European Journal of Organic Chemistry

Cover image for Vol. 2012 Issue 14

May 2012

Volume 2012, Issue 14

Pages 2671–2855

  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
  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
    1. Graphical Abstract: Eur. J. Org. Chem. 14/2012 (pages 2671–2677)

      Article first published online: 2 MAY 2012 | DOI: 10.1002/ejoc.201290035

  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. C–C Bond Cleavage

      Transition-Metal-Mediated Cleavage and Activation of C–C Single Bonds (pages 2683–2706)

      Klaus Ruhland

      Article first published online: 23 FEB 2012 | DOI: 10.1002/ejoc.201101616

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      Four elemental reactions have to date been applied for the cleavage of C–C single bonds by transition metal complexes: (i) oxidative addition, (ii) β-carbon elimination, (iii) retro-allylation, (iv) migratorycarbonyl extrusion. These reactions, their mechanisms, their limitations and their potential are presented in this review along with (still rare) examples.

  5. Short Communications

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

      Photo- and Thermal-Induced Isomerization of Diels–Alder Adducts of Pentacene and TCNE (pages 2707–2710)

      Valentine K. Johns, Zheng Shi, Wenfang Hu, Jaime B. Johns, Shengli Zou and Yi Liao

      Article first published online: 30 MAR 2012 | DOI: 10.1002/ejoc.201200195

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      Isomerization of the second-ring Diels–Alder adduct to the central-ring adduct in the reaction of pentacene and tetracyanoethylene is reported. Photoisomerization can be induced in both directions, whereas thermal isomerization can be induced only from the second-ring adduct to the central-ring adduct.

    2. Domino Reactions

      Preparation of α-Sulfonylethanone Oximes from Oxidized Hydroxylamine (pages 2711–2714)

      Nan Liu, Ping Yin, Yue Chen, Yong Deng and Ling He

      Article first published online: 4 APR 2012 | DOI: 10.1002/ejoc.201200133

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      The addition to various olefins through a one-pot cascade oxidation–addition reaction to give sulfonylethanone oximes by using N-hydroxysulfonamides as a source of nitrogen and sulfur is reported. This method towards sulfonyl oximes proceeds in good yields with styrenes possessing either electron-donating or -withdrawing groups and constitutes an interesting functionalization of olefins.

    3. Acid/Base Catalysis

      Reversal of Anomeric Selectivity with O-Glycosyl Trichloroacetimidates as Glycosyl Donors and Thiols as Acceptors Under Acid/Base Catalysis (pages 2715–2719)

      Amit Kumar and Richard R. Schmidt

      Article first published online: 5 APR 2012 | DOI: 10.1002/ejoc.201200138

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      The reactions of O-α-glycosyl trichloroacetimidates and thiols with phenylboron difluoride as catalyst afford, without the support of anchimeric assistance, mainly β-thioglycosides. Clearly, the phenylboron difluoride–thiol adducts are responsible for this SN2-type reaction leading to a reversal of the anomeric configuration compared with standard glycosidation methods with thiols as acceptors.

    4. Asymmetric Synthesis

      A U-Turn in the Asymmetric Appel Reaction: Stereospecific Reduction of Diastereomerically Enriched Alkoxyphosphonium Salts Allows the Asymmetric Synthesis of P-Stereogenic Phosphanes and Phosphane Boranes (pages 2720–2723)

      Kamalraj V. Rajendran, Jaya S. Kudavalli, Katherine S. Dunne and Declan G. Gilheany

      Article first published online: 5 APR 2012 | DOI: 10.1002/ejoc.201200285

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      Enantioenriched P-stereogenic phosphanes or phosphane boranes were obtained in high yield by facile stereospecific reduction of diastereomeric alkoxyphosphonium salts (DAPS) formed by the dynamic resolution of phosphanes under Appel reaction conditions.

