European Journal of Organic Chemistry

Cover image for Vol. 2013 Issue 21

July 2013

Volume 2013, Issue 21

Pages 4455–4680

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. You have free access to this content
      Total Synthesis of the Hypermodified tRNA Nucleoside Epoxyqueuosine (Eur. J. Org. Chem. 21/2013)

      Ines Thoma and Thomas Carell

      Article first published online: 10 JUL 2013 | DOI: 10.1002/ejoc.201390058

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      The cover picture shows the structures of several 7-deazaguanosine (Q, galQ, preQ1, preQ0, gluQ, oQ) and the X-ray structure of tRNAAsp.The tRNA data was obtained from the pbd file of the strcuture published by Briand et al. (J. Mol. Biol. 2000, 299, 1051) containing the hypermodified nucleoside queuosine (Q) in the wobble position (position 34) and the image was created in PyMOL. Prokaryotes can synthesize Q de novo via epoxyqueuosine (oQ) as the direct biosynthesis precursor. The total synthesis of oQ discussed in the Short Communication by I. Thoma and T. Carell on page 4483 ff..

  2. Graphical Abstract

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

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

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

      You have full text access to this OnlineOpen article
      Towards Tartaric-Acid-Derived Asymmetric Organocatalysts (pages 4471–4482)

      Katharina Gratzer, Guddeangadi N. Gururaja and Mario Waser

      Article first published online: 3 JUN 2013 | DOI: 10.1002/ejoc.201201675

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      Tartaric acid is one of the most prominent naturally occurring chiral compounds. Whereas its application in the production of chiral ligands for metal-catalysed reactions has been exhaustively investigated, its potential to provide new organocatalysts has been less extensively explored. Nevertheless, some impressive results have been published over the last decade, and are the topic of this review.

  5. Short Communications

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

      Total Synthesis of the Hypermodified tRNA Nucleoside Epoxyqueuosine (pages 4483–4485)

      Ines Thoma and Thomas Carell

      Article first published online: 7 JUN 2013 | DOI: 10.1002/ejoc.201300586

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      The structure of the hypermodified nucleoside epoxyqueuosine (oQ), which is the biosynthetic precursor of queuosine (Q), was confirmed by total synthesis and HPLC–MS analysis of natural samples.

    2. Monofluoroalkenes

      One-Step Stereoselective Synthesis of Trisubstituted Monofluoroalkenes from 3,3,3-Trifluoropropionates (pages 4486–4489)

      Mercedes Lecea, Adrien Grassin, Leticia Ferreiro-Mederos, Sabine Choppin, Antonio Urbano, M. Carmen Carreňo and Françoise Colobert

      Article first published online: 13 JUN 2013 | DOI: 10.1002/ejoc.201300551

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      (E)-Monofluoroalkenes were obtained in good yields and stereoelectivities by condensation of organolithium or Grignard reagents to methyl or benzyl 3,3,3-trifluoropropionate.

    3. Bifunctional Organocatalysts

      Tether-Free Immobilized Bifunctional Squaramide Organocatalysts for Batch and Flow Reactions (pages 4490–4494)

      György Kardos and Tibor Soós

      Article first published online: 17 JUN 2013 | DOI: 10.1002/ejoc.201300626

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      Easily accessible, robust, and cheap immobilized organocatalysts are developed and used to prepare Michael adducts in excellent yields with excellent enantioselectivities, even on the gram scale.

    4. Asymmetric Thiolysis

      Highly Enantioselective Thiolysis of Prochiral Cyclic Anhydrides Catalyzed by Amino Alcohol Bifunctional Organocatalysts and Its Application to the Synthesis of Pregabalin (pages 4495–4498)

      Hong-Jun Yang, Fang-Jun Xiong, Xiao-Fei Chen and Fen-Er Chen

      Article first published online: 17 JUN 2013 | DOI: 10.1002/ejoc.201300464

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      A highly enantioselective thiolysis of prochiral cyclic anhydrides was achieved with chiral sulfonamide bifunctional organocatalysts based on an amino alcohol scaffold. The usefulness of this methodology was demonstrated through a synthetic application to pregabalin.

