European Journal of Organic Chemistry

Cover image for Vol. 2009 Issue 8

March 2009

Volume 2009, Issue 8

Pages 1099–1274

  1. Cover Picture

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

      Transition-Metal-Catalyzed Hydroarylation Reactions of Alkynes Through Direct Functionalization of C–H Bonds: A Convenient Tool for Organic Synthesis (pages 1111–1125)

      Tsugio Kitamura

      Version of Record online: 8 JAN 2009 | DOI: 10.1002/ejoc.200801054

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      Hydroarylation of alkynes is an efficient and atom-economic process that directly introduces alkenyl moieties into aromatic substrates. This microreview focuses on hydroarylation catalyzed by transition metals through direct functionalization of C–H bonds, affording aromatic alkenes, diaryl-alkanes, heterocycles, carbocycles, and arylbutadienes.

  5. Short Communications

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

      Low-Barrier Pathway for endo-Cleavage Induced Anomerization of Pyranosides with N-Benzyl-2,3-trans-oxazolidinone Groups (pages 1127–1131)

      Hiroko Satoh, Jürg Hutter, Hans Peter Lüthi, Shino Manabe, Kazuyuki Ishii and Yukishige Ito

      Version of Record online: 29 JAN 2009 | DOI: 10.1002/ejoc.200801140

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      endo-Cleavage induced anomerization reactions were experimentally (by reduction reactions) and theoretically investigated. BLYP/6-31G(d,p) calculations showed that for pyranosides with 2,3-trans-oxazolidinones, BF3 induces endo-cleavage followed by rotation of the C1–C2 bond to give the α form via lower-energy transition states.

    2. Ytterbium Triflate Catalysis

      Preparation of Triaryl- and Triheteroarylmethanes under Ytterbium Triflate Catalysis and Solvent-Free Conditions (pages 1132–1135)

      Salvatore Genovese, Francesco Epifano, Caroline Pelucchini and Massimo Curini

      Version of Record online: 29 JAN 2009 | DOI: 10.1002/ejoc.200801115

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      Ytterbium triflate was shown to be an effective catalyst in promoting the synthesis of triaryl- and triheteroarylmethanes fromdifferently substituted aldehydes and 2-methylfuran or methoxybenzene, respectively.

    3. Natural Product Synthesis

      A Concise Synthesis of R-(–)-Cicutoxin, a Natural 17-Carbon Polyenyne (pages 1136–1138)

      Benjamin W. Gung and Ann O. Omollo

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/ejoc.200801172

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      A concise synthesis of the natural polyenyne R-(–)-cicutoxin (1) is described. After several trials, the successful synthesis commenced with three key fragments, R-(–)1-hexyn-3-ol (8), 1,4-diiodo-1,3-butadiene (9), and THP-protected 4,6-heptadiyn-1-ol (6). The triply convergent synthesis gave R-(–)-cicutoxin in 18 % overall yield.

    4. Marine Metabolites

      A Convenient Enantiospecific Route towards Bioactive Merosesquiterpenes by Cationic-Resin-Promoted Friedel–Crafts Alkylation with α,β-Enones (pages 1139–1143)

      Enrique Alvarez-Manzaneda, Rachid Chahboun, Eduardo Cabrera, Esteban Alvarez, Ali Haidour, Jose Miguel Ramos, Ramón Alvarez-Manzaneda, Rubén Tapia, Hakima Es-Samti, Antonio Fernández and Inmaculada Barranco

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/ejoc.200801174

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      A new methodology for synthesizing bioactive merosesquiterpenes, such as the marine (+)-puupehenone and related metabolites, is reported. The sequence involves a cationic-resin-promoted Friedel–Crafts alkylation of an aryl ether with a norsesquiterpene α,β-enone and further C–O coupling catalyzed by palladium.

