European Journal of Organic Chemistry

Cover image for Vol. 2014 Issue 13

May 2014

Volume 2014, Issue 13

Pages 2619–2812

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
    1. Design Strategies for Enhanced Hydrogen-Bond Donor Catalysts (Eur. J. Org. Chem. 13/2014)

      Tyler J. Auvil, Andrew G. Schafer and Anita E. Mattson

      Article first published online: 22 APR 2014 | DOI: 10.1002/ejoc.201490033

      Thumbnail image of graphical abstract

      The cover picture shows design elements that have been built into dual hydrogen bond donor (HBD) scaffolds for the purpose of enhancing their catalytic performance. As the power of HBD catalysis continues to grow, chemists can consider taking a do-it-yourself approach to strategically perfecting HBD catalyst scaffolds to achieve high yield and stereocontrol for their desired operation. To help guide efforts in optimal catalyst identification, the Microreview by A. E. Mattson et al. on p. 2633 ff. details recent dual HBD catalyst design elements and their effect on HBD catalyst performance.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
    1. Graphical Abstract: Eur. J. Org. Chem. 13/2014 (pages 2619–2625)

      Article first published online: 22 APR 2014 | DOI: 10.1002/ejoc.201490035

  3. News

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

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

      Design Strategies for Enhanced Hydrogen-Bond Donor Catalysts (pages 2633–2646)

      Tyler J. Auvil, Andrew G. Schafer and Anita E. Mattson

      Article first published online: 21 MAR 2014 | DOI: 10.1002/ejoc.201400035

      Thumbnail image of graphical abstract

      Since initial reports of organocatalysis through hydrogen bonding interactions, a number of strategies have emerged to allow access to enhanced hydrogen-bond donor (HBD) organocatalysts. These strategies range from augmentation of existing HBDs to the design and synthesis of new HBD catalysts. The effects of recent dual HBD designs on catalyst performance are described.

    2. β-Lactams

      Progress in Asymmetric Organocatalytic Synthesis of β-Lactams (pages 2647–2657)

      Plato A. Magriotis

      Article first published online: 28 JAN 2014 | DOI: 10.1002/ejoc.201301720

      Thumbnail image of graphical abstract

      The importance of β-lactams and asymmetric organocatalysis is first discussed, followed by the initial asymmetric syntheses of β-lactams with the aid of chirally modified transition-metal catalysts. Progress in organocatalyzed enantioselective Staudinger syntheses of β-lactams since 2001, including kinetic resolution of β-lactams and indirect asymmetric syntheses of β-lactams, is then reviewed.

  5. Short Communications

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

      A Model Study toward the Concise Synthesis of Bromotyrosine-Derived Spiroisoxazoline Natural Products and Analogous Core Structures (pages 2659–2663)

      Prasanta Das, Edward J. Valente and Ashton T. Hamme II

      Article first published online: 13 MAR 2014 | DOI: 10.1002/ejoc.201400009

      Thumbnail image of graphical abstract

      The efficient syntheses of functionalized spiroisoxazolines that closely resemble bromotyrosine-derived spiroisoxazoline natural product core structures are described. This described strategy could serve as an efficient alternative to previously developed approaches that involve aromatic ring oxidation as the essential step to synthesize this class of natural products.

    2. Secondary Structure Mimetics

      Stereoselective Synthesis of Proline-Derived Dipeptide Scaffolds (ProM-3 and ProM-7) Rigidified in a PPII Helix Conformation (pages 2664–2667)

      Cédric Reuter, Margarethe Kleczka, Sarah de Mazancourt, Jörg-Martin Neudörfl, Ronald Kühne and Hans-Günther Schmalz

      Article first published online: 25 MAR 2014 | DOI: 10.1002/ejoc.201301875

      Thumbnail image of graphical abstract

      Starting from amino acid building blocks with an olefin side chain, the diastereomeric scaffolds ProM-3 and ProM-7 are synthesized through peptide coupling and ring-closing metathesis. The conformationally defined dipeptide analogs are of interest as building blocks for the synthesis of modular PPII helix secondary structure mimetics as tailored inhibitors of protein–protein interactions.