    5. Domino Reactions

      Amine-Catalyzed Cascade Synthesis of 3,4-Diunsubstituted Coumarins (pages 4499–4502)

      Jia Wei, Pengcheng Wang, Qianfa Jia, Jiaoyao Huang, Zhiyun Du, Kun Zhang and Jian Wang

      Article first published online: 12 JUN 2013 | DOI: 10.1002/ejoc.201300538

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      We disclose an efficient route to synthesize 3,4-diunsubstituted coumarins through a cascade organocatalytic reaction. The reaction is catalyzed by using of a combination of benzylamine (10 mol-%) and triethylamine (10 mol-%). Various salicylaldehydes are tested, and the corresponding coumarin products are obtained in good to high yields under mild and metal-free reaction conditions.

    6. Oxidation

      Solvent-Controlled Copper-Catalyzed Oxidation of Benzylic Alcohols to Aldehydes and Esters (pages 4503–4508)

      Yefeng Zhu and Yunyang Wei

      Article first published online: 12 JUN 2013 | DOI: 10.1002/ejoc.201300668

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      Depend on solvent! Under solvent-free conditions, Cu-catalyzed oxidative self-esterification and cross-esterification of benzylic alcohols with various aliphatic alcohols proceed smoothly to give the corresponding esters in good yields. If DMF is used as a solvent, the benzylic alcohols are selectively converted into the corresponding aldehydes in excellent yields. DTBP = di-tert-butyl peroxide.

    7. Flow Chemistry

      Fluorenylmethoxycarbonyl-N-methylamino Acids Synthesized in a Flow Tube-in-Tube Reactor with a Liquid–Liquid Semipermeable Membrane (pages 4509–4513)

      Annette E. Buba, Stefan Koch, Horst Kunz and Holger Löwe

      Article first published online: 17 JUN 2013 | DOI: 10.1002/ejoc.201300705

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      In a continuous flow tube-in-tube reactor containing a liquid–liquid transfer semipermeable membrane, reductive ring opening of N-Fmoc-oxazolidinones efficiently affords Fmoc-N-methylamino acid building blocks. Fmoc = 9-fluorenylmethoxycarbonyl, TFA = trifluoroacetic acid.

  6. Full Papers

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

      A Flexible Strategy Towards Thienyl-, Oxazolyl- and Pyridyl-Fused Fluorenones (pages 4515–4522)

      Amel Souibgui, Anne Gaucher, Jérôme Marrot, Faouzi Aloui, Florence Mahuteau-Betzer, Bechir Ben Hassine and Damien Prim

      Article first published online: 12 JUN 2013 | DOI: 10.1002/ejoc.201300233

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      Thienyl-, oxazolyl- and pyridyl-fused benzo[c]fluorenones were prepared from bromotetralone according to a flexible and short step strategy. The photophysical properties of the products depend on the nature of the fused heterocycle and are crucially influenced by structural modulations.

    2. Chiral Cyclophanes

      Synthesis, Chiral Resolution, and Absolute Configuration of Dissymmetric 4,12-Difunctionalized [2.2]Paracyclophanes (pages 4523–4532)

      Georg Meyer-Eppler, Elisabeth Vogelsang, Christian Benkhäuser, Andreas Schneider, Gregor Schnakenburg and Arne Lützen

      Article first published online: 7 JUN 2013 | DOI: 10.1002/ejoc.201300412

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      Dissymmetric 4,12-difunctionalized [2.2]paracyclophane derivatives were prepared and resolved on a semipreparative scale either by conventional or recycling HPLC with a chiral stationary phase. The absolute configurations of the resolved enantiomers were assigned by X-ray diffraction and/or comparison of specific optical rotations with literature data.

