European Journal of Organic Chemistry

Cover image for Vol. 2014 Issue 24

August 2014

Volume 2014, Issue 24

Pages 5103–5378

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Full Paper
    7. Short Communications
    8. Full Papers
    9. Correction
    1. Selective Synthesis of Tetrasubstituted 4-(Tetrazol-5-yl)-1H-imidazoles from 2-(Tetrazol-5-yl)-2H-azirines (Eur. J. Org. Chem. 24/2014)

      Ana Lúcia Cardoso, Américo Lemos and Teresa M. V. D. Pinho e Melo

      Article first published online: 12 AUG 2014 | DOI: 10.1002/ejoc.201490066

      Thumbnail image of graphical abstract

      The cover picture shows the selective synthesis of new 4-(tetrazol-5-yl)-1H-imidazoles by Zn(OTf)2-catalyzed reaction of 2-(tetrazol-5-yl)-2H-azirines with imines. The synthetic methodology enabled the synthesis of a wide range of multi-substituted 4-(tetrazol-5-yl)-1H-imidazoles, which can be regarded as isosteres of 1H-imidazole-4-carboxylic acid derivatives, a class of compounds with interesting biological properties, namely anti-tuberculosis activity. Details are discussed in the article by T. M. V. D. Pinho e Melo et al. on p. p. 5159 ff. The authors thank Paulo Sanches for his contribution in designing the cover picture.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Full Paper
    7. Short Communications
    8. Full Papers
    9. Correction
    1. Graphical Abstract: Eur. J. Org. Chem. 24/2014 (pages 5103–5110)

      Article first published online: 12 AUG 2014 | DOI: 10.1002/ejoc.201490068

  3. News

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

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Full Paper
    7. Short Communications
    8. Full Papers
    9. Correction
    1. Functionalization of Imidazo[1,2-a]pyridines by Means of Metal-Catalyzed Cross-Coupling Reactions (pages 5119–5138)

      Jamal Koubachi, Saïd El Kazzouli, Mosto Bousmina and Gérald Guillaumet

      Article first published online: 18 JUN 2014 | DOI: 10.1002/ejoc.201400065

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      The latest developments in the field of imidazo[1,2-a]pyridine functionalization by means of cross-coupling reactions such as the Sonogashira, Heck, Negishi, Suzuki–Miyaura, and Stille reactions, as well as by C-arylation, C-alkenylation, carbonylation, and double functionalization, are reviewed and discussed.

  5. Full Paper

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

      Highly Enantioselective Construction of Spirocyclopentaneoxindoles Containing Four Consecutive Stereocenters through an Organocatalytic Iminium–Enamine Cascade Reaction (pages 5139–5143)

      Liang-Zhong Ding, Tong-Sheng Zhong, Hao Wu and Yong-Mei Wang

      Article first published online: 23 JUL 2014 | DOI: 10.1002/ejoc.201402687

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      Biologically important and synthetically challenging spirocyclopentaneoxindole derivatives containing four consecutive stereocenters, including one spiro quaternary center, are constructed with excellent enantio- and diastereomeric purities by an organocatalytic iminium–enamine cascade sequence between 3-substituted bifunctional oxindoles and α,β-unsaturated aldehydes under mild conditions.

  6. Short Communications

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

      Electrochemical Deoxygenation of Aromatic Amides and Sulfoxides (pages 5144–5148)

      Carolin Edinger and Siegfried R. Waldvogel

      Article first published online: 22 JUL 2014 | DOI: 10.1002/ejoc.201402714

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      The electrochemical deoxygenation of a broad range of aromatic carboxamides is achieved under mild conditions. Furthermore, sulfides can be readily prepared by subjecting the corresponding sulfoxides to the elaborated electroreductive strategy.

    2. Heterocycles

      Synthesis of 1,2,4-Thiadiazoles by Oxidative Dimerization of Carbothioamides by Using Oxone (pages 5149–5152)

      Akira Yoshimura, Anthony D. Todora, Brent J. Kastern, Steven R. Koski and Viktor V. Zhdankin

      Article first published online: 23 JUL 2014 | DOI: 10.1002/ejoc.201402756

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      1,2,4-Thiadiazoles are efficiently synthesized in good yields through the oxidative dimerization of carbothioamides by using Oxone as a readily available, inexpensive, and environmentally safe oxidant.