    3. Hydration Reactions

      Gold(I)-Catalyzed Hydration of Alkynylphosphonates: Efficient Access to β-Ketophosphonates (pages 2668–2671)

      Longyong Xie, Rui Yuan, Ruijia Wang, Zhihong Peng, Jiannan Xiang and Weimin He

      Article first published online: 17 MAR 2014 | DOI: 10.1002/ejoc.201400066

      Thumbnail image of graphical abstract

      An efficient and mild gold-catalyzed hydration process for the regioselective synthesis of β-ketophosphonates directly from alkynylphosphonates is described. Twenty-two examples with yields of 85–97 % are reported. Different substituents including substituted aryl, alkyl, chloro, ester, sulfonoxyl, and phthalimide groups are tolerated; XPhos = 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, Tf = trifluoromethylsulfonyl.

    4. Ring Opening of Cyclopropenone

      Phosphane- and Amine-Catalyzed Ring-Opening Reactions of Cyclopropenones with Isatin Derivatives: Synthesis of Carboxylated 1H-Indoles and Multisubstituted 2H-Pyran-2-ones (pages 2672–2676)

      Wen-Tao Zhao, Xiang-Ying Tang and Min Shi

      Article first published online: 12 MAR 2014 | DOI: 10.1002/ejoc.201400077

      Thumbnail image of graphical abstract

      Phosphane- and amine-catalyzed ring-opening reactions of cyclopropenones with isatin derivatives are developed. These reactions offer a facile synthetic method to construct carboxylated 1H-indoles and multisubstituted 2H-pyran-2-ones; Boc = tert-butoxycarbonyl, DABCO = 1,4-diazabicyclo[2.2.2]octane.

    5. Asymmetric Organocatalysis

      Regio- and Enantioselective Organocascade Michael–Michael Reactions: Construction of Chiral Trisubstituted Indanes (pages 2677–2681)

      Ning Li, Guo-Gui Liu, Jian Chen, Feng-Feng Pan, Bing Wu and Xing-Wang Wang

      Article first published online: 27 MAR 2014 | DOI: 10.1002/ejoc.201301860

      Thumbnail image of graphical abstract

      An organocatalytic regio- and enantioselective cascade conjugate addition reaction is developed for the construction of enantiomerically enriched 1,2,3-trisubstituted indanes. The resulting indane derivatives can be readily converted into optically active (1-indanylmethyl)amine and tetrahydroindeno[2,1-b]pyrrole derivatives. Boc = tert-butoxycarbonyl.

    6. Domino Reactions

      Copper-Catalyzed Domino Reaction Involving C–C Bond Cleavage To Construct 2-Aryl Quinazolinones (pages 2682–2685)

      Li-Xia Wang, Jun-Feng Xiang and Ya-Lin Tang

      Article first published online: 25 MAR 2014 | DOI: 10.1002/ejoc.201400108

      Thumbnail image of graphical abstract

      A copper-catalyzed approach for the synthesis of 2-aryl-quinazolinones through a domino reaction involving C–C bond cleavage is described. This transformation offers an alternative method to prepare medically important quinazolinone derivatives and a new strategy for C–C bond cleavage.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
    1. Tunable Anion Binding

      Synthesis of 1,2,3-Triazole-4-carboxamide-Containing Foldamers for Sulfate Recognition (pages 2687–2693)

      Li Cao, Runsheng Jiang, Yulan Zhu, Xinlong Wang, Yongjun Li and Yuliang Li

      Article first published online: 27 FEB 2014 | DOI: 10.1002/ejoc.201301838

      Thumbnail image of graphical abstract

      A series of triazolecarboxamide-containing foldamers were synthesized. By increasing the numbers of triazolecarboxamide units and modification of the terminal benzene ring, the binding stoichiometry and binding affinity can be controlled.

    2. Helical Organocatalysts

      Synthesis, Characterisation, and Organocatalytic Activity of Chiral Tetrathiahelicene Diphosphine Oxides (pages 2694–2702)

      Silvia Cauteruccio, Davide Dova, Maurizio Benaglia, Andrea Genoni, Manuel Orlandi and Emanuela Licandro

      Article first published online: 6 MAR 2014 | DOI: 10.1002/ejoc.201301912

      Thumbnail image of graphical abstract

      A novel class of tetrathia[7]helicene-based diphosphine oxides has been synthesised, and their catalytic behaviour as chiral helical phosphorus Lewis bases has been preliminary investigated in organocatalytic reactions.

