European Journal of Organic Chemistry

Cover image for Vol. 2014 Issue 34

December 2014

Volume 2014, Issue 34

Pages 7509–7725

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correspondence
    1. You have free access to this content
      Synthesis of a Photostable Energy-Transfer Pair for “DNA Traffic Lights” (Eur. J. Org. Chem. 34/2014)

      Peggy R. Bohländer and Hans-Achim Wagenknecht

      Article first published online: 21 NOV 2014 | DOI: 10.1002/ejoc.201490096

      Thumbnail image of graphical abstract

      The cover picture shows the green-to-red fluorescence color change upon annealing of a single-stranded oligonucleotide to double-stranded DNA. The color change is based on efficient energy transfer between two dyes that are covalently attached to a 2′-position in each oligonucleotide. Both dyes are highly photostable, which is a key requirement for using “DNA traffic lights” in long-term cellular and molecular imaging applications. Details are discussed in the Short Communication by P. R. Bohländer and H.-A. Wagenknecht on. 7547 ff.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correspondence
    1. Graphical Abstract: Eur. J. Org. Chem. 34/2014 (pages 7509–7517)

      Article first published online: 21 NOV 2014 | DOI: 10.1002/ejoc.201490098

  3. News

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

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

      2-Nitroglycals: Versatile Building Blocks for the Synthesis of 2-Aminoglycosides (pages 7525–7546)

      Thierry Delaunay, Thomas Poisson, Philippe Jubault and Xavier Pannecoucke

      Article first published online: 12 SEP 2014 | DOI: 10.1002/ejoc.201402805

      Thumbnail image of graphical abstract

      Nitration of glycals gives access to the versatile 2-nitroglycal derivatives. These key building blocks are used for the synthesis of potent biologically active compounds. This review highlights the chemistry of 2-nitroglycals and their applications.

  5. Short Communications

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

      Synthesis of a Photostable Energy-Transfer Pair for “DNA Traffic Lights” (pages 7547–7551)

      Peggy R. Bohländer and Hans-Achim Wagenknecht

      Article first published online: 6 OCT 2014 | DOI: 10.1002/ejoc.201403119

      Thumbnail image of graphical abstract

      Slow photobleaching: A new cyano-substituted thiazole red derivative as a red emitter and a novel green fluorescent donor dye of the cyanine styryl type can be combined into an energy-transfer pair in DNA with excellent photostability, large wavelength shift, and good color contrast ratio.

    2. Nitrogen Heterocycles

      Iron-Catalyzed [4C+1N] Cyclization of 4-Acetylenic Ketones with Primary Amines: Synthesis of 5-(Aryl)alkylidene-4,5-dihydropyrroles (pages 7552–7555)

      Bo Sun, Quan Ma, Yeming Wang, Yuegang Zhao, Peiqiu Liao and Xihe Bi

      Article first published online: 28 OCT 2014 | DOI: 10.1002/ejoc.201403097

      Thumbnail image of graphical abstract

      The iron-catalyzed [4C+1N] cyclization of 4-acetylenic ketones with primary amines in 1,5-pentanediol provides an environmentally friendly route to fully substituted 4,5-dihydropyrroles.

    3. Allylation

      Enantioselective Allylation of tert-Butyldimethylsilyl-Protected Vanillin and Synthesis of a Lignan Derivative Isolated from Machilus wangchiana (pages 7556–7560)

      Timothée Cadart, Petr Koukal and Martin Kotora

      Article first published online: 29 OCT 2014 | DOI: 10.1002/ejoc.201403094

      Thumbnail image of graphical abstract

      Enantioselective allylation and crotylation of tert-butyldimethylsilyl (TBS) protected vanillin proceeds with high asymmetric induction (92–96 % ee) by using different catalytic systems. The product of crotylation is converted into the unnatural diastereoisomer of a recently isolated lignan derivative.

    4. Terpenoids

      Prins–Arylthiolation Reaction on Terpenoids: Diastereoselective Synthesis of 4-Arylthiooctahydro-2H-chromenes (pages 7561–7565)

      Barnali Sarmah, Gakul Baishya and Rajani K. Baruah

      Article first published online: 29 OCT 2014 | DOI: 10.1002/ejoc.201403080

      Thumbnail image of graphical abstract

      (–)-Isopulegol undergoes Prins–arylthiolation with aldehydes and cyclohexanone in the presence of HBF4·OEt2 to generate a library of 4-arylthio-octahydro-2H-chromene derivatives in good to excellent yields with moderate to high cis selectivity at ambient temperature in CH2Cl2. HBF4·OEt2 as a catalyst outshines CF3CO2H, which is generally used in excess amounts in Prins cyclization and domino Prins–arylthiolation reactions.