    3. Cross-Coupling

      Efficient One-Pot Cross-Coupling of Two Aryl Halides by Stannylation/Stille Reaction in Water under Microwave Irradiation (pages 5153–5157)

      Xin Tan, Zi Jie Zhou, Jia Xin Zhang and Xin Hong Duan

      Article first published online: 15 JUL 2014 | DOI: 10.1002/ejoc.201402404

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      A one-pot cross-coupling of two aryl halides by stannylation/Stille reaction is reported. This approach includes the elimination of isolation/purification steps of the aryl stannanes, and the combined use of microwave heating and water as a single solvent makes this protocol simple, step economical, and highly efficient for the synthesis of a wide range of biaryls.

  7. Full Papers

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

      Selective Synthesis of Tetrasubstituted 4-(Tetrazol-5-yl)-1H-imidazoles from 2-(Tetrazol-5-yl)-2H-azirines (pages 5159–5165)

      Ana Lúcia Cardoso, Américo Lemos and Teresa M. V. D. Pinho e Melo

      Article first published online: 24 JUN 2014 | DOI: 10.1002/ejoc.201402559

      Thumbnail image of graphical abstract

      The zinc trifluoromethanesulfonate [Zn(OTf)2] catalyzed reaction of 2-(tetrazol-5-yl)-2H-azirines with imines is explored. This method offers the selective synthesis of a wide range of new unsymmetrically 1,2,4,5-tetrasubstituted imidazoles, which are molecules with potential relevance in medicinal chemistry. PNB = p-nitrobenzyl.

    2. Fluorine Migration

      Fluoro-Ene Reaction Versus [2+2] Cycloaddition in the Thermal C2–C6 Cyclization of Enyne-Allenes: An Experimental and Theoretical Investigation (pages 5166–5177)

      M. Emin Cinar, Chandrasekhar Vavilala, Ralph Jaquet, Jan W. Bats and Michael Schmittel

      Article first published online: 17 JUL 2014 | DOI: 10.1002/ejoc.201402438

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      [1,5]-Fluorine migration has been attempted by using σ,π-diradical intermediate generated by the thermal C2–C6 (Schmittel) cyclization of enyne-allenes that have a fluorine atom proximate to the allene terminus. DFT calculations, including potential energy surfaces, shed light on this intriguing fluorine shift.

    3. Atropisomerism

      Synthesis and Characterisation of 1,7-Di- and Inherently Chiral 1,12-Di- and 1,6,7,12-Tetraarylperylenetetracarbox-3,4:9,10-diimides (pages 5178–5195)

      Bernard Pagoaga, Louis Giraudet and Norbert Hoffmann

      Article first published online: 15 JUL 2014 | DOI: 10.1002/ejoc.201402625

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      Perylene bisimide derivatives possessing aryl substituents in the bay positions have been synthesised and characterised, including the inherently chiral C2 and D2 symmetric derivatives. Pure enantiomers have been prepared.

    4. Nitrogen and Oxygen Heterocycles

      N-Acyl-N-tosylhydrazine as a Synthon To Construct Tetrasubstituted Carbon Centers Possessing a Nitrogen Group (pages 5196–5203)

      Kosuke Namba, Yoshihiro Shobo, Kazuki Fujimoto, Isamu Shoji, Masahiro Yoshida and Keiji Tanino

      Article first published online: 17 JUL 2014 | DOI: 10.1002/ejoc.201402650

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      New halohydrazidation and hydrazidopalladation reactions were developed that use the synthon N-acyl-N-tosylhydrazine. The intramolecular bromohydrazidation reactions of β,γ-unsaturated N-acyl-N-tosylhydrazines gave pyrazolidinone ring systems. The intramolecular hydrazidopalladation reactions of γ,δ-unsaturated N-acyl-N-tosylhydrazine afforded hydropyridazine ring systems.

