European Journal of Organic Chemistry

Cover image for Vol. 2012 Issue 21

July 2012

Volume 2012, Issue 21

Pages 3875–4070

  1. Cover Picture

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

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Graphical Abstract: Eur. J. Org. Chem. 21/2012 (pages 3875–3880)

      Article first published online: 11 JUL 2012 | DOI: 10.1002/ejoc.201290056

  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. Perylenequinone Natural Products

      Perylenequinones: Isolation, Synthesis, and Biological Activity (pages 3887–3904)

      Carol A. Mulrooney, Erin M. O'Brien, Barbara J. Morgan and Marisa C. Kozlowski

      Article first published online: 23 MAY 2012 | DOI: 10.1002/ejoc.201200184

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      Perylenequinones are a class of natural products characterized by a pentacyclic conjugated chromophore giving rise to photoactivity. Their structural complexity and light-induced biological activity have resulted in extensive study of these compounds. This review focuses on recent isolates in this class, total synthesis work, semisynthetic analogs, and biological activity studies.

  5. Short Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Luminescent Ln(III) Complexes

      Synthesis of 2,6-Bis(oxazolyl)pyridine Ligands for Luminescent LnIII Complexes (pages 3905–3910)

      Goreti Pereira, Miguel F. Ferreira, Elisabete M. S. Castanheira, José A. Martins and Paula M. T. Ferreira

      Article first published online: 18 JUN 2012 | DOI: 10.1002/ejoc.201200177

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      New bis(oxazolyl)pyridine ligands for LnIII ions were prepared by using an expeditious methodology from threonine and dipicolinic chloride. Photophysical studies of the EuIII and TbIII complexes with this ligand showed that the 2,6-bis(oxazolyl)pyridine moiety acts as an effective sensitizer for lanthanide luminescence and indicate the formation of 3:1 complexes [Ln{bis(oxazole)pyridine}3]3+.

    2. Reaction Mechanisms

      Mechanistic Insight into the Nickel-Catalyzed Intermolecular [3+2+2] Cocyclization of Ethyl Cyclopropylideneacetate with Alkynes: DFT Calculations (pages 3911–3915)

      Yanhong An, Caihong Cheng, Ben Pan and Zhihong Wang

      Article first published online: 13 JUN 2012 | DOI: 10.1002/ejoc.201200363

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      DFT investigations revealed that the mechanism of the nickel-catalyzed [3+2+2] cocyclization of ethyl cyclopropylideneacetate and alkynes occurs through a sequence of ring-opening and ring-closing reactions with C–C bond formation as the rate-determining step.

    3. Domino Reaction

      Versatile Domino Rearrangement of Diphenylhomobenzoquinone Epoxides Induced by CF3SO3H (pages 3916–3919)

      Haruyasu Asahara, Satoshi Matsui, Yoshiro Masuda, Naohiko Ikuma and Takumi Oshima

      Article first published online: 14 JUN 2012 | DOI: 10.1002/ejoc.201200455

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      Acid-catalyzed reaction of various 5-alkyl-substituted diphenylhomobenzoquinone epoxides provided various products through novel cationic domino rearrangements and decarbonylation depending on the acid (BF3/MeSO3H/TfSO3H) and the alkyl substituents (R = Me/iPr/tBu).

    4. Azasugars

      Double Reductive Amination and Selective Strecker Reaction of a D-Lyxaric Aldehyde: Synthesis of Diversely Functionalized 3,4,5-Trihydroxypiperidines (pages 3920–3924)

      Camilla Matassini, Stefania Mirabella, Andrea Goti and Francesca Cardona

      Article first published online: 15 JUN 2012 | DOI: 10.1002/ejoc.201200587

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      The synthesis of natural 3,4,5-trihydroxypiperidines and non-natural N-alkylated derivatives from a dialdehyde possessing the D-lyxo configuration is presented herein. The highly regio- and diastereoselective Strecker reaction on the same key aldehyde allowed access to important precursors of pipecolic acids and diaminopiperidine compounds.

    5. Reductive Esterification

      Straightforward Reductive Esterification of Carbonyl Compounds with Carboxylic Acids through Tosylhydrazone Intermediates (pages 3925–3928)

      Angel-Humberto García-Muñoz, María Tomás-Gamasa, M. Carmen Pérez-Aguilar, Erick Cuevas-Yañez and Carlos Valdés

      Article first published online: 20 JUN 2012 | DOI: 10.1002/ejoc.201200647

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      Esters can be readily obtained by reaction between the tosylhydrazones of aldehydes or ketones and carboxylic acids through an operationally very simple procedure that requires only the presence of K2CO3 as base.

  6. Full Papers

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

      Straightforward Synthesis of Poly(dimethylsiloxane) Phases with Immobilized (1R)-3-(Perfluoroalkanoyl)camphorate Metal Complexes and Their Application in Enantioselective Complexation Gas Chromatography (pages 3929–3945)

      Markus J. Spallek, Golo Storch and Oliver Trapp

      Article first published online: 3 MAY 2012 | DOI: 10.1002/ejoc.201200075

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      A novel synthetic approach to camphor-based chemically bonded Chirasil-Metal-OC3 [Ni, Eu, La, V(O)] stationary phases and thir application in enantioselective complexation GC is presented. Immobilization and metal incorporation was studied with a range of selector concentrations using NMR and IR spectroscopy. Overall, 29 compounds with different functionalities were separated with α-values up to 1.66.