    3. Donor-Acceptor Systems

      Synthesis of Specific Solvatochromic D-π-A Dyes with Pyridinium Ring as Electron-Withdrawing Group for Dye-Sensitized Solar Cells (pages 4533–4538)

      Yousuke Ooyama, Yuichiro Oda, Tomonobu Mizumo, Yutaka Harima and Joji Ohshita

      Article first published online: 12 JUN 2013 | DOI: 10.1002/ejoc.201300465

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      Specific solvatochromic D-π-A dyes with a pyridinium ring as electron-withdrawing group, which can lead to a large bathochromic shift of absorption band in halogenated solvents, have been developed and applied as a photosensitizers to dye-sensitized solar cells.

    4. Strained Molecules

      Rearrangements of Furan-, Thiophene- and N-Boc-Pyrrole-Derived Donor-Acceptor Cyclopropanes: Scope and Limitations (pages 4539–4551)

      Johannes Kaschel, Tobias F. Schneider, Patrick Schirmer, Christian Maaß, Dietmar Stalke and Daniel B. Werz

      Article first published online: 7 JUN 2013 | DOI: 10.1002/ejoc.201300390

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      Brønsted acid catalyzed ring-enlargement and ring-opening reactions of donor-acceptor cyclopropanes with ketones as accepting unit and oxygen, sulfur and nitrogen as electron-donating moiety have been investigated. The mode of intramolecular rearrangement of the carbonyl-substituted cyclopropanes depends on subtle differences in the substitution pattern of the cyclopropane.

    5. Oxidative Cyclisation

      Access to Di- and Trisubstituted Oxazoles by NBS-Mediated Oxidative Cyclisation of N-Acyl Amino Acid Derivatives (pages 4552–4557)

      Surendar Reddy Bathula, Muktapuram Prathap Reddy, K. K. Durga Rao Viswanadham, Pochampalli Sathyanarayana and Maddi Sridhar Reddy

      Article first published online: 12 JUN 2013 | DOI: 10.1002/ejoc.201300421

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      A highly convenient synthesis of various di- and trisubstituted functionalized oxazoles is described in a metal- and catalyst-free NBS-mediated oxidative cyclisation of N-acylated amino acid derivatives.

    6. Natural Product Synthesis

      Total Synthesis of (+)-Strongylin A, a Rearranged Sesquiterpenoid Hydroquinone from a Marine Sponge (pages 4558–4563)

      Takaaki Kamishima, Takuya Kikuchi and Tadashi Katoh

      Article first published online: 13 JUN 2013 | DOI: 10.1002/ejoc.201300438

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      (+)-Strongylin A has been synthesized for the first time by starting from (+)-5-methyl-Wieland–Miescher ketone (16 % overall yield in 14 steps). The characteristic tetracyclic core structure was constructed in a domino dehydroxylation/rearrangement/cyclization reaction.

    7. Sequential Catalysis

      One-Pot Synthesis of Camalexins and 3,3′-Biindoles by the Masuda Borylation–Suzuki Arylation (MBSA) Sequence (pages 4564–4569)

      Boris O. A. Tasch, Dragutin Antovic, Eugen Merkul and Thomas J. J. Müller

      Article first published online: 19 MAR 2013 | DOI: 10.1002/ejoc.201300133

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      The Masuda borylation/Suzuki arylation sequence furnishes in a concise one-pot manner camalexins and 3,3′-biindoles, compounds that show pronounced antifungal, antimicrobial, and cytotoxic activities.

    8. C–H Activation

      Cu(OTf)2-Catalyzed Dehydrogenative C–H Activation under Atmospheric Oxygen: An Expedient Approach to Pyrrolo[3,2-d]pyrimidine Derivatives (pages 4570–4577)

      B. Roy, Somjit Hazra, Biplab Mondal and K. C. Majumdar

      Article first published online: 5 JUN 2013 | DOI: 10.1002/ejoc.201300275

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      A new approach to pyrrolo[3,2-d]pyrimidine derivatives was accomplished through a dehydrogenative C–H activation of uracil in the open atmosphere with Cu(OTf)2 as a catalyst. This method features mild reaction conditions and operational simplicity. The use of K2CO3 as a base significantly improves the yield of the reaction.

