European Journal of Organic Chemistry

Cover image for Vol. 2012 Issue 26

September 2012

Volume 2012, Issue 26

Pages 4867–5092

  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
      A peri-Cyclised Naphthalene Dimer: Synthesis and Properties of an Unusual Vilsmeier–Haack Product of 1,3,6,8-Tetramethoxynaphthalene (Eur. J. Org. Chem. 26/2012)

      Michael Pittelkow, Christian B. Nielsen, Theis Brock-Nannestad, Magnus Schau-Magnussen and Jørn B. Christensen

      Version of Record online: 3 SEP 2012 | DOI: 10.1002/ejoc.201290069

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      The cover picture shows the synthesis of a peri-cyclised naphthalene dimer formed by Vilsmeier–Haack formylation of 1,3,6,8-tetramethoxynaphthalene. The cover features a schematic drawing of the H. C. Ørsted Institute at the University of Copenhagen where the research was performed. The stamp featuring H. C. Ørsted is reproduced with the permission of “Post & Tele Museum Danmark” and “Post Danmark”. Details are discussed in the article by M. Pittelkow, J. B. Christensen et al. on p. 4931 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. Oxidative Enolate Coupling

      Oxidative Coupling of Enolates, Enol Silanes, and Enamines: Methods and Natural Product Synthesis (pages 4881–4896)

      Fenghai Guo, Michael D. Clift and Regan J. Thomson

      Version of Record online: 16 JUL 2012 | DOI: 10.1002/ejoc.201200665

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      Recent years have seen the development of several new methods for the oxidative coupling of enolates and related derivatives. This microreview summarizes some key methodology addressing issues of cross-coupling and stereocontrol. The utility of oxidative enolate coupling is highlighted by descriptions of recent strategic applications of the reaction in natural product total synthesis.

  5. Short Communications

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

      Amination of Aryl Halides by Using an Environmentally Benign, Recyclable Copper Catalyst (pages 4897–4901)

      Manna Huang, Leilei Wang, Xinhai Zhu, Zuxing Mao, Daizhi Kuang and Yiqian Wan

      Version of Record online: 9 AUG 2012 | DOI: 10.1002/ejoc.201200787

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      The combination of CuSO4 with naturally occurring sucrose in a biodegradable, aqueous solution of PEG-200 has been confirmed to be a novel, recyclable, and environmentally benign homogeneous catalyst system for the direct amination of aryl halides with NH3·H2O.

    2. Aldehyde Tranformations

      Preparation and Reactions of Aliphatic 2-Pentafluorosulfanyl Aldehydes (pages 4902–4905)

      Silvana C. Ngo, Jin-Hong Lin, Paul R. Savoie, Erica M. Hines, Kaitlin M. Pugliese and John T. Welch

      Version of Record online: 7 AUG 2012 | DOI: 10.1002/ejoc.201200763

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      An efficient method to prepare aliphatic 2-pentafluorosulfanyl aldehydes was developed. An investigation of various aldehyde transformations showed that the pentafluorosulfanyl group was stable under a variety of reaction conditions, and the products were obtained in moderate to good yields.

    3. Morita–Baylis–Hillman Reaction

      Diethylaluminum Iodide Promoted Morita–Baylis–Hillman Reaction of D-Glucose-Derived Densely O-Functionalized Cyclopentenone: Route to α-C-Branched Densely Functionalized Cyclic Enones (pages 4906–4909)

      Partha Ghosal, Sama Ajay, Vikas Bajpai, Brijesh Kumar and Arun K. Shaw

      Version of Record online: 8 AUG 2012 | DOI: 10.1002/ejoc.201200661

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      Morita–Baylis–Hillman (MBH) reaction of carbohydrate derived highly O-functionalized cyclopentenone is described for the first time. The MBH reaction of cyclopentenone 2 with different aldehydes in the presence of diethylaluminum iodide (Et2AlI) proceeded smoothly in moderate to good yields.