    5. Iron Catalysis

      Iron-Catalyzed One-Pot Oxidative Esterification of Aldehydes (pages 1144–1147)

      Xiao-Feng Wu and Christophe Darcel

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/ejoc.200801176

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      A highly efficient, mild, and simple protocol for the direct oxidative esterificationof aromatic and aliphatic aldehydes withsimple alcohols was accomplished by using a catalytic amount of Fe(ClO4)3·xH2O with hydroperoxide as an oxidant.

    6. Iminium Ion Generator

      B(OMe)3 as a Nonacidic Iminium Ion Generator in Mannich- and Ugi-Type Reactions (pages 1148–1151)

      Yusuke Tanaka, Kousuke Hidaka, Tomoaki Hasui and Michinori Suginome

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/ejoc.200801190

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      Trimethoxyborane serves as an inexpensive and virtually nonacidic iminium ion generator, allowing Mannich-type reaction of aldehydes, secondary amines, and ketene silyl acetals to afford β-amino esters. The reagent also allowed nonacidic Ugi-type three-component coupling of aldehydes, secondary amines, and isocyanides, which leads to the formation of α-amino acid derivatives.

  6. Full Papers

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

      Screening the Structural Space of Bicyclo-DNA: Synthesis and Thermal Melting Properties of bc4,3-DNA (pages 1153–1162)

      Andrea Stauffiger and Christian J. Leumann

      Version of Record online: 18 DEC 2008 | DOI: 10.1002/ejoc.200801034

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      A novel member of the bicyclonucleoside family [4.3.0]bicyclothymidine was synthesized and incorporated into oligodeoxynucleotides. Their pairing properties to complementary DNA and RNA were investigated and found to be similar to that of the known [3.3.0]bicyclo-DNA.

    2. Supramolecular Device

      Selective Positioning of CB[8] on Two Linked Viologens and Electrochemically Driven Movement of the Host Molecule (pages 1163–1172)

      Samir Andersson, Dapeng Zou, Rong Zhang, Shiguo Sun, Björn Åkermark and Licheng Sun

      Version of Record online: 29 JAN 2009 | DOI: 10.1002/ejoc.200801012

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      The host CB[8] was selectively positioned on the DMV moiety of a DMV-MV molecular dyad and subsequently moved to the MV moiety through an electrochemical reduction. The host was moved back to theDMV moiety by oxidation. The ability to reversible move the host from one guest to another contributes to the fundamental understanding required for the design of more advanced molecular devices.

    3. Pd-Catalyzed Carbonylation

      Synthesis of Phenanthro[9,10-b]indolizidin-9-ones, Phenanthro[9,10-b]quinolizidin-9-one, and Related Benzolactams by Pd(OAc)2-Catalyzed Direct Aromatic Carbonylation (pages 1173–1180)

      Satoshi Yamashita, Nobuhito Kurono, Hisanori Senboku, Masao Tokuda and Kazuhiko Orito

      Version of Record online: 22 JAN 2009 | DOI: 10.1002/ejoc.200801047

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      Phenanthro[9,10-b]indolizidin-9-ones, phenanthro[9,10-b]quinolizidin-9-one, and related benzolactams were obtained by phosphane-free Pd(OAc)2-catalyzed direct aromatic carbonylation from the corresponding amines. This constitutes a formal synthesis of the representative phenanthroindolizidine and -quinolizidine alkaloids (±)-tylophorine, (±)-antofine, and (±)-cryptopleurine.

    4. Thermal Rearrangements

      Thermal Rearrangements of Perchlorohexatrienes–Structures and Experimental and Theoretical Evaluation of Pathways to Isomerization and Cyclization (pages 1181–1190)

      Heiner Detert, Dieter Lenoir and Hendrik Zipse

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/ejoc.200801076

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      Ab initio calculations and pyrolysis experiments are combined to investigate theunique chemical behavior of perchloroalkenes. Thermolysis of perchlorohexatrienes in the condensed and in the gas phase result in cis/trans isomerisation followed by cyclization to cyclopentene or hexachlorobenzene.