    5. Direct Aldol Reaction

      Direct Aldol Reaction of Pyruvic Derivatives: Catalytic Attempt To Synthesize Ulosonic Acids (pages 2724–2727)

      Osama El-Sepelgy, Darius Schwarzer, Piotr Oskwarek and Jacek Mlynarski

      Article first published online: 10 APR 2012 | DOI: 10.1002/ejoc.201200325

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      The catalytic direct aldol reaction of pyruvic aldehyde dimethyl acetal and 2-acetylthiazole with sugar aldehydes is demonstrated to be the key step in the synthesis of 3-deoxy-2-ulosonic acids.

  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. Chiral Resolution

      One-Pot Oxidation–Hydrocyanation Sequence Coupled to Lipase-Catalyzed Diastereoresolution in the Chemoenzymatic Synthesis of Sugar Cyanohydrin Esters (pages 2729–2737)

      Ari Hietanen and Liisa T. Kanerva

      Article first published online: 19 MAR 2012 | DOI: 10.1002/ejoc.201200086

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      A straightforward synthesis and kinetic resolution sequence is applied to protected methyl glycosides using lipases and nonenzymatic methods. Oxidation and hydrocyanation were combined in a one-pot procedure and the crude product was subjected to lipase-catalyzed acylation. The net effect is a stereoselective C–H substitution with a nitrile group at position 6 of the protected starting material.

    2. Intermolecular Interactions

      Synthesis and Solid-State Investigations of Oligo-Phenylene–Ethynylene Structures with Halide End-Groups (pages 2738–2747)

      Nicolas M. Jenny, Hong Wang, Markus Neuburger, Harald Fuchs, Lifeng Chi and Marcel Mayor

      Article first published online: 4 APR 2012 | DOI: 10.1002/ejoc.201200033

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      We have synthesized a series of halogen-end-capped oligo-phenylene-ethynylenes to study interactions at the solid/liquid interface and in crystal structures. Here we probe the interplay and diversity of intermolecular interactions between halide end-groups and oligo-phenylene-ethynylene backbones through solution depositions (2D) and X-ray crystal structures (3D). The STM images and crystal structures reveal a striking complementarity in each case.

    3. Blue Fluorescent Compounds

      Indenofluorene-Based Blue Fluorescent Compounds and Their Application in Highly Efficient Organic Light-Emitting Diodes (pages 2748–2755)

      Kum Hee Lee, Seul Ong Kim, Sunwoo Kang, Jin Yong Lee, Kyoung Soo Yook, Jun Yeob Lee and Seung Soo Yoon

      Article first published online: 10 APR 2012 | DOI: 10.1002/ejoc.201200117

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      A series of indenofluorene derivatives incorporating the (diphenylamino)arylvinyl group and di-tert-butylphenyl blocking units have been synthesized and their photophysical and electroluminescent properties examined. In the case of device 3C, the use of 3 as dopant in the emitting layer led to blue emission with an external quantum efficiency of 7.8 % at 20 mA cm–1.

    4. Push–Pull Chromophores

      1,1-Dicyano-4-[4-(diethylamino)phenyl]buta-1,3-dienes: Structure–Property Relationships (pages 2756–2765)

      Francesca Tancini, Yi-Lin Wu, W. Bernd Schweizer, Jean-Paul Gisselbrecht, Corinne Boudon, Peter D. Jarowski, Marten T. Beels, Ivan Biaggio and François Diederich

      Article first published online: 22 MAR 2012 | DOI: 10.1002/ejoc.201200111

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      Increasingly cyanated 1,1-dicyano-4-(N,N-diethylanilino)-substituted buta-1,3-dienes were synthesized by unusual routes and characterized by X-ray analyses. Their opto-electronic properties strongly depend on both the number and position of the additional CN groups. Substitution in positions 2 and 4 affects the intramolecular charge-transfer bands more strongly than substitution in position 3, which is rationalized by theoretical calculations.