    4. Total Synthesis

      Total Synthesis of (+)-Seimatopolide A (pages 4910–4913)

      Chada Raji Reddy, Nagavaram Narsimha Rao and Motatipally Damoder Reddy

      Version of Record online: 8 AUG 2012 | DOI: 10.1002/ejoc.201200732

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      The first total synthesis of a new macrolide, (+)-seimatopolide A, was achieved starting from the natural amino acid L-aspartic acid by using Sharpless asymmetric dihydroxylation, Yamaguchi esterification, and ring-closing metathesis reactions as key steps. The stereochemistry of the natural product was revised.

    5. C–O Cross Coupling

      Trideuteriomethoxylation of Aryl and Heteroaryl Halides (pages 4914–4917)

      Pragyanditi Dash, Manojkumar Janni and S. Peruncheralathan

      Version of Record online: 6 AUG 2012 | DOI: 10.1002/ejoc.201200753

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      The simple and straightforward synthesis of labeled methyl (hetero)aryl ethers via palladium-catalyzed C–O cross-coupling reaction of (hetero)aryl halides with CD3OD was developed. The tBuXPhos ligand is used for the first time in ether synthesis.

    6. Cycloaddition

      CuBr/PMDETA-Mediated Reactions of [60]Fullerene with Active Halides: Preparation of Methano[60]Fullerene Derivatives (pages 4918–4922)

      Hai-Tao Yang, Zong-Yong Tian, Xiao-Jiao Ruan, Min Zhang, Chun-Bao Miao and Xiao-Qiang Sun

      Version of Record online: 2 AUG 2012 | DOI: 10.1002/ejoc.201200759

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      An efficient method for the preparation of methano[60]fullerene derivatives linked with a single electron-withdrawing group has developed through the one-step reaction of [60]fullerene with active halides mediated by CuBr/pentamethyldiethylenetriamine (PMDETA). A plausible reaction mechanism, but not the atom transfer radical process, was proposed.

    7. Conjugate Addition

      Activation of Si–Si Bonds for Copper(I)-Catalyzed Conjugate Silylation (pages 4923–4926)

      Laura Iannazzo and Gary A. Molander

      Version of Record online: 8 AUG 2012 | DOI: 10.1002/ejoc.201200767

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      Alkyl- and vinylsilanes were prepared through copper(I)-catalyzed conjugate addition through activation of Si–Si bonds. Electrophilic substrates such as activated alkenes containing sulfono, cyano, and amido groups were used as acceptors for this transformation, and ester-substituted alkynes also emerged as suitable partners, leading to a new method for the generation of vinylsilanes.

    8. Glycosylation

      Halide Effects on Cyclopropenium Cation Promoted Glycosylation with Deoxy Sugars: Highly α-Selective Glycosylations Using a 3,3-Dibromo-1,2-diphenylcyclopropene Promoter (pages 4927–4930)

      Jason M. Nogueira, John Paul Issa, An-Hsiang Adam Chu, Jordan A. Sisel, Ryan S. Schum and Clay S. Bennett

      Version of Record online: 1 AUG 2012 | DOI: 10.1002/ejoc.201200907

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      α-Selective dehydrative glycosylations are achieved by using a cyclopropenium cation promoter system. The conditions permit glycosylations using 2-deoxy sugar donors without the need to isolate highly reactive intermediates. Yields and selectivity (up to >20:1) are good, and the reaction tolerates a range of substrates, including disarmed donors.

  6. Full Papers

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

      A peri-Cyclised Naphthalene Dimer: Synthesis and Properties of an Unusual Vilsmeier–Haack Product of 1,3,6,8-Tetramethoxynaphthalene (pages 4931–4936)

      Michael Pittelkow, Christian B. Nielsen, Theis Brock-Nannestad, Magnus Schau-Magnussen and Jørn B. Christensen

      Version of Record online: 4 JUL 2012 | DOI: 10.1002/ejoc.201200512

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      The Vilsmeier–Haack reaction (POCl3/DMF) of 1,3,6,8-tetramethoxynaphthalene gave an unusual peri-cyclised dimer as well as the 1-naphthaldehyde. The dimer is a potent donor molecule.

