European Journal of Organic Chemistry

Cover image for Vol. 2011 Issue 19

July 2011

Volume 2011, Issue 19

Pages 3379–3530

  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. Pyrrolopyrrole Cyanines: Effect of Substituents on Optical Properties (Eur. J. Org. Chem. 19/2011)

      Georg M. Fischer, Matthias K. Klein, Ewald Daltrozzo and Andreas Zumbusch

      Version of Record online: 24 JUN 2011 | DOI: 10.1002/ejoc.201190048

  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. Enzyme Catalytic Promiscuity

      Biocatalytic Promiscuity (pages 3391–3401)

      Maria Svedendahl Humble and Per Berglund

      Version of Record online: 17 MAY 2011 | DOI: 10.1002/ejoc.201001664

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      Enzyme catalytic promiscuity, which can allow application of enzymes for non-natural reactions, is a recently recognised frontier in biocatalysis. This behaviour can be found in nature in the form of a secondary activity of an enzyme or can be developed by protein engineering. Recent examples that might provide new tools for synthetic chemists are considered from a biocatalytic perspective.

  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. Cyclization Reaction

      Cyclization Reaction of 2-Azido-1-(2-hydroxyphenyl)ethanones with Terminal Alkynoates Catalyzed by 4-Dimethylaminopyridine (DMAP): Synthesis of 2-Aminobenzofuran-3(2H)-one Derivatives (pages 3403–3406)

      Ling-Guo Meng, Ni-Lin Ge, Ming-Ming Yang and Lei Wang

      Version of Record online: 17 MAY 2011 | DOI: 10.1002/ejoc.201100250

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      In the reaction of 2-azido-1-(2-hydroxyphenyl)ethanones with terminal alkynoates catalyzed by 4-dimethylaminopyridine (DMAP) at room temperature in CH2Cl2,2-aminobenzofuran-3(2H)-one derivatives were formed in moderate to good yields. The method contains a transformation from the azido to the amino group.

    2. Asymmetric Cyanosilylation

      Fine Modification of Salen Ligands – Effects on the Salen–Ti-Catalyzed Asymmetric Cyanosilylation of Aldehydes (pages 3407–3411)

      Chengwei Lv, Qigan Cheng, Daqian Xu, Shoufeng Wang, Chungu Xia and Wei Sun

      Version of Record online: 19 MAY 2011 | DOI: 10.1002/ejoc.201100319

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      The catalytic activity and the asymmetric induction ability of bifunctional N-oxide salen–Ti complexes and a pyrrolidine salen–Ti complex together with achiral N-oxide were compared. Both enantiomers of trimethylsilyl ethers of cyanohydrins could be prepared by using the above two dual-activation catalytic systems, which are based on the same chiral diamine collar derived from L-tartaric acid.

    3. Radical Reactions

      Synthesis of Phosphonylated and Thiolated Indenones by Manganese(III)-Mediated Addition of Phosphorus- and Sulfur-Centered Radicals to 1,3-Diarylpropynones (pages 3412–3415)

      Jun Zhou, Guang-Liang Zhang, Jian-Ping Zou and Wei Zhang

      Version of Record online: 24 MAY 2011 | DOI: 10.1002/ejoc.201100486

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      Phosphorus- or sulfur-centered radicals generated from the reaction of manganese(III) acetate with dialkyl phosphonates or arylthiols undergo selective additions toconjugated alkynes followed by cyclization and rearomatization to afford 2-phosphonyl or 2-thioaryl-substituted indenones in fair to good yields.

    4. Butenolide Synthesis

      A Synthetic Route to α-Substituted Butenolides: Enantioselective Synthesis of (+)-Ancepsenolide (pages 3416–3419)

      Cynthia Ghobril, Jérémy Kister and Rachid Baati

      Version of Record online: 18 MAY 2011 | DOI: 10.1002/ejoc.201100491

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      A variety of α-alkylated butenolides were efficiently synthesized in four steps starting from commercially available tetronic acidand carboxylic acids. This new synthetic route was successfully applied to the total synthesis of (+)-ancepsenolide.

  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. Infrared Dyes

      Pyrrolopyrrole Cyanines: Effect of Substituents on Optical Properties (pages 3421–3429)

      Georg M. Fischer, Matthias K. Klein, Ewald Daltrozzo and Andreas Zumbusch

      Version of Record online: 24 MAY 2011 | DOI: 10.1002/ejoc.201100108

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      Syntheses and optical properties of pyrrolopyrrole cyanines (PPCys) with different substituents at the terminal heteroaromatic moieties are described. The relationship between molecular structure and optical properties is discussed. By suitable substitution, the absorption and fluorescence maxima of the chromophore can be tuned in a range between 690 and 845 nm.

    2. Asymmetric Synthesis

      A Tandem Isomerization–Mannich Reaction for the Enantioselective Synthesis of β-Amino Ketones and β-Amino Alcohols with Applications as Key Intermediates for ent-Nikkomycins and ent-Funebrine (pages 3430–3436)

      Hai Thuong Cao, Thierry Roisnel, Alain Valleix and René Grée

      Version of Record online: 17 MAY 2011 | DOI: 10.1002/ejoc.201100352

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      A tandem isomerization–Mannich reaction of allylic alcohols and N-tert-butanesulfinimines gave β-amino ketones in good yields and excellent enantioselectivities. This method was used for the enantioselective synthesis of corresponding β-amino alcohols and also for key intermediates in the preparation of ent-nikkomycins or ent-funebrine.

    3. β-Lactam Lipopeptide Synthesis

      Asymmetric Synthesis of New β-Lactam Lipopeptides as Bacterial Signal Peptidase I Inhibitors (pages 3437–3449)

      Céline Crauste, Matheus Froeyen, Jozef Anné and Piet Herdewijn

      Version of Record online: 20 MAY 2011 | DOI: 10.1002/ejoc.201100148

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      We present the design, asymmetric synthesis, and biological evaluation of novel β-lactam lipopeptides, inhibitors of the signal peptidase I, an essential bacterial enzyme for the viability of both Gram-negative and Gram-positive bacteria. The importance of the azetidinone moiety is demonstrated and can serve as a starting point to improve the structure of these new kinds of SPase I inhibitors.

    4. Synthesis of Nucleoside Phosphonates

      Synthesis of 3′-S-Phosphonomethyl-Modified Nucleoside Phosphonates with a 3′-Deoxy-3′-thio-α-L-threosyl Sugar Moiety (pages 3450–3457)

      Qiuya Huang and Piet Herdewijn

      Version of Record online: 20 MAY 2011 | DOI: 10.1002/ejoc.201100177

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      3′-S-Phosphonomethyl-modified nucleoside phosphonates with a 3′-deoxy-3′-thio-α-L-threosyl sugar moiety and the 2′-deoxy analogues have been synthesized starting from D-xylose and (S)-β-hydroxy-γ-butyrolactone, respectively. All these compounds were evaluated for their in vitro activity against HIV, HCV, and RSV as well as their cytotoxicity.

    5. Arsenic Ylide Mediated Aziridination

      Computational Insights into the Roles of Steric and Electrostatic Interactions in Arsenic Ylide Mediated Aziridination Reactions (pages 3458–3466)

      Madhavan Jaccob and Ponnambalam Venuvanalingam

      Version of Record online: 24 MAY 2011 | DOI: 10.1002/ejoc.201100162

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      Differences in the stabilities of the addition transition states and the low trans selectivity of arsenic ylide mediated aziridination reactions are explained on the basis of steric and weak C–H···O hydrogen-bonding interactions.

    6. Amino Acids

      A Straightforward Approach towards Isoxazoline Amino Acid Esters by Domino Michael Additions/Nitrile Oxide Cycloadditions (pages 3467–3473)

      Lisa Wirtz and Uli Kazmaier

      Version of Record online: 18 MAY 2011 | DOI: 10.1002/ejoc.201100233

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      The syntheses of new isoxazoline aminoacids are described based on a domino Michael addition/nitrile oxide formation/[3+2] cycloaddition approach. Chelated amino acid ester enolates can be added to nitroalkenes, and the nitronates generated are directly converted into nitrile oxides. These can be trapped intramolecularly by alkenes, giving rise to various types of heterocyclic amino acids.

    7. Direct Arylation

      C–H Bond Functionalization of Arylpyrimidines Catalyzed by an in situ Generated Ruthenium(II) Carboxylate System and the Construction of Tris(heteroaryl)-Substituted Benzenes (pages 3474–3481)

      Bogdan Štefane, Jan Fabris and Franc Požgan

      Version of Record online: 13 MAY 2011 | DOI: 10.1002/ejoc.201100238

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      A simple and effective method was developed for a high-yielding phenylpyrimidinemetalation–arylation with an RuII catalytic system.

    8. Multicomponent Reaction

      Expeditious Construction of Spiro-Pyrrolidines by an Autocatalytic One-Pot, Five-Component, 1,3-Dipolar Cycloaddition of in situ Generated Azomethine Ylides and Olefinic Dipolarophiles (pages 3482–3490)

      Ming Li, Fu-Meng Gong, Li-Rong Wen and Zhao-Rui Li

      Version of Record online: 17 MAY 2011 | DOI: 10.1002/ejoc.201100297

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      The highly regio- and stereoselective synthesis of new spiro-pyrrolodines by a combination of a five-component tandemKnoevenagel reaction with a [3+2] dipolarcycloaddition is described, for which azomethine ylides and olefinic dipolarophiles are generated in situ.

    9. Dithienyl Polyphenylene Oxidation

      Oxidative Bond Formation in Dithienyl Polyphenylenes: Optical and Electrochemical Consequences (pages 3491–3499)

      Colin J. Martin, Belen Gil, Sarath D. Perera and Sylvia M. Draper

      Version of Record online: 24 MAY 2011 | DOI: 10.1002/ejoc.201100332

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      Disulfur-containing polyaromatic hydrocarbons were prepared by the oxidative cyclodehydrogenation of a series of dithienyl polyphenylenes. The formation of intra- and intermolecular C–C bond-fusion products was found to be dependent on theposition of S in the thienyl precursor. A photochemical, electrochemical, and spectroelectrochemical investigation was carried out for both the reaction and the products formed in each case.

    10. Transannular Interactions

      Stereochemistry of 2,6-Diaminoadamantane Salts: Transannular Interactions (pages 3500–3506)

      Robert Glaser, Avital Steinberg, Marina Šekutor, Frank Rominger, Oliver Trapp and Kata Mlinarić-Majerski

      Version of Record online: 24 MAY 2011 | DOI: 10.1002/ejoc.201001635

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      New adamantane-2,6-diammonium salts were prepared and their solid-state stereochemistry was studied. NMe3 or NHMe2 groups attached to adamantane 2- and 6-positions bear a striking resemblance to axial or iPr units on cyclohexane. An N–H proton or a bulkier N-methyl group points inward towards the center of an adamantane cyclohexyl fragment.

    11. Asymmetric Michael Addition

      Chiral Thiourea-Catalyzed Asymmetric Michael Addition of β-Oxo Phosphonate to Nitro Olefins: Convenient Synthesis of Optically Active β-Oxo Phosphonates (pages 3507–3513)

      Kuang Hu, Tao Liu, A. D. Lu, Yunfeng Liu, Youming Wang, Guiping Wu, Zhenghong Zhou and Chuchi Tang

      Version of Record online: 17 MAY 2011 | DOI: 10.1002/ejoc.201100029

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      A direct and atom-economic approach to the preparation of synthetically and biologically valuable optically active acyclic α-substituted β-oxo phosphonates with high levels of enantioselectivity (up to 98 % ee)has been developed that involves chiral thiourea-catalyzed asymmetric Michael addition of β-oxo phosphonates to nitro olefins.

    12. Sequential One-Pot Reactions

      Sequential Combination of Ruthenium-, Base-, and Gold-Catalysis – A New Approach to the Synthesis of Medicinally Important Heterocycles (pages 3514–3522)

      Dhevalapally B. Ramachary and Vidadala V. Narayana

      Version of Record online: 24 MAY 2011 | DOI: 10.1002/ejoc.201100040

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      A novel process for the synthesis of highly substituted, medicinally important heterocycles was achieved through the sequential combination of ring-closing methathesis, base-induced ring opening, hydroamination, and Diels–Alder reaction of functionalized allyl-(2-allylphenyl)amines in the presence of a catalytic amount of [Ru], base, and [Au] (see scheme).

    13. Stereoselectivity via Epizirconation

      Versatile Zirconium Reductants and Carbon–Carbon Coupling Agents Selectively Accessible from the 2:1 Molar Aggregate of n-Butyllithium and Zirconium(IV) Salts (pages 3523–3530)

      John J. Eisch, John N. Gitua and Kun Yu

      Version of Record online: 26 MAY 2011 | DOI: 10.1002/ejoc.201100307

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      The aggregate 2 nBuLi·ZrE4 (E = Cl, OEt) in THF undergoes highly selective reactions with benzaldehyde controllable by temperature: 1) at –78 °C carbolithiation gives 1-phenyl-1-pentanol; 2) at 25 °C benzyl alcohol is exclusively formed; and 3) after reflux reductive dimerization to the glycol by ZrE2 takes place with high selectivity (rac/meso ≈ 95:5).

  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
      N-(Di)icosyl-Substituted Benzo[a]phenoxazinium Chlorides: Synthesis and Evaluation as Near-Infrared Membrane Probes

      Sarala Naik, Carla M. A. Alves, Paulo J. G. Coutinho and M. Sameiro T. Gonçalves

      Version of Record online: 24 MAY 2011 | DOI: 10.1002/ejoc.201100653

      This article corrects:

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