    2. Conformational Control of Peptides

      The Synthesis and Characterization of a Pentafluorosulfanylated Peptide (pages 3946–3954)

      Dong Sung Lim, Jin-Hong Lin and John T. Welch

      Article first published online: 6 JUN 2012 | DOI: 10.1002/ejoc.201200327

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      The design and synthesis of pentafluorosulfanyl-containing heptad amino acid sequence was described. The investigation of the peptide conformation shows that the one of the diastereomers assumed a very tight coiled conformation in [D6]DMSO where both pentafluorosulfanyl groups assumed a synclinal relationship. The propensity of the protected heptapeptide to form such a tight coil and of the pentafluorosulfanyl groups to align so uniformly is suggestive of the utility of pentafluorosulfanylated amino acids in promoting conformational control.

    3. Calixarenes

      Inherently Chiral Cyano-Substituted Resorcin[4]arene: A Promising Starting Point for Further Functionalization (pages 3955–3961)

      Sebastian Wiegmann, Beate Neumann, Hans-Georg Stammler and Jochen Mattay

      Article first published online: 12 JUN 2012 | DOI: 10.1002/ejoc.201200507

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      Inherently chiral cyanoresorcin[4]arene has been prepared by palladium-catalyzed cyanation of the corresponding triflate. Further conversions led to, for example, the tertiary alcohol. X-ray structure analysis revealed a strong twist of the macrocycle.

    4. Supramolecular Chemistry

      Complexation of p-Sulfonatocalixarenes with Local Anaesthetics Guests: Binding Structures, Stabilities, and Thermodynamic Origins (pages 3962–3971)

      Qian Li, Dong-Sheng Guo, Hai Qian and Yu Liu

      Article first published online: 12 JUN 2012 | DOI: 10.1002/ejoc.201200515

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      The intermolecular complexation of three water-soluble p-sulfonatocalixarenes with five local anaesthetics (LA) guests were systematically investigated with respect to their binding geometries and thermodynamic origins. The appreciable host selectivity showed that p-sulfonatocalix[4]arene presents the highest complex constant to LA guests, more than ten times larger than p-sulfonatothiacalix[4]arene.

    5. Buchwald–Hartwig Amination

      Buchwald–Hartwig Amination of (Hetero)aryl Chlorides by Employing Mor-DalPhos under Aqueous and Solvent-Free Conditions (pages 3972–3977)

      Bennett J. Tardiff and Mark Stradiotto

      Article first published online: 6 JUN 2012 | DOI: 10.1002/ejoc.201200510

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      We report on the use of [Pd(cinnamyl)Cl]2/Mor-DalPhos in the Buchwald–Hartwig amination of (hetero)aryl chlorides with primary or secondary amines under aqueous or solvent-free conditions (52examples).

    6. Structure Elucidation by Synthesis

      Total Syntheses of the Gregatins A–D and Aspertetronin A: Structure Revisions of These Compounds and of Aspertetronin B, Together with Plausible Structure Revisions of Gregatin E, Cyclogregatin, Graminin A, the Penicilliols A and B, and the Huaspenones A and B (pages 3978–4017)

      Heike Burghart-Stoll and Reinhard Brückner

      Article first published online: 12 JUN 2012 | DOI: 10.1002/ejoc.201200207

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      Our recent discovery of the correct structure of gregatin B was an incentive for developing straightforward and (stereo)structure-revising syntheses of the gregatins A–D from L-lactic acid. An unprecedented α-acylation of a γ-hydroxy-β-oxo ester allowed furanone formation through a nucleophilic vinylic substitution.

    7. Stable Carbenes

      Stable N-Heterocyclic Carbenes: N-Alkyl-N′-phosphanylbenzimidazol-2-ylidenes (pages 4018–4033)

      Anatoliy P. Marchenko, Heorgiy N. Koidan, Anastasiia N. Hurieva, Igor I. Pervak, Svitlana V. Shishkina, Oleg V. Shishkin and Aleksandr N. Kostyuk

      Article first published online: 12 JUN 2012 | DOI: 10.1002/ejoc.201200282

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      A number of approaches to N-alkyl-N′-phosphanylbenzimidazolium salts were developed. These salts were used for the preparation of stable N-alkyl-N′-phosphanylbenzimidazol-2-ylidenes. Chemical properties of both the salts and the carbenes with O-, N-, and C-nucleophiles were studied. Both salts and the carbenes arepotential ligands for polynuclear complexes.

    8. Cross-Coupling

      Application of LB-Phos·HBF4 in the Suzuki Coupling Reaction of 2-Bromoalken-3-ols with Alkylboronic Acids (pages 4034–4041)

      Binjie Guo, Chunling Fu and Shengming Ma

      Article first published online: 6 JUN 2012 | DOI: 10.1002/ejoc.201200350

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      LB-Phos·HBF4 was used in the Suzuki coupling reaction of 2-bromoalken-3-ols with alkylboronic acids to afford the coupling products in moderate to good yields. Substituents such as benzyl, phenyl, allyl, and alkyl are tolerated at the 1- and 3-positions of the 2-bromoalken-3-ols.

    9. Asymmetric Catalysis

      Asymmetric Friedel–Crafts Alkylation of Indoles with Nitrodienes and 2-Propargyloxy-β-nitrostyrenes Catