggregate. After addition of copper(I), a monomolecular species was obtained, which shows good solubility. It has a folded and globular conformation originating from the interaction between the four lateral copper–1,10-phenanthroline complexes and the central phthalocyanine macrocycle.

    5. Macrocycles

      Synthesis of Cyclotriveratrylene–Phenylacetylene Derivatives and a Photophysical Investigation of Rigid Conjugated Cyclotriveratrylene Dendrimers (pages 6895–6903)

      Xiao-Na Han, Jian-Ming Chen, Zhi-Tang Huang and Qi-Yu Zheng

      Version of Record online: 2 NOV 2012 | DOI: 10.1002/ejoc.201201024

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      Cyclotriveratrylene (CTV) was functionalized by Sonogashira cross-coupling of CTV-I3 with a range of aryl-substituted alkynes. Among these novel macrocyclic derivatives, three star-like conjugated dendrimers with rigid macrocyclic cores display excellent photophysical properties.

    6. Polyketide Synthesis

      Converting a Birch Reduction Product into a Polyketide: Application to the Synthesis of a C1–C11 Building Block of Rimocidin (pages 6904–6923)

      Luc Nachbauer and Reinhard Brückner

      Version of Record online: 7 NOV 2012 | DOI: 10.1002/ejoc.201201112

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      An aromatic epoxide with a strong tendency for carbenium ion formation was ring-opened with inversion of configuration with EtCu(CN)Li. Birch reduction and ozonolysis transformed the resulting methoxyindane into a hydroxy-triketocarboxylic ester. Carbonyl group differentiation by dihydropyranone formation, diastereoselective C=O reductions, and thioketal formation delivered the target compound.

    7. Organocatalytic Domino Reactions

      Construction of Chiral Multi-Functionalized Polyheterocyclic Benzopyran Derivatives by Using an Asymmetric Organocatalytic Domino Reaction (pages 6924–6932)

      Zhi-Wei Guo, Xin-Sheng Li, Wei-Dong Zhu and Jian-Wu Xie

      Version of Record online: 29 OCT 2012 | DOI: 10.1002/ejoc.201200928

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      Chiral multi-functionalized polyheterocyclic benzopyran derivatives were easily obtained with excellent diastereoselectivities and good-to-excellent enantioselectivities from electron-deficient α,α-dicyano olefins and 3-nitro-2H-chromene derivatives under mild and simple conditions.

    8. Domino Reactions

      A Concise Domino Synthesis of Benzo-1,4-heterocycle Compounds via a Piancatelli/C–N Coupling/Michael Addition Process Promoted by La(OTf)3 (pages 6933–6939)

      Jinqian Liu, Qiang Shen, Jianjun Yu, Mengyun Zhu, Jianwei Han and Limin Wang

      Version of Record online: 2 NOV 2012 | DOI: 10.1002/ejoc.201200962

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      A La(OTf)3-catalyzed domino method has been developed to synthesize the cis-1,4-benzoxazine derivatives by a Piancatelli/C–N coupling/Michael addition process. A similar strategy was used to form 1,2,3,4-tetrahydroquinoxaline derivatives from 1 and N-substituted o-diaminobenzenes. This method should be valuable for the construction of heterocycles with biological and medicinal activities.

    9. Control of Regioselectivity

      Effects of the Pyridine 3-Substituent on Regioselectivity in the Nucleophilic Aromatic Substitution Reaction of 3-Substituted 2,6-Dichloropyridines with 1-Methylpiperazine Studied by a Chemical Design Strategy (pages 6940–6952)

      Peter Bach, Michaela Marczynke and Fabrizio Giordanetto

      Version of Record online: 2 NOV 2012 | DOI: 10.1002/ejoc.201200978

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      The regioselectivity of the nucleophilic aromatic substitution reactions of 3-substituted 2,6-dichloropyridines with 1-methylpiperazine as a function of R3 has been studied by a chemical design strategy and showed a statistically significant correlation with the Verloop steric parameter. A study of the solvent effect with R3 = CO2CH3 showed that the regioselectivity in 21 solvents was correlated with the solvatochromic β parameter.

    10. Small Ring Systems

      (E,E)-1,2,3,4-Tetracyclopropylbuta-1,3-diene: Synthesis and Some of Its Properties (pages 6953–6958)

      Armin de Meijere, Stefan Redlich, Sergei I. Kozhushkov, Dmitry S. Yufit, Jörg Magull, Denis Vidović, Heiko Schill and Henning Menzel

      Version of Record online: 30 OCT 2012 | DOI: 10.1002/ejoc.201201054

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      (E,E)-1,2,3,4-Tetracyclopropylbuta-1,3-diene and its 1,4-diiodinated derivative were prepared in 91 and 77 % yield, respectively. Their conformations were studied by X-ray crystal structure analysis. Differential scanning calorimetry measurements indicate that these compounds undergo significant internal reorganization on going from the liquid to the crystalline phase.

    11. Natural Products

      Asymmetric Synthesis of the C14–C26 Building Block of Eribulin Mesylate (pages 6959–6966)

      Akondi Srirama Murthy, Bodugum Mahipal and Srivari Chandrasekhar

      Version of Record online: 29 OCT 2012 | DOI: 10.1002/ejoc.201201119

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      The C14–C26 building block of eribulin mesylate is synthesized by using a tandem Sharpless asymmetric dihydroxylation, Julia–Kocienski olefination, Evans diastereoselective methylation and Maruoka allylation reaction as key transformations.

    12. Asymmetric Proton Sponges

      The Proton Sponge Effect: Substitution of Quino[7,8-h]quinoline and the First Structurally Characterised Derivatives (pages 6967–6975)

      Karl J. Shaffer, Daniel C. Parr, Marco Wenzel, Gareth J. Rowlands and Paul G. Plieger

      Version of Record online: 30 OCT 2012 | DOI: 10.1002/ejoc.201201131

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      A route to unsymmetrical derivatives of quino[7,8-h]quinoline was, and derivatives substituted in the 2,11-, 4,9- and 6,7-positions of quino[7,8-h]quinoline were synthesised. The syntheses, crystal structures and photophysical behaviours of a number of the derivatives is described.

    13. Radical Oxidation

      Mechanism and Scope of the MnIII-Initiated Oxidation of β-Ketocarbonyl Compounds: Furan Synthesis (pages 6976–6985)

      Chao Wang, Zhilong Li, Yeming Ju and Sangho Koo

      Version of Record online: 29 OCT 2012 | DOI: 10.1002/ejoc.201201194

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      The MnIII-initiated reaction pathway for the α-radical of β-keto ester 8c can be completely controlled to proceed through either radical cyclisation to give 15c under argon at 80 °C, or through oxidation/heterocyclisation to give 14c in the air at 50 °C, which provides a new synthetic method for furan derivatives.

    14. Glycomimetics

      Deoxythiosugar Derivatives with Furano, Pyrano, and Septano Motifs from L-Gulono-1,4-lactone and D-Glycero-D-gulo-heptono-1,4-lactone (pages 6986–6995)

      Thanikachalam Gunasundari and Srinivasan Chandrasekaran

      Version of Record online: 6 NOV 2012 | DOI: 10.1002/ejoc.201200906

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      The synthesis of thiosugar derivatives has been achieved using simple methods starting from aldonolactones, with the key reagent being benzyltriethylammonium tetrathiomolybdate, an effective sulfur-transfer reagent.

  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
      Diterpenes from European Euphorbia Species Serving as Prototypes for Natural-Product-Based Drug Discovery (page 6996)

      Andrea Vasas, Dóra Rédei, Dezső Csupor, Joseph Molnár and Judit Hohmann

      Version of Record online: 7 NOV 2012 | DOI: 10.1002/ejoc.201201411

      This article corrects:

      Diterpenes from European Euphorbia Species Serving as Prototypes for Natural-Product-Based Drug Discovery1

      Vol. 2012, Issue 27, 5115–5130, Version of Record online: 20 AUG 2012

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