    2. Analytical Methods

      Selective Detection of Nerve Agent Simulants by Using Triarylmethanol-Based Chromogenic Chemodosimeters (pages 4937–4946)

      Ana M. Costero, Margarita Parra, Salvador Gil, Raúl Gotor, Ramón Martínez-Mañez, Félix Sancenón and Santiago Royo

      Version of Record online: 25 JUL 2012 | DOI: 10.1002/ejoc.201200570

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      Triarylmethanol derivatives as visual OFF/ON chromodosimeters of nerve-agent simulants (DCNP and DFP), even in water/acetonitrile (3:1 v/v) solutions, were investigated. The developed compounds were able to act as double probe systems and allowed the selective signalling of DFP. Films of compound 2 were used to detect the simulants in solution and in the vapour phase.

      Corrected by:

      Correction: Selective Detection of Nerve Agent Simulants by Using Triarylmethanol-Based Chromogenic Chemodosimeters

      Vol. 2012, Issue 33, 6662, Version of Record online: 22 OCT 2012

    3. Organic Photovoltaics

      Naphthyl Derivatives Functionalised with Electron Acceptor Units – Synthesis, Electronic Characterisation and DFT Calculations (pages 4947–4953)

      Miquel Planells and Neil Robertson

      Version of Record online: 31 JUL 2012 | DOI: 10.1002/ejoc.201200715

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      A series of unsymmetrical dyes was synthesised and characterised. Their optical and electrochemical properties were tuned by modifying the electron acceptor unit.

    4. Improved Coenzyme Synthesis

      Synthesis of Coenzyme Q10 (pages 4954–4962)

      Eun-Taek Oh, Hee Jin Kim, Jung Taek Oh, Liang Su, Inkyun Yun, Kyunggu Nam, Jae-Hong Min, Joon Woo Kim and Sangho Koo

      Version of Record online: 26 JUL 2012 | DOI: 10.1002/ejoc.201200627

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      An improved synthesis gave CoQ10 in 53 % overall yield from tetramethoxytoluene through Friedel–Crafts allylation with a para-chlorobenzenesulfonyl-substituted C5 allylic chloride and a modified oxidation procedure.

    5. Alkene Reduction

      Nicotinamide-Dependent Ene Reductases as Alternative Biocatalysts for the Reduction of Activated Alkenes (pages 4963–4968)

      Katharina Durchschein, Silvia Wallner, Peter Macheroux, Wilfried Schwab, Thorsten Winkler, Wolfgang Kreis and Kurt Faber

      Version of Record online: 30 JUL 2012 | DOI: 10.1002/ejoc.201200776

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      Electronically activated alkenes have been stereoselectively reduced by using a single-enzyme-cofactor system employing nicotinamide-dependent non-flavin ene reductases.

    6. Synthesis of Substituted Benzyl Homo-C-Ribonucleosides and -Nucleotides as Carba Analogues of Phosphoribosylanthranilate (pages 4969–4981)

      Tomáš Kubelka, Lenka Slavětínská and Michal Hocek

      Version of Record online: 26 JUL 2012 | DOI: 10.1002/ejoc.201200819

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      Novel benzyl C-nucleosides were designed and prepared as carba analogues of phosphoribosylanthranilate, an important intermediate in the biosynthesis of tryptophan.

    7. Multicomponent Reactions

      One-Step Formation both of C–N and of C–O Bonds of N-Alkoxyamides through NHC-Catalyzed Three-Component Reactions of Enals, Nitrosoarenes, and Enones (pages 4982–4987)

      Zhong-Xin Sun and Ying Cheng

      Version of Record online: 25 JUL 2012 | DOI: 10.1002/ejoc.201200525

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      NHC-catalyzed three-component reactions of α,β-unsaturated aldehydes (enals), nitrosoarenes, and α,β-unsaturated ketones (enones) proceeded through a cascade aza-benzoin condensation/oxo-Michael addition sequence to produce N,O-bisfunctionalized N-hydroxylacrylamides in moderate to good yields.