    5. Asymmetric Hydroformylation

      C1-Symmetric Diphosphite Ligands Derived from Carbohydrates: Influence of Structural Modifications on the Rhodium-Catalyzed Asymmetric Hydroformylation of Styrene (pages 1191–1201)

      Aitor Gual, Cyril Godard, Carmen Claver and Sergio Castillón

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/ejoc.200801093

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      New diphosphite ligands derived from1,2:5,6-di-O-isopropylideneglucofuranosehave been synthesized and successfully tested in the rhodium-catalyzed asymmetric hydroformylation of styrene. The modification of the carbohydrate backbone and diphosphite bridge affects the activity and selectivity of the reaction.

    6. Reactivity

      Nucleophilic Reactivities of Azulene and Fulvenes (pages 1202–1206)

      Mariusz Kędziorek, Peter Mayer and Herbert Mayr

      Version of Record online: 16 JAN 2009 | DOI: 10.1002/ejoc.200801099

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      The kinetics of the reactions of benzhydrylium ions with azulene and a series of fulvenes were determined and analyzed according to the correlation log k(20 °C) = s(N + E). The nucleophilicities (N) of thetitle compounds allowed for the comparison of their reactivities with those of other π-systems and will guide synthetic chemists to explore further electrophilic reaction partners.

    7. Double H-Bond Activation

      DFT Studies on Double Hydrogen Bond Catalysis of Reactions of Distinct Polarity (pages 1207–1213)

      Enrique Gómez-Bengoa

      Version of Record online: 20 JAN 2009 | DOI: 10.1002/ejoc.200801102

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      The bifurcated and cooperative complexation of carbonyls with double-site hydrogen-bond donors were computationally studied. A different activation pattern wasfound for reactions of distinct polarity, like the Diels–Alder and enamine-aldol reactions.

    8. Brønsted Heterogeneous Catalysis

      Direct Aza-Diels–Alder Reaction in Water Catalyzed by Layered α-Zirconium Hydrogen Phosphate and Sodium Dodecyl Sulfate (pages 1214–1220)

      Umberto Costantino, Francesco Fringuelli, Mara Orrù, Morena Nocchetti, Oriana Piermatti and Ferdinando Pizzo

      Version of Record online: 21 JAN 2009 | DOI: 10.1002/ejoc.200801132

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      The direct aza-Diels–Alder reaction between 2-cyclohexen-1-one and benzaldimines in water has been efficaciously catalyzed by layered α-zirconium hydrogen phosphate (α-ZrP) in the presence of sodium dodecyl sulfate . The one-pot, three-component version of the reaction andthe recycling of both the catalyst and the aqueous mother liquor in toto have also been investigated.

    9. Cross Couplings

      Molybdenum-Catalyzed α-Hydrostannations of Propargylamines as the Key Step in the Synthesis of N-Heterocycles (pages 1221–1227)

      Hechun Lin and Uli Kazmaier

      Version of Record online: 13 JAN 2009 | DOI: 10.1002/ejoc.200801157

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      The Mo-catalyzed hydrostannation of propargylic amines and amides gave rise to functionalized vinylstannanes in goodyield. Starting from halogenated aromaticamines, indoles and isoquinolines wereaccessible through intramolecular Stille couplings.

    10. Superelectrophilic Cyclizations

      Cyclization Reactions of 1-Amino-5-trifluoromethyl-5-thienyl-1-azapenta-1,4-dien-3-ones under Superelectrophilic Conditions: Synthesis of Novel Benzothiophenols, Cyclopentenols and Dihydrodiazepinols (pages 1228–1240)

      Nugzar Ghavtadze, Roland Fröhlich and Ernst-Ulrich Würthwein

      Version of Record online: 22 JAN 2009 | DOI: 10.1002/ejoc.200801194

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      CF3-substituted 1-amino-5-thienyl-1-aza-1,4-dien-3-ones 5 undergo three different cyclization reactions upon treatment with an excess of triflic acid, leading to novel five-, six- and seven-membered carbo- and heterocycles depending on the substitution pattern. The cyclization reactions are believed to proceed under superelectrophilic conditions involving mono- and dicationic intermediates.