    5. Oligonucleotide Labeling

      Design of a Ribosyltriazole-Annulated Cyclooctyne for Oligonucleotide Labeling by Strain-Promoted Alkyne–Azide Cycloaddition (pages 7566–7571)

      Pieter van Delft, Wilbert de Witte, Nico J. Meeuwenoord, Gerbrand J. van der Heden van Noort, Frank Versluis, Rene C. L. Olsthoorn, Herman S. Overkleeft, Gijs A. van der Marel and Dmitri V. Filippov

      Article first published online: 22 OCT 2014 | DOI: 10.1002/ejoc.201403086

      Thumbnail image of graphical abstract

      The synthesis of a triazole-annulated ribose cyclooctyne phosphoramidite and its subsequent use in the automated solid-phase synthesis of oligonucleotides is described. Strain-induced azide to alkyne [2+3] Huisgen dipolar cycloaddition of the cyclooctyne-containing oligonucleotides with azide-containing fluorescent dyes yields labeled oligonucleotides, including an example of a DNA–RNA duplex; TBDMS = tert-butyldimethylsilyl, DMTr = 4,4′-dimethoxytrityl.

    6. Total Synthesis

      Triphosgene-Mediated Couplings in the Solid Phase: Total Synthesis of Brachystemin A (pages 7572–7576)

      Lijing Fang, Chunlei Wu, Zaidan Yu, Peng Shang, Yongxian Cheng, Yuefeng Peng and Wu Su

      Article first published online: 21 OCT 2014 | DOI: 10.1002/ejoc.201403145

      Thumbnail image of graphical abstract

      A highly efficient protocol for the triphosgene-mediated solid-phase coupling of proteinogenic amino acids is developed and applied to the first total synthesis of the bioactive natural octacyclopeptide brachystemin A.

    7. Asymmetric Synthesis

      Stereoselective Synthesis of Highly Substituted α-Silylamines from Silylmethyl Azides under Ru Catalysis (pages 7577–7581)

      Wook Jeong, Jungjoon Kim, Jaiwook Park and Young Ho Rhee

      Article first published online: 22 OCT 2014 | DOI: 10.1002/ejoc.201403200

      Thumbnail image of graphical abstract

      A diastereo- and enantioselective synthesis of highly functionalized α-silyl homoallylic amines is reported. This new reaction is promoted by unique access to N-unsubstituted α-silylimines from azide precursors, which is conducted under mild Ru catalysis and photolytic conditions; pin = pinacolyl.

    8. Total Synthesis

      An Economical and Practical Synthesis of rac-(Z)-β-Santalol: Application of a Scriabine-Inspired Reaction to Alkenes Results in the One-Step Preparation of a Key Intermediate (pages 7582–7585)

      Anthony A. Birkbeck, Xavier Marquet, Pascal Millet and Hervé Pamingle

      Article first published online: 29 OCT 2014 | DOI: 10.1002/ejoc.201403219

      Thumbnail image of graphical abstract

      An economical and scalable synthesis of rac-(Z)-β-santalol is accomplished. The key coupling step is based on a Scriabine-inspired reaction of a dienyl diacetate substrate and an alkene. The total synthesis is achieved in five steps (longest linear sequence) in 19 % overall yield from cyclopentadiene; Cp* = C5Me5, cod = 1,5-cyclooctadiene, Tf = trifluoromethylsulfonyl.

    9. C–H Functionalization

      Nickel-Catalyzed Decarboxylative Arylation of Heteroarenes through sp2 C–H Functionalization (pages 7586–7589)

      Ke Yang, Peng Wang, Cheng Zhang, Adnan A. Kadi, Hoong-Kun Fun, Yan Zhang and Hongjian Lu

      Article first published online: 21 OCT 2014 | DOI: 10.1002/ejoc.201403234

      Thumbnail image of graphical abstract

      The nickel-catalyzed direct decarboxylative arylation of hetereoarenes with benzoic acids through an sp2 C–H functionalization process is reported. This transformation provides the first examples of decarboxylative cross-coupling reactions with aromatic acids through nickel catalysis. IPr = 1,3-Bis(2,6-diisopropylphenyl)-imidazol-2-ylidene, BQ = 1,4-benzoquinone.