    9. Heterocyclic Chemistry

      Synthesis of Substituted Oxazoles from N-Benzyl Propargyl Amines and Acid Chlorides (pages 4578–4585)

      Henrik v. Wachenfeldt, Filip Paulsen, Anders Sundin and Daniel Strand

      Article first published online: 6 JUN 2013 | DOI: 10.1002/ejoc.201300285

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      The reaction between N-benzylpropargylamines and acid chlorides at elevated temperatures gives oxazoles in up to 99 % yield. Twenty-one examples are demonstrated varying the substitution at all positions of the heterocycle.

    10. Total Synthesis

      Total Synthesis of Umuravumbolide and Hyptolide Through Silicon-Tethered Ring-Closing Metathesis (pages 4586–4593)

      Partha Sarathi Chowdhury and Pradeep Kumar

      Article first published online: 12 JUN 2013 | DOI: 10.1002/ejoc.201300302

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      An efficient total synthesis of umuravumbolide and hyptolide has been achieved by using temporary silicon-tethered ring-closing metathesis. The stereogenic centres were generated by using asymmetric allyl boration and proline-catalysed α-aminoxylation with high degrees of enantioselectivity.

    11. Medicinal Chemistry

      Theophyllinylpyrimidine Scaffolds Undergo Intramolecular Cyclization Reactions to Form 1,3-Diazepines and Imidazopurines (pages 4594–4606)

      Iryna O. Lebedyeva, V'yacheslav M. Povstyanoy, Aleksey B. Ryabitskii, Oleksandr Panasyuk, Evgen Ivahnenko, Vera P. Lozova, Igor Markevich, Svitlana Allakhverdova and Mykhaylo V. Povstyanoy

      Article first published online: 12 JUN 2013 | DOI: 10.1002/ejoc.201300360

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      Polyheterocyclic pyrimidinyltheophyllines have been synthesized from pyrimidine and theophylline precursors. Attempts to cyclize these reactive bis-heterocyclic systems resulted in the formation of the diazepine moiety. Modification of the reaction conditions led to the formation of imidazo[2,1-f]purines.

    12. Heterocyclic Chemistry

      Three-Component Synthesis of Indanone-Fused Spirooxindole Derivatives (pages 4607–4613)

      Xue-Bing Chen, Xi-Ming Liu, Rong Huang, Sheng-Jiao Yan and Jun Lin

      Article first published online: 10 JUN 2013 | DOI: 10.1002/ejoc.201300376

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      A simple, straightforward and versatile multicomponent protocol for the synthesis of indanone-fused spirooxindole derivatives has been developed. The strategy involves the one-pot three-component reaction of heterocyclic ketene aminals, 1H-indene-1,3(2H)-dione and the dicarbonyl compounds isatins or acenaphthenequinone in an ethanol/water medium catalysed by p-TSA at reflux.

    13. Heterocalixarenes

      Calix[2]triazole[2]arenes; A Class of Hybrid Heterocalixarenes (pages 4614–4623)

      Jihee Cho, Seokwoo Lee, Soonho Hwang, Sang Hoon Kim, Jong Seung Kim and Sanghee Kim

      Article first published online: 5 JUN 2013 | DOI: 10.1002/ejoc.201300401

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      A series of calix[2]triazole[2]arenes, members of the heterocalixarene family, were synthesized and their various conformational structures were characterized on the basis of their X-ray crystal structures and NMR spectra.

    14. Asymmetric Catalysis

      Highly Efficient Asymmetric Conjugate Hydrocyanation of Aromatic Enones by an Anionic Chiral Phosphate Catalyst (pages 4624–4633)

      Yao-Feng Wang, Wei Zeng, Muhammad Sohail, Jiyi Guo, Shaoxiang Wu and Fu-Xue Chen

      Article first published online: 5 JUN 2013 | DOI: 10.1002/ejoc.201300406

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      The asymmetric conjugate hydrocyanation of poorly reactive chalcone-type enones with benzophenone cyanohydrin using an anionic chiral phosphate catalyst has been achieved in high yields (72–96 %) and excellent enantioselectivities (92–98 % ee). It is proposed that the chiral anion modifies HCN, the real nucleophile, in the transition state through hydrogen bonding.