    5. Circular Dichroism

      Determination of the Stereostructure of Pyrimidine Nucleoside Derivatives with a Combination of Various Chiroptical Methods (pages 5204–5213)

      Marcin Górecki, Aleksandra Karczmarska-Wódzka, Renata Kołodziejska, Marcin Dramiński and Jadwiga Frelek

      Article first published online: 15 JUL 2014 | DOI: 10.1002/ejoc.201402190

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      The absolute configuration of pyrimidine nucleoside derivatives obtained by enantioselective reduction was determined using a combination of electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopy in tandem with quantum chemical calculations.

    6. Heterocyclic Couplings

      Triarylbismuthanes as Threefold Aryl-Transfer Reagents in Regioselective Cross-Coupling Reactions with Bromopyridines and Quinolines (pages 5214–5228)

      Maddali L. N. Rao and Ritesh J. Dhanorkar

      Article first published online: 15 JUL 2014 | DOI: 10.1002/ejoc.201402455

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      Cross-couplings of bromopyridines and bromoquinolines using triarylbismuth reagents have been carried out under palladium-catalysed conditions. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-coupling products were formed regioselectively in good to high yields.

    7. Carbocycles

      Stereoselective Synthesis of Enantiopure Oxetanes, a Carbohydrate Mimic, an ϵ-Lactone, and Cyclitols from Biocatalytically Derived β-Hydroxy Esters as Chiral Precursors (pages 5229–5246)

      Debabrata Das, Joydev Halder, Rajib Bhuniya and Samik Nanda

      Article first published online: 15 JUL 2014 | DOI: 10.1002/ejoc.201402521

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      Several enantiopure α-substituted β-hydroxy esters have been synthesized using fermenting cells of K. pneumoniae. A distinctive transformation-based strategy was adopted to access several carbocyclic and heterocyclic scaffolds. The synthesized scaffolds were further diversified by the use of stereoselective dihydroxylation to access cyclitols with glycosidase inhibitory activity.

    8. Asymmetric Cross-Aldol Reactions

      Synthesis of α,β-Unsaturated δ-Lactones by Vinyl Acetate Mediated Asymmetric Cross-Aldol Reaction of Acetaldehyde: Mechanistic Insights (pages 5247–5255)

      Manjeet Kumar, Arvind Kumar, Masood Rizvi, Manoj Mane, Kumar Vanka, Subhash C. Taneja and Bhahwal Ali Shah

      Article first published online: 15 JUL 2014 | DOI: 10.1002/ejoc.201402551

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      A tandem asymmetric cross-aldol reaction involving the in situ generation of acetaldehyde from vinyl acetate provides access to α,β-unsaturated δ-lactones as well as isochromenones with high enantioselectivities. DFT studies were performed to gain mechanistic insights into the reaction.

    9. Donor–Acceptor Systems

      Synthesis, Electrochemistry, Crystal Structures, and Optical Properties of Quinoline Derivatives with a 2,2′-Bithiophene Motif (pages 5256–5264)

      Aneta Slodek, Michal Filapek, Grazyna Szafraniec, Iwona Grudzka, Wojciech Andrzej Pisarski, Jan Grzegorz Malecki, Lidia Zur, Malgorzata Grela, Witold Danikiewicz and Stanislaw Krompiec

      Article first published online: 15 JUL 2014 | DOI: 10.1002/ejoc.201402241

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      Bithiophene-quinoline acceptor-donor materials have been prepared and their absorption and luminescence have been investigated. The quinolines are blue–green and orange–red emitters. The electrochemical, optical, and theoretical (DFT) characterization show the strong influence of the character of the substituent on the quinoline ring on their electrochemical and spectroscopic properties.

    10. Radical Alkylation

      Synthesis of Enantiomerically Pure (α-Phenylalkyl)amines with Substituents at the ortho Position through Diastereoselective Radical Alkylation Reaction of Sulfinimines (pages 5265–5272)

      José A. Fernández-Salas, M. Mercedes Rodríguez-Fernández, M. Carmen Maestro and José L. García-Ruano

      Article first published online: 11 JUL 2014 | DOI: 10.1002/ejoc.201402355

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      ortho-Substituted N-(tert-butylsulfinyl)benzaldimines are excellent acceptors in the intermolecular addition reactions of alkyl radicals. Easy removal of the sulfinyl group affords enantiopure α-branched amines. This short two-step sequence has been successfully applied to prepare ortho-hydroxy- and ortho-methoxybenzylamines, which are widely used as building blocks in chiral catalysis.