    3. Non-natural Peptides

      δ-Peptides from RuAAC-Derived 1,5-Disubstituted Triazole Units (pages 2703–2713)

      Johan R. Johansson, Elin Hermansson, Bengt Nordén, Nina Kann and Tamás Beke-Somfai

      Article first published online: 14 FEB 2014 | DOI: 10.1002/ejoc.201400018

      Thumbnail image of graphical abstract

      A new set of non-natural peptides composed of 1,5-disubstituted 1,2,3-triazole amino acids is presented. These peptides benefit from: a) modular synthesis of the monomers, allowing variation of the side chains; b) increased solubility of the oligomers in water, irrespective of peptide length; c) flexibility of the backbone allowing these foldamers to adopt several conformations.

    4. Peptidomimetics

      Structural Prerequisites for Receptor Binding of Helicokinin I, a Diuretic Insect Neuropeptide from Helicoverpa zea (pages 2714–2725)

      Chien Tran Van, Tino Zdobinsky, Guiscard Seebohm, Dirk Nennstiel, Oliver Zerbe and Jürgen Scherkenbeck

      Article first published online: 26 FEB 2014 | DOI: 10.1002/ejoc.201301773

      Thumbnail image of graphical abstract

      A delicate balance of rigidity and flexibility makes the difference between activity and inactivity. Detailed conformational studies of analogues of the diuretic insect-neuropeptide helicokinin I containing diverse cyclic scaffolds with different flexibility and orientation of the N- and C-termini provide a better understanding of the structural requirements for receptor binding.

    5. [4+3] Cycloaddition

      Use of the p-Tolylsulfinyl Group as a Chiral Inductor in Stereoselective [4+3] Cycloaddition Reactions: Preparation of Enantiopure Polysubstituted 8-Oxabicyclo[3.2.1]oct-6-en-3-one Systems Having up to Five Stereocenters (pages 2726–2746)

      Ángel M. Montaña, Pedro M. Grima, Consuelo Batalla, Francisca Sanz and Gabriele Kociok-Köhn

      Article first published online: 25 FEB 2014 | DOI: 10.1002/ejoc.201301814

      Thumbnail image of graphical abstract

      The use of the p-tolylsulfinyl group as a chiral inductor in stereoselective [4+3] cycloadditions has led to the preparation of enantiopure polysubstituted 8-oxabicyclo[3.2.1]oct-6-en-3-ones with up to five stereocenters in yields of 50–80 %. By using appropriate substituents on the furan ring, 100:0 cis-trans, 100:0 endo-exo, and up to 100 % π-facial diastereoselectivities were achieved.

    6. Orthophosphate Recognition

      Guanidinium-Based Artificial Receptors for Binding Orthophosphate in Aqueous Solution (pages 2747–2753)

      Evgeny A. Kataev, Christoph Müller, Grigory V. Kolesnikov and Victor N. Khrustalev

      Article first published online: 27 FEB 2014 | DOI: 10.1002/ejoc.201301867

      Thumbnail image of graphical abstract

      Selective recognition of orthophosphate in aqueous solution was achieved by receptors based on guanidinium and pyrrole binding sites. The structure of pyrrole-containing binding sites has great influence on the selectivity of receptors for orthophosphate. The receptor with bulky substituents in the meso-position of the dipyrrolylmethane core demonstrated the highest selectivity for orthophosphate

    7. Nitrogen Heterocycles

      Iron(III)-Catalyzed Denitration Reaction: One-Pot Three-Component Synthesis of Imidazo[1,2-a]pyridine Derivatives (pages 2754–2763)

      Hao Yan, Yuling Wang, Congming Pan, Hao Zhang, Sizhuo Yang, Xiaoyu Ren, Jian Li and Guosheng Huang

      Article first published online: 11 MAR 2014 | DOI: 10.1002/ejoc.201301658

      Thumbnail image of graphical abstract

      An iron(III)-catalyzed one-pot three-component cross-coupling nitration reaction of 2-aminopyridines, aldehydes, and nitroalkane, leading to the straightforward formation of imidazo[1,2-a]pyridine derivatives has been reported. In this procedure, the starting materials are commercially available. The system shows good functional-group tolerance and proceeds smoothly in moderate to good yields.