    15. Intramolecular Wittig Reactions

      Facile Synthesis of Functional Tricyclic Fused Furans by Intramolecular Wittig Reactions (pages 4634–4641)

      Yi-Ling Tsai, Utpal Das, Siang-en Syu, Chia-Jui Lee and Wenwei Lin

      Article first published online: 10 JUN 2013 | DOI: 10.1002/ejoc.201300426

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      Functionalized fused furan derivatives were prepared in an intramolecular Wittig reaction in one step starting from simple and readily available substrates. The reaction is belived to proceed via an ylide intermediate. Furthermore, the products could be easily transformed into synthetically useful naphthofurans.

    16. Tuberculosis

      Total Synthesis of the Phenolic Glycolipid Mycoside B and the Glycosylated p-Hydroxybenzoic Acid Methyl Ester HBAD-I, Virulence Markers of Mycobacterium tuberculosis (pages 4642–4654)

      Santiago Barroso, Danny Geerdink, Bjorn ter Horst, Eva Casas-Arce and Adriaan J. Minnaard

      Article first published online: 12 JUN 2013 | DOI: 10.1002/ejoc.201300437

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      The phenolic glycolipid mycoside B and the related phenolic glycoside HBAD-I from Mycobacterium tuberculosis have been synthesized for the first time. A highly convergent strategy was used featuring catalytic asymmetric 1,4-additions of MeMgBr and Me2Zn and a late-stage Sonogashira coupling as the key steps.

    17. Antiviral Agents

      From Cyclopentadiene to Isoxazoline-Carbocyclic Nucleosides; Synthesis of Highly Active Inhibitors of Influenza A Virus H1N1 (pages 4655–4665)

      Paolo Quadrelli, Mariella Mella, Laura Legnani and Dalya Al-Saad

      Article first published online: 13 JUN 2013 | DOI: 10.1002/ejoc.201300119

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      The synthesis of nornucleosides incorporating a quinoline moiety was tuned through the application of nitrosocarbonyl group chemistry. The synthesis hinges on exo-selective 1,3-dipolar cycloaddition of quinolinenitrile oxide to 2,3-oxazanorborn-5-enes and elaboration of the cycloadducts. The nucleosides were tested as inhibitors of a variety of viruses and some were found highly active against Flu A H1N1.

    18. Medicinal Chemistry

      Regioselective 2-Imino-1,3-thiazolidine vs. 2-Imino-1,3-oxazolidine Formation from the Vicinal sec-Amino Alcohol of Desosamine (pages 4666–4673)

      Zorica Marušić Ištuk, Ines Vujasinovi, Ana Čikoš and Goran Kragol

      Article first published online: 7 JUN 2013 | DOI: 10.1002/ejoc.201300266

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      A regioselective and mild one-pot method based on the Mukaiyama reagent-induced cyclization of vicinal sec-amino alcohols of desosamine origin to N′-alkyl-2-imino-1,3-thiazolidines was developed. The inversion of configuration at the carbon bearing the hydroxy group was unambiguously established using NMR-based conformational analysis. The reaction mechanism was proposed.

    19. Magnetic Nanoparticles

      Magnetically Recoverable CuFe2O4 Nanoparticles: Catalyzed Synthesis of Aryl Azides and 1,4-Diaryl-1,2,3-triazoles from Boronic Acids in Water (pages 4674–4680)

      A. Suresh Kumar, M. Amarnath Reddy, M. Knorn, O. Reiser and B. Sreedhar

      Article first published online: 5 JUN 2013 | DOI: 10.1002/ejoc.201300343

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      Magnetic and catalytically competent CuFe2O4 nanoparticles proved to be highly efficient in the three-component synthesis of 1,4-diaryl-1,2,3-triazoles, a class of compounds that has been recognized for its anticancer activity.

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