    10. Flow Chemistry

      High-Temperature Synthesis of Amides from Alcohols or Aldehydes by Using Flow Chemistry (pages 7590–7593)

      Nida Ambreen and Thomas Wirth

      Article first published online: 28 OCT 2014 | DOI: 10.1002/ejoc.201403280

      Thumbnail image of graphical abstract

      An efficient and fast conversion of aliphatic and aromatic alcohols or aldehydes into the corresponding primary amides is successfully achieved at high temperatures by using flow chemistry.

  6. Full Papers

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

      Role of Side-Chain Bioisosteres in Determining the Binding Affinity of Click Chemistry Derived RGD Peptidomimetics to αvβ3 Integrin (pages 7595–7604)

      Pierangelo Fabbrizzi, Gloria Menchi, Silvia Raspanti, Antonio Guarna and Andrea Trabocchi

      Article first published online: 24 OCT 2014 | DOI: 10.1002/ejoc.201403129

      Thumbnail image of graphical abstract

      Click chemistry was used to build a series of nonpeptide Arg-Gly-Asp (RGD) peptidomimetics. Integrin binding assays revealed heterocyclic guanidine bioisosteres that showed binding activity and also indicated a minor role played by the aromatics on the azide fragment. Modelling showed that the triazole and 2-aminopyridine rings interact with Tyr178 of αvβ3 integrin.

    2. DNA Intercalators

      DNA Recognition with Polycyclic-Aromatic-Hydrocarbon-Presenting Calixarene Conjugates (pages 7605–7613)

      Antonio Rescifina, Chiara Zagni, Placido G. Mineo, Salvatore V. Giofrè, Ugo Chiacchio, Stefano Tommasone, Carmen Talotta, Carmine Gaeta and Placido Neri

      Article first published online: 21 OCT 2014 | DOI: 10.1002/ejoc.201403050

      Thumbnail image of graphical abstract

      We have synthesized polycyclic-aromatic-hydrocarbon-presenting (PAH-presenting) calix[4]arene conjugates with pyrenylisoxazolidine moieties linked to the calix[4]arene exo rim as DNA-intercalating agents. The most potent one showed an IC50 of 95 nM for FTC133 cells; circular dichroism and docking studies suggest that it acts as a monointercalator that penetrates from the minor groove.

    3. Linezolid Synthesis

      Convenient Synthesis of the Antibiotic Linezolid via an Oxazolidine-2,4-dione Intermediate Derived from the Chiral Building Block Isoserine (pages 7614–7620)

      Arianna Greco, Rossella De Marco, Sara Tani, Daria Giacomini, Paola Galletti, Alessandra Tolomelli, Eusebio Juaristi and Luca Gentilucci

      Article first published online: 28 OCT 2014 | DOI: 10.1002/ejoc.201402888

      Thumbnail image of graphical abstract

      The 1,3-oxazolidin-2-one core of linezolid was obtained from isoserine in just three steps and with almost quantitative overall yield; the key features of the protocol are the expedient formation of the intermediate oxazolidine-2,4-dione, and its regioselective reduction at the 4-position.

    4. Lectin-Binding Galactoclusters

      Synthesis of Galactoclusters by Metal-Free Thiol “Click Chemistry” and Their Binding Affinities for Pseudomonas aeruginosa Lectin LecA (pages 7621–7630)

      Caroline Ligeour, Lucie Dupin, Alberto Marra, Gérard Vergoten, Albert Meyer, Alessandro Dondoni, Eliane Souteyrand, Jean-Jacques Vasseur, Yann Chevolot and François Morvan

      Article first published online: 21 OCT 2014 | DOI: 10.1002/ejoc.201402902

      Thumbnail image of graphical abstract

      Galactocluster oligonucleotide conjugates were synthesised by a combination of nucleic acid chemistry and metal-free thiol reactions (i.e., thiol Michael-type addition or nucleophilic displacement of bromoacetamide group by a thiol). Their binding to LecA was studied with a DNA-based microarray.

    5. Nitrogen Heterocycles

      A Versatile Protocol for the Synthesis of Pyrazolyl-Substituted Pyridinium and Guanidinium Salts from Pyridone and Urea Derivatives (pages 7631–7642)

      Antje K. C. Echterhoff, Sivathmeehan Yogendra, Jutta Kösters, Roland Fischer and Jan J. Weigand

      Article first published online: 27 OCT 2014 | DOI: 10.1002/ejoc.201403057

      Thumbnail image of graphical abstract

      The Janus head type diphosphorus trication (pyr3P2)3+ (pyr = 3,5-dimethylpyrazolyl) is used as pyrazolyl-transfer reagent to convert 2-pyridones, 4-pyridones, and urea derivatives to pyrazolyl-substituted pyridinium or guanidinium triflate salts. The lactam–lactim tautomerism controls the reaction outcome. Thus, under lactim-favoring conditions, tripyridyl phosphites are formed in these reactions.