    8. Triplet Aromaticity

      Evaluation of Triplet Aromaticity by the Indene–Isoindene Isomerization Stabilization Energy Method (pages 2764–2769)

      Ke An and Jun Zhu

      Article first published online: 5 MAR 2014 | DOI: 10.1002/ejoc.201301810

      Thumbnail image of graphical abstract

      Triplet aromaticity has been evaluated by applying the indene–isoindene isomerization stabilization energy (ISE) method. The reliability of this approach can be demonstrated by the strong correlation of ISE values with NICS(1)zz as well as the previous methyl–methylene ISE values. Our results verify Baird's rule: that triplet annulenes with 4n π-electrons are aromatic.

    9. Nucleoside Analogues

      Synthesis of Purine Nucleosides from D-Glucuronic Acid Derivatives and Evaluation of Their Cholinesterase-Inhibitory Activities (pages 2770–2779)

      Nuno M. Xavier, Stefan Schwarz, Pedro D. Vaz, René Csuk and Amélia P. Rauter

      Article first published online: 6 MAR 2014 | DOI: 10.1002/ejoc.201301913

      Thumbnail image of graphical abstract

      The synthesis of furanosyl and pyranosyl N9 and N7 purine nucleosides containing glucofuranurono-6,3-lactone, N-benzylglucuronamide, and glucuronic acid moieties is reported. Glucuronolactones were used as glycosyl donors or converted into suitable 1-O-acetyl derivatives for purine glycosylation. Some nucleosides showed moderate and selective inhibition of acetylcholinesterase.

    10. Trisubstituted 2,5-Diketopiperazines

      Asymmetric Synthesis of 3,4,6-Trisubstituted 2,5-Diketopiperazines by Using Dynamic Kinetic Resolution of α-Bromo Tertiary Acetamides (pages 2780–2789)

      Jinho Baek, Seock Yong Kang, Chan Im and Yong Sun Park

      Article first published online: 6 MAR 2014 | DOI: 10.1002/ejoc.201301936

      Thumbnail image of graphical abstract

      A new asymmetric synthetic route to 3,4,6-trisubstituted 2,5-diketopiperazines has been developed by using a nucleophilic substitution reaction of L-amino-acid-derived α-bromo tertiary acetamides with p-anisidine followed by a deprotection–cyclization process.

    11. C–H Activation

      A Commercially Available Tantalum Catalyst for the Highly Regioselective Intermolecular Hydroaminoalkylation of Styrenes (pages 2790–2797)

      Jaika Dörfler and Sven Doye

      Article first published online: 4 MAR 2014 | DOI: 10.1002/ejoc.201400082

      Thumbnail image of graphical abstract

      Highly regioselective intermolecular hydroaminoalkylation reactions of styrenes are achieved in the presence of the commercially available homoleptic catalyst [Ta(NMe2)5]. The process activates the α-C–H bonds of N-methylanilines and 1,2,3,4-tetrahydroquinoline and gives access to the corresponding branched hydroaminoalkylation products in good-to-excellent yields.

    12. Tröger's Bases

      Synthesis of Unsymmetrical Tröger's Bases Bearing Groups Sensitive to Reduction (pages 2798–2805)

      Martin Havlík, Bohumil Dolenský, Milan Jakubek and Vladimír Král

      Article first published online: 10 MAR 2014 | DOI: 10.1002/ejoc.201301517

      Thumbnail image of graphical abstract

      We report an efficient synthetic protocol for the preparation of Tröger's base derivatives bearing functional groups sensitive to reduction conditions. Twelve unsymmetrical derivatives were prepared in high overall yields using this protocol.

    13. C–H Functionalization/Cyclization

      Copper- and Palladium-Cocatalyzed Intramolecular C–H Functionalization/C–N Bond Formation: A Route to the Synthesis of Indoloisoquinoline Derivatives (pages 2806–2812)

      Somjit Hazra, Biplab Mondal, Habibur Rahaman and Brindaban Roy

      Article first published online: 28 FEB 2014 | DOI: 10.1002/ejoc.201301699

      Thumbnail image of graphical abstract

      A new approach to the synthesis of indoloisoquinoline derivatives is described. The activation of the indole C2–H bond is accomplished here by using a Pd(OAc)2 and Cu(OTf)2 bi-catalytic system. In this reaction aldoximes are converted into the corresponding isoquinolines in open atmosphere under mild reaction condition.

SEARCH

SEARCH BY CITATION