    5. Heterocyclic Chemistry

      Intramolecular Iodine-Mediated Oxygen Transfer from Nitro Groups to C≡C Bonds (pages 2766–2773)

      Inga Cikotiene

      Article first published online: 27 MAR 2012 | DOI: 10.1002/ejoc.201200100

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      The first examples of highly regioselective iodine-mediated nitro-alkyne cycloisomerization to afford fused isoxazoles are presented.

    6. Organocatalysis

      Enantioselective β-Vinylation of α,β-Unsaturated Aldehydes Using a β-Nitroethyl Sulfone as Vinyl Anion Equivalent (pages 2774–2779)

      Chiara Gianelli, Rosa Lopez, Ángel Puente, Maitane Zalacain and Claudio Palomo

      Article first published online: 27 MAR 2012 | DOI: 10.1002/ejoc.201200150

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      A concise method for the asymmetric vinylation of enals is disclosed that employs β-nitroethyl phenyl sulfone as a new synthetic equivalent for the vinyl anion.

    7. Asymmetric Synthesis

      A C2-Symmetric Pool Based Flexible Strategy: An Enantioconvergent Synthesis of (+)-Valiolamine and (+)-Valienamine (pages 2780–2785)

      Hong-Jay Lo, Cheng-Yih Chen, Wei-Lin Zheng, Shang-Ming Yeh and Tu-Hsin Yan

      Article first published online: 30 MAR 2012 | DOI: 10.1002/ejoc.201101845

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      An enantioconvergent strategy was developed by using a C2-symmetric element within the chiral pool and by applying an iodine-promoted cyclization of an unsaturated carbonimidothioate for the regio- and diastereocontrolled installation of amino and hydroxy units. (+)-Valiolamine (1) and (+)-valienamine (2) were synthesized from commercially available D-tartaric acid by using this strategy.

    8. Calixarene Podands

      Synthesis of Calixarene-Based Bis(iminophosphoranes) and Their Use in Suzuki–Miyaura Cross-Coupling (pages 2786–2791)

      Laure Monnereau, David Sémeril and Dominique Matt

      Article first published online: 28 MAR 2012 | DOI: 10.1002/ejoc.201200082

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      Calix[4]arenes with two iminophosphorane units tethered at their upper rims have been synthesised for the first time and used in palladium-catalysed cross-couplings between phenylboronic acid and aryl halides. The good performances of the ligands possibly arise from their capacity to form chelate complexes in highly crowded metal environments.

    9. 1,4-Dipolar Cycloadditions

      A Three-Component Condensation for the Construction of the Spiro[indoline-3,3′-piperidin]-2-one Skeleton (pages 2792–2800)

      Hai-Bin Yang, Xiao-Yang Guan, Yin Wei and Min Shi

      Article first published online: 30 MAR 2012 | DOI: 10.1002/ejoc.201200185

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      1,4-Dipoles originating from reactions between pyridines and activated alkynes react with N-protected isatylidene derivatives to afford 1′,9a′-dihydrospiro[indoline-3,2-quinolizin]-2-one derivatives in excellent yields and with good diastereoselectivities. This new synthetic strategy is an efficient method for the construction of the spiro[indoline-3,3′-piperidin]-2-one skeleton.

    10. Modified DNA

      2,1,3-Benzothiadiazole-Modified DNA (pages 2801–2808)

      Florian Garo and Robert Häner

      Article first published online: 30 MAR 2012 | DOI: 10.1002/ejoc.201200231

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      Two different types of 2,1,3-benzothiadiazole (BTD) derivatives were introduced into DNA. Depending on the electronic properties of the BTD units, the DNA hybrids exhibit significantly different spectroscopic profiles. Fluorescence quenching by the individual nucleobases correlates with the respective oxidation potentials.