    8. Diaminoconduritol

      Synthesis of a New 2,3-Diaminoconduritol with Conduritol F Structure (pages 4988–4995)

      Zeynep Ekmekci and Metin Balci

      Version of Record online: 25 JUL 2012 | DOI: 10.1002/ejoc.201200582

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      A new 2,3-diaminoconduritol with the conduritol F structure was prepared starting from the known anhydride 3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione, which was successfully converted into the desired diene with bis(carbamate) functional groups. The photooxygenation of the diene followed by cleavage of the peroxide linkage and removal of the protecting groups gave the new 2,3-diaminoconduritol.

    9. Ionic Liquids

      Synthesis of Chiral Room Temperature Ionic Liquids from Amino Acids – Application in Chiral Molecular Recognition (pages 4996–5009)

      Laura González, Belén Altava, Michael Bolte, M. Isabel Burguete, Eduardo García-Verdugo and Santiago V. Luis

      Version of Record online: 26 JUL 2012 | DOI: 10.1002/ejoc.201200607

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      New chiral room temperature ionic liquids, based on an imidazolium group and derived from natural amino acids, have been synthesized and studied as chiral shiftagents for the chiral discrimination of enantiomeric carboxylate salts.

    10. Sulfoxide-Modified Carbohydrates

      Synthesis of Vinyl Sulfoxide-Modified Pent-2-enofuranosides and Hex-2-enopyranosides and Preliminary Studies of Their Reactivity (pages 5010–5017)

      Ananta Kumar Atta, Debanjana Dey, Atanu Bhaumik, Chinmoy Manna, Tarun K. Pal and Tanmaya Pathak

      Version of Record online: 30 JUL 2012 | DOI: 10.1002/ejoc.201200637

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      Oxidation of furanosyl sulfides to sulfoxides afforded both diastereomers. The chirality of the sulfoxide group did not greatly influence the addition patterns of vinyl sulfoxide-modified pent-2-enofuranosides. Oxidation of pyranosyl sulfide gave only one diastereomer and the modified hex-2-enopyranosides significantly influenced the outcome of carbon nucleophile addition to these Michael acceptors.

    11. Domino Reactions

      Total Synthesis of Calothrixins A and B by Palladium-Catalyzed Tandem Cyclization/Cross-Coupling Reaction of Indolylborate (pages 5018–5027)

      Takumi Abe, Toshiaki Ikeda, Tominari Choshi, Satoshi Hibino, Noriyuki Hatae, Eiko Toyata, Reiko Yanada and Minoru Ishikura

      Version of Record online: 26 JUL 2012 | DOI: 10.1002/ejoc.201200657

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      Palladium-catalyzed cross-coupling reaction of indolylborate with vinyl bromide proceeded smoothly, leading to triene. This intermediate was successfully used for the total synthesis of calothrixins A and B.

    12. New Sultams

      Access to a Wide Range of Sultams by Cyclodialkylation of α-Substituted Methanesulfonanilides (pages 5028–5037)

      Valentin A. Rassadin, Daria S. Grosheva, Irina A. Arefeva, Aleksandr A. Tomashevskiy, Victor V. Sokolov and Armin de Meijere

      Version of Record online: 3 AUG 2012 | DOI: 10.1002/ejoc.201200670

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      The intermolecular cyclodialkylation of α-substituted methanesulfonamides constitutes a simple and efficient route to five- and six-membered sultams with α-ethoxycarbonyl-α-methyl or α-aryl substitution. The intramolecular cyclodialkylation of N-(2,3-dibromopropyl)-α-toluenesulfanilides readily leads to bicyclic sultams bearing a cyclopropane ring.

    13. Multicomponent Reactions

      Copper-Catalyzed Decarboxylative Three-Component Reactions for the Synthesis of Imidazo[1,2-a]pyridines (pages 5038–5047)

      Thiruvengadam Palani, Kyungho Park, Manian Rajesh Kumar, Hyun Ming Jung and Sunwoo Lee

      Version of Record online: 31 JUL 2012 | DOI: 10.1002/ejoc.201200679

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      Imidazo[1,2-a]pyridine derivatives were synthesized through three-component coupling reactions of 2-aminopyridines, aldehydes, and alkynecarboxylic acids in the presence of 10 mol-% CuI/Cu(OTf)2

    14. Conformations of Dodecanolactone

      Conformational Studies of Dodecanolactone by Dynamic NMR Spectroscopy and Computational Methods (pages 5048–5053)

      Gurvinder Gill, Diwakar M. Pawar and Eric A. Noe

      Version of Record online: 31 JUL 2012 | DOI: 10.1002/ejoc.201200125

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      The two conformations with populations of 44.5 and 55.5 % found by dynamic NMR analysis of dodecanolactone at –164.2 °C were assigned to 1a and 1b on the basis of calculations. Ab initio calculations of carbon chemical shifts, in addition to free energies, were used in the assignments.

    15. Oligosaccharide Synthesis

      Modular Synthesis of Core Fucosylated N-Glycans (pages 5054–5068)

      Dimitri Ott, Joachim Seifert, Ingo Prahl, Mathäus Niemietz, Joanna Hoffman, Janna Guder, Manuel Mönnich and Carlo Unverzagt

      Version of Record online: 24 JUL 2012 | DOI: 10.1002/ejoc.201200468

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      A modular synthesis of core-fucosylated N-glycans was optimized, leading to the biantennary octasaccharide N-glycan A. Several obstacles to the synthesis of functionalized core trisaccharide building block B were overcome, leading to an improved and efficient protocol for β-mannosylation by intramolecular inversion.

    16. Modeling of Vicriviroc

      Complete Characterization of the 3D Properties of the CCR5 Antagonist Vicriviroc through DFT Calculations, NMR Spectroscopy, and X-ray Analysis (pages 5069–5074)

      Laura Legnani, Diego Colombo, Stefania Villa, Fiorella Meneghetti, Carlo Castellano, Arianna Gelain, Franca Marinone Albini and Lucio Toma

      Version of Record online: 24 JUL 2012 | DOI: 10.1002/ejoc.201200586

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      A complete modeling study of vicriviroc was carried out by using theoretical calculations, and the results were confirmed through a NOESY experiment. Several populated conformations were identified originating from the amido group arrangement as well as chair inversion at the piperazine and piperidine rings and rotations around the bond connecting them.

    17. Solid-Phase Heterocycle Synthesis

      Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyl­iminiums (pages 5075–5084)

      Barbora Vaňková, Lucie Brulíková, Boyuan Wu and Viktor Krchňák

      Version of Record online: 24 JUL 2012 | DOI: 10.1002/ejoc.201200591

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      Straightforward solid-phase synthesis afforded linear precursors for formation of cyclic N-alkyl and N-acyliminiums. Exposure of acyclic resin-bound intermediates to TFA yielded trisubstituted dihydropyrazinones and tetrahydropyrazines, whereas treatment of the same intermediates with a TES-containing cleavage cocktail afforded piperazines and piperazinones.

    18. Synthetic Methods

      Regioselective N-Alkylation of 2-Aminoimidazoles with Alcohols to 2-(N-Alkylamino)imidazoles Catalyzed by the [Cp*IrCl2]2/K2CO3 System (pages 5085–5092)

      Feng Li, Qikai Kang, Haixia Shan, Lin Chen and Jianjiang Xie

      Version of Record online: 1 AUG 2012 | DOI: 10.1002/ejoc.201200698

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      The direct N-alkylation of 2-aminoimidazoles to give the corresponding 2-(N-alkylamino)imidazoles was accomplished using alcohols as alkylating agents in the presence of a [Cp*IrCl2]2/K2CO3 system. The iridium-catalyzed regioselective reaction is simple, efficient, general, and environmentally benign.

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