    6. Oligomer Conformations

      Synthesis and Structural Characterization of 2:1 [α/Aza]-oligomers (pages 7643–7650)

      Zhou Zhou, Cheng Deng, Cécile Abbas, Claude Didierjean, Marie-Christine Averlant-Petit, Jacques Bodiguel, Régis Vanderesse and Brigitte Jamart-Grégoire

      Article first published online: 21 OCT 2014 | DOI: 10.1002/ejoc.201402628

      Thumbnail image of graphical abstract

      The synthesis of heterochiral and homochiral 2:1 [α/aza]-oligomers is described. These oligomers exhibit folding structures in both solution and in the solid state that are attributable to β-turn generating processes.

    7. Heterocyclization

      Heterocycle-to-Heterocycle Route to Quinoline-4-amines: Reductive Heterocyclization of 3-(2-Nitrophenyl)isoxazoles (pages 7651–7657)

      Keith C. Coffman, Vy Duong, Alex L. Bagdasarian, James C. Fettinger, Makhluf J. Haddadin and Mark J. Kurth

      Article first published online: 15 OCT 2014 | DOI: 10.1002/ejoc.201403065

      Thumbnail image of graphical abstract

      A variety of quinoline-4-amines were synthesized from 3-(2-nitrophenyl)isoxazoles via reductive heterocyclization with Zn0 or Fe0 and HOAc; starting isoxazoles were synthesized from readily available starting materials. A brief survey of tolerated functional groups was performed and a few examples of 10-amino-3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-ones were also synthesized and diversified.

    8. Carbohydrates

      Synthesis of Vicinal Diketoses by Using a Metathesis–Hydroxylation–Oxidation Sequence (pages 7658–7663)

      Melchior Menzel and Thomas Ziegler

      Article first published online: 24 OCT 2014 | DOI: 10.1002/ejoc.201403140

      Thumbnail image of graphical abstract

      The attempted structure elucidation and total synthesis of a naturally occurring antidiabetic drug led to the synthesis of two higher monosaccharides by using an olefination, cross-coupling, and oxidation reaction sequence. This synthetic strategy paves the way to a new class of substances that is not yet well investigated.

    9. Nitrogen Heterocycles

      Mechanistic Study of a Complementary Reaction System that Easily Affords Quinazoline and Perimidine Derivatives (pages 7664–7674)

      Zerong Daniel Wang, Joshua Eilander, Motoko Yoshida and Tianzhi Wang

      Article first published online: 15 OCT 2014 | DOI: 10.1002/ejoc.201402854

      Thumbnail image of graphical abstract

      The mechanism of a novel reaction to form substituted quinazoline and perimidine derivatives has been elucidated. This reaction involves the thermal decomposition of thiourea to form carbodiimide and H2S, the former couples with 2-aminobenzophenone to form 4-phenylquinazolin-2(1H)-imine intermediate, which is then reduced and converted into 4-phenylquinazoline.

    10. Nucleophilic Aromatic Substitution

      SNH- and SNipso-Arylamination of 1,3,7-Triazapyrenes (pages 7675–7683)

      Ivan Borovlev, Oleg Demidov, Nadezhda Saigakova and Gulminat Amangasieva

      Article first published online: 21 OCT 2014 | DOI: 10.1002/ejoc.201402891

      Thumbnail image of graphical abstract

      6-Arylamino-1,3,7-triazapyrenes were obtained from 1,3,7-triazapyrenes through an oxidative SNH-process, whereas 6,8-bis(arylamino)-1,3,7-triazapyrenes and 6-alkoxy-8-arylamino-1,3,7-triazapyrenes were synthesized from 6,8-dialkoxy-1,3,7-triazapyrenes, using SNipso methodology. In all cases, the corresponding sodium arylamides were used as reactants.

    11. Oligoprenyl Diphosphates

      Synthesis of Isotopically Labelled Oligoprenyl Diphosphates and Their Application in Mechanistic Investigations of Terpene Cyclases (pages 7684–7691)

      Christian A. Citron, Patrick Rabe, Lena Barra, Chiaki Nakano, Tsutomu Hoshino and Jeroen S. Dickschat

      Article first published online: 24 OCT 2014 | DOI: 10.1002/ejoc.201403002

      Thumbnail image of graphical abstract

      A synthesis of isotopically labelled oligoprenyl diphosphates was developed. This method allows for the introduction of labelling into every position or combination of positions. [14-2H]Geranylgeranyl diphosphate was used in an incubation experiment with tuberculosinyl diphosphate synthase from Mycobacterium tuberculosis, giving insight into the stereochemical course of the terpene cyclase reaction.