    11. Cooperative Catalysis

      Malononitrile-Assisted Highly Chemoselective Bismuth Triflate Catalyzed Conjugate Reduction of α,β-Unsaturated Ketones (pages 02809–2815)

      Jun-Yan Shang, Fei Li, Xing-Feng Bai, Jian-Xiong Jiang, Ke-Fang Yang, Guo-Qiao Lai and Li-Wen Xu

      Article first published online: 28 MAR 2012 | DOI: 10.1002/ejoc.201200020

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      A very simple, direct, bismuth-catalyzed 1,4-conjugate reduction protocol thatallows for the catalytic regioselective formation of substituted ketones from enones under mild conditions has been developed.

    12. Indole Alkaloids

      Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia (pages 2816–2823)

      Marion Girardot, Alice Gadea, Christiane Deregnaucourt, Alexandre Deville, Lionel Dubost, Bastien Nay, Alexandre Maciuk, Philippe Rasoanaivo and Lengo Mambu

      Article first published online: 10 APR 2012 | DOI: 10.1002/ejoc.201101738

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      Six new vobasinyl-iboga bisindole alkaloids and eight known compounds have been isolated from the stem bark ofMuntafara sessilifolia. Their structures were elucidated by NMR and MS and three of them were found to bear an unprecedented α-amino aldehyde group. The biosynthetic origin of these bisindoles is proposed. Their antiplasmodial and cytotoxic activities have been evaluated.

    13. Strained Molecules

      Generation and Chemistry of Tricyclo[3.2.1.02,4]oct-2(3)-ene (pages 2824–2830)

      Gon-Ann Lee, Lien-En Chan, Ru-Ting Tsai and Ko-Chou Chen

      Article first published online: 5 APR 2012 | DOI: 10.1002/ejoc.201200048

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      The highly strained 1,3-fused polycyclic cyclopropene 25 favors the ring-opened vinylcarbene form, which undergoes a number of reactions including addition of water, insertion into the C–H bond α to the oxygen atom in THF to yield exo products, and [1+2] addition to the C=C bond in furan, preferentially forming the endo adduct. Furthermore, on heating, the addition products 27 and 28 rearrange to aldehyde 29.

    14. Tetraalkynylarenes

      Regioselective Synthesis of Tetraalkynylarenes by Consecutive Dual Sonogashira Coupling Reactions of the Bis(triflate) of 4,5-Diiodobenzene-1,2-diol (pages 2831–2836)

      Thomas J. Fisher and Patrick H. Dussault

      Article first published online: 27 MAR 2012 | DOI: 10.1002/ejoc.201200079

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      The bis(triflate) ester of 4,5-diiodobenzene-1,2-diol provides a useful synthon for the preparation of unsymmetrical tetraalkynylarenes.

    15. Profragrances

      Preparation of Imidazolidin-4-ones and Their Evaluation as Hydrolytically Cleavable Precursors for the Slow Release of Bioactive Volatile Carbonyl Derivatives (pages 2837–2854)

      Alain Trachsel, Barbara Buchs, Guillaume Godin, Aurélien Crochet, Katharina M. Fromm and Andreas Herrmann

      Article first published online: 22 MAR 2012 | DOI: 10.1002/ejoc.201200081

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      1,3-Heterocycles have repeatedly been considered as hydrolytically cleavable precursors for the release of fragrant aldehydes or ketones. Dynamic headspace analysis above a cotton surface showed that glycinamide-based imidazolidinones represent in practical applications a good compromise between precursor stability and release efficiency.

  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
      Lewis Acid Catalysed [4+2] Heterocycloadditions between Ketone Enol Ethers and β-Ethylenic α-Oxo Esters (page 2855)

      Arnaud Martel, Stéphane Leconte, Gilles Dujardin, Eric Brown, Vincent Maisonneuve and Richard Retoux

      Article first published online: 30 MAR 2012 | DOI: 10.1002/ejoc.201200157

      This article corrects:

      Lewis Acid Catalysed [4+2] Heterocycloadditions between Ketone Enol Ethers and β-Ethylenic α-Oxo Esters

      Vol. 2002, Issue 3, 514–525, Article first published online: 14 JAN 2002

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