    11. Push–Pull Proton Sponges

      1,8-Bis(dialkylamino)-4,5-dinitronaphthalenes and 4,5-Bis(dimethylamino)naphthalene-1,8-dicarbaldehyde as “Push–Pull” Proton Sponges: When and Why Formyl Groups Become Stronger π-Electron Acceptors than Nitro Groups (pages 1241–1248)

      Valery A. Ozeryanskii, Alexander F. Pozharskii, Alexander K. Artaryan, Nikolai V. Vistorobskii and Zoya A. Starikova

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/ejoc.200800948

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      Experimental and theoretical studies of a series of 1,8-bis(dialkylamino)-4,5-dinitronaphthalenes and a peri-dialdehyde analogue have unexpectedly disclosed essentially higher π-acceptor ability of the CHOgroups in the solid and gas phase compared to the NO2 groups. In solution, the through-conjugation is almost equally effective for all molecules, with some predominance of the nitro compounds.

    12. Click Mannich Reaction

      Pronounced Catalytic Effect of a Micellar Solution of Sodium Dodecylsulfate (SDS) Upon a Three-Component Reaction of Aldehydes, Amines, and Ketones Under Neutral Conditions (pages 1249–1255)

      Abbas Ali Jafari, Fatemeh Moradgholi and Fatemeh Tamaddon

      Version of Record online: 20 JAN 2009 | DOI: 10.1002/ejoc.200801037

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      A micellar solution of sodium dodecylsulfate (SDS) efficiently catalyzes a three-component Mannich reaction in neutral pure water at room temperature. The products precipitate in good to excellent yields. The salient features of this protocol include theuse of water as a evironmentally friendly solvent, low SDS loading, neutral conditions, high yields, excellent regio- and stereoselectivity, and clean reaction profiles.

    13. Cyclopeptide Natural Products

      Omphalotins E–I, Five Oxidatively Modified Nematicidal Cyclopeptides from Omphalotus olearius (pages 1256–1262)

      Johannes C. Liermann, Till Opatz, Heinz Kolshorn, Luis Antelo, Carolin Hof and Heidrun Anke

      Version of Record online: 29 JAN 2009 | DOI: 10.1002/ejoc.200801068

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      Omphalotins E–I, modified cyclododecapeptides, were isolated from cultures of Omphalotus olearius. Four of the five omphalotins contained an unprecedented N-hydroxylated tryptophan derivative. All compounds exhibited strong and selective nematicidal activity against the plant pathogen Meloidogyne incognita, whereas no cytotoxic effects were found.

    14. Biomimetic Dioxygen Reduction

      Synthesis and Studies of a Super-Structured Porphyrin Derivative – A Potential Building Block for CcO Mimic Models (pages 1263–1268)

      Georgios Charalambidis, Kalliopi Ladomenou, Bernard Boitrel and Athanassios G. Coutsolelos

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/ejoc.200801122

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      Fe and Fe-Cu complexes of a super-structured porphyrin derivative have been studied for their ability to reduce dioxygen once adsorbed onto the surface of a rotating graphite electrode.

    15. Cycloaddition Reactions

      Cycloaddition Reactions of 1-Alkyl-3,4,5-triphenyl-1,2-diphosphacyclopenta-2,4-dienes (pages 1269–1274)

      Vasili Miluykov, Ilya Bezkishko, Almaz Zagidullin, Oleg Sinyashin, Peter Lönnecke and Evamarie Hey-Hawkins

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/ejoc.200801181

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      1-Alkyl-3,4,5-triphenyl-1,2-diphosphacyclopenta-2,4-dienes 1 can act both as dienes and as dienophiles in cycloaddition reactions, similar to 2H-phospholes. However, in contrast to 2H-phospholes, the cyclodimerization reactions of 1 occur only under harsh reaction conditions to give a [2+2] cycloaddition product.

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