    12. Enzymatic Kinetic Resolution

      Enzyme-Catalyzed Kinetic Resolution of 2,2,2-Trifluoro-1-(heteroaryl)ethanols: Experimental and Docking Studies (pages 7692–7698)

      Olexandr V. Kucher, Anastasiya O. Kolodiazhnaya, Oleg B. Smolii, Dmytro V. Prisuazhnyk, Katerina A. Tolmacheva, Olga A. Zaporozhets, Yurii S. Moroz, Pavel K. Mykhailiuk and Andrey A. Tolmachev

      Article first published online: 21 OCT 2014 | DOI: 10.1002/ejoc.201403013

      Thumbnail image of graphical abstract

      Enantiopure (R) and (S) isomers of fourteen 2,2,2-trifluoro-1-(heteroaryl)ethanols were obtained by using an enzyme-catalyzed kinetic resolution of the corresponding racemic mixtures. The procedure involves an acylation and a hydrolysis step in the presence of Burkholderia cepacia and CAL-B lipase (Candida antarctica lipase B), respectively. The compounds were resolved on a multigram scale.

    13. Supported Pd Catalyst

      A Palladium Catalyst Supported on Carbon-Coated Cobalt Nanoparticles – Preparation of Palladium-Free Biaryls by Suzuki–Miyaura Reactions in Ethanol (pages 7699–7706)

      Antoine Derible, Carine Diebold, Joseph Dentzer, Roger Gadiou, Jean-Michel Becht and Claude Le Drian

      Article first published online: 21 OCT 2014 | DOI: 10.1002/ejoc.201403038

      Thumbnail image of graphical abstract

      A Pd catalyst supported on Co/C nanoparticles is easily prepared and allows very efficient Suzuki–Miyaura reactions in which only 1 μequiv. of Pd is lost in the reaction medium.

    14. Nitrogen Heterocycles

      Design and Synthesis of 3-Trifluoromethyl-3H-pyrazoles and Further Investigations of Their Transformation to 1H-Pyrazoles (pages 7707–7715)

      Qiang Sha, Haixuan Liu and Yunyang Wei

      Article first published online: 27 OCT 2014 | DOI: 10.1002/ejoc.201403141

      Thumbnail image of graphical abstract

      The synthesis of trifluoromethyl-substituted 3H-pyrazoles by an intramolecular cycloaddition strategy is developed. Subsequently, their wide applications are demonstrated: they (1) react with dioxane by a radical process and (2) undergo [1,5] sigmatropic rearrangements. The products are obtained in high yields and with excellent regioselectivity.

    15. Palladium Catalysis

      Enantioselective Synthesis of Spiroimines by Asymmetric Decarboxylative Alkylation/Isomerization/[3+2]-Cycloaddition Reaction of Azidoalkenes (pages 7716–7720)

      Matt Rambla, Leslie Duroure, Laurent Chabaud and Catherine Guillou

      Article first published online: 24 OCT 2014 | DOI: 10.1002/ejoc.201403161

      Thumbnail image of graphical abstract

      The synthesis of optically active spiroimines, one of the pharmacophores of the marine neurotoxin gymnodimine A, is described. The approach relies on a three-step sequence that includes a palladium-catalyzed asymmetric decarboxylative alkylation, an isomerization and a [3+2]-cycloaddition reaction of an azidoalkene to build the imine.

  7. Correspondence

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

      Phenazines and Their N-Oxides as Products of Cyclization of N-Aryl-2-nitrosoanilines – Disproof of the Reported Homolytic Cross-Coupling Process Leading to Benzo[c]cinnoline Oxides (pages 7721–7725)

      Zbigniew Wróbel, Karolina Stachowska and Andrzej Kwast

      Article first published online: 28 OCT 2014 | DOI: 10.1002/ejoc.201402624

      Thumbnail image of graphical abstract

      No evidence was found for the reported formation of benzo[c]cinnoline oxides in the KOtBu-mediated homolytic cross-coupling reaction of anilines with nitroarenes. Instead, nucleophilic substitution of hydrogen with anilide ion takes place, with formation of intermediate N-aryl-2-nitrosoanilines, which cyclize to phenazines and/or their oxides depending on the reaction conditions and substituents.

SEARCH

SEARCH BY CITATION