    11. Fluorinated Compounds

      One-Pot Preparation of Enantiopure Fluorinated β-Amino Acid Precursors (pages 5273–5280)

      Joshua H. Jones, Chandrakumar Appayee and Stacey E. Brenner-Moyer

      Article first published online: 15 JUL 2014 | DOI: 10.1002/ejoc.201402369

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      An organocascade reaction enabling the transformation of enals into α-fluoro- and α,α-difluoro-β-amino aldehydes in a single flask is described. This organocascade reaction combines carbon–nitrogen and carbon–fluorine bond-forming reactions. It is thus a new approach to fluorinated β-amino acid precursors, and generates products not accessible by existing one-pot methods.

    12. 1,4-Dihydropyridines

      Synthesis of 1,4-Dihydropyridines and Their Fluorescence Properties (pages 5281–5301)

      Shunsuke Sueki, Ryo Takei, Yuto Zaitsu, Junya Abe, Akane Fukuda, Keisuke Seto, Yukio Furukawa and Isao Shimizu

      Article first published online: 17 JUL 2014 | DOI: 10.1002/ejoc.201402426

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      The multicomponent coupling reactions of amine hydrochlorides, aldehydes, and acetals with various electron-withdrawing groups afford 2,6-unsubstituted 1,4-dihydropyridines (1,4-DHPs) in good yields and with high functional group tolerance. The fluorescence properties of the synthesized 1,4-DHPs have been evaluated.

    13. Total Synthesis

      Unsymmetrical vic-Tricarbonyl Compounds for the Total Syntheses of Cladoniamide G and Cladoniamide F (pages 5302–5311)

      Julia Schütte, Frank Kilgenstein, Michel Fischer and Ulrich Koert

      Article first published online: 17 JUL 2014 | DOI: 10.1002/ejoc.201402531

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      The enantioselective addition of indoles to mesoxalic ester amides has been investigated and the feasibility of these vic-tricarbonyl compounds as building blocks in natural product synthesis is shown in the syntheses of cladoniamide G and F. The synthesis involves arylation of a mesoxalic ester amide, a Suzuki cross-coupling to a 2,2′-biindole, and an intramolecular lactam formation as key steps.

    14. Hydrothiolation

      Efficient Synthesis of Isothiochromene Derivatives by Pd-Catalyzed Hydrothiolation Reaction (pages 5312–5317)

      Jie Feng, Meifang Lv, Guoping Lu and Chun Cai

      Article first published online: 15 JUL 2014 | DOI: 10.1002/ejoc.201402611

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      Isothiochromene could be efficiently synthesized by palladium-catalyzed intramolecular hydrothiolation. This protocol is free of foul-smelling thiols and enjoys excellent yields and excellent 6-endo-dig selectivities.

    15. Natural Products

      Synthesis and Cytotoxic Activity of a Small Naphthoquinone Library: First Synthesis of Juglonbutin (pages 5318–5330)

      Elke Brötz, Jennifer Herrmann, Jutta Wiese, Heidi Zinecker, Armin Maier, Gerhardt Kelter, Johannes F. Imhoff, Rolf Müller and Thomas Paululat

      Article first published online: 15 JUL 2014 | DOI: 10.1002/ejoc.201402272

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      A synthetic protocol has been designed to synthesize a small naphthoquinone library based around the natural products grecoketidone, hydroxylapachol, and juglonbutin. Biological profiling on some of the synthesized naphthoquinones revealed good activities against different tumor cell lines, with juglonbutin showing a remarkable activity against GSK3β with an IC50 value of 2 μM.

    16. Metathesis

      Modulation of Olefin Metathesis Reactions by Chelation (pages 5331–5345)

      Swetlana Scherbakow, Manfred Keller and Willi Bannwarth

      Article first published online: 15 JUL 2014 | DOI: 10.1002/ejoc.201402319

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      The hitherto unknown modulation of catalytic activity by adjacent chelating entities is demonstrated for ring-closing metathesis (RCM) as well as for cross metathesis (CM) reactions. For this purpose, a Hoveyda-type metathesis catalyst is modified by employing two different chelators. Their complexation led to an enhancement and adjustment of the catalytic activity.

    17. Coupling Reactions

      Copper(I)-Catalyzed Decarboxylative Coupling of Propiolic Acids with Secondary Amines and Aldehydes (pages 5346–5350)

      Denis S. Ermolat'ev, Huangdi Feng, Gonghua Song and Erik V. Van der Eycken

      Article first published online: 22 JUL 2014 | DOI: 10.1002/ejoc.201402338

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      A number of tertiary propargylamines was prepared by a copper(I)-catalyzed decarboxylative A3-coupling reaction of an alkynylcarboxylic acid with a secondary amine and an aldehyde. The procedure is also effective for 3-alkylpropiolic acids and for terminal propiolic acid.

    18. Chemoselective Alkylation

      Chemoselective Synthesis of N-Protected Alkoxyprolines under Specific Solvation Conditions (pages 5351–5355)

      Voichita Mihali, Francesca Foschi, Michele Penso and Gianluca Pozzi

      Article first published online: 15 JUL 2014 | DOI: 10.1002/ejoc.201402429

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      Several N-protected hydroxyprolines (trans-4-Hyp, cis-4-Hyp, trans-3-Hyp) were O-alkylated with activated, nonactivated, and polyfluorinated alkyl halides by using a THF/DMSO mixture as solvent. The reaction proceeds through the formation of the oxy-carboxy dianion and is completely chemoselective owing to specific solvation of the carboxyanion function.

    19. Chiral Ionic Liquids

      Chiral Room Temperature Ionic Liquids as Enantioselective Promoters for the Asymmetric Aldol Reaction (pages 5356–5363)

      Laura González, Jorge Escorihuela, Belén Altava, M. Isabel Burguete and Santiago V. Luis

      Article first published online: 17 JUL 2014 | DOI: 10.1002/ejoc.201402436

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      Chiral ionic liquids derived from natural amino acids are shown to be efficient solvents or additives for direct asymmetric aldol reactions. A match/mismatch effect between the configuration of the chiral ionic liquid and that of proline has been observed, with a higher enantioselectivity obtained for the (S)-proline/CIL 2 complex.

    20. Diastereoselective Arylation

      Boron/Zinc Exchange Reaction in the Diastereoselective Arylation of N-Protected L-Prolinal (pages 5364–5369)

      Bruna S. Martins and Diogo S. Lüdtke

      Article first published online: 15 JUL 2014 | DOI: 10.1002/ejoc.201402508

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      The boron/zinc exchange reaction has been used to generate aryl groups for use in a highly diastereoselective Felkin–Anh arylation of N-trityl-L-prolinal to give amino alcohols. A competing Cram-chelation pathway is prevented by the bulky trityl group at the pyrrolidine nitrogen atom. The amino alcohols possess structures that might be useful for the preparation of chiral ligands and catalysts.

    21. Aromaticity

      Aromaticity and Magnetic Properties of 1- and 2-Indenones and Their Aza Derivatives (pages 5370–5377)

      Jordi Poater, Miquel Solà, Ibon Alkorta and José Elguero

      Article first published online: 17 JUL 2014 | DOI: 10.1002/ejoc.201402509

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      1-Indenones are more stable than 2-indenones because they are more aromatic and have a more stabilizing π-component of the orbital interaction term. Tetrafluorination affects the 19F–19F spin-spin coupling constants of the 2-one series, but has no effect on the aromaticity.

  8. Correction

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Full Paper
    7. Short Communications
    8. Full Papers
    9. Correction
    1. You have free access to this content
      Total Synthesis of (+)-Antimycin A3b on Solid Supports (page 5378)

      Yusuke Iijima, Osamu Kimata, Santida Decharin, Hisashi Masui, Yoichiro Hirose and Takashi Takahashi

      Article first published online: 7 AUG 2014 | DOI: 10.1002/ejoc.201403036

      This article corrects:

      Total Synthesis of (+)-Antimycin A3b on Solid Supports

      Vol. 2014, Issue 22, 4725–4732, Article first published online: 3 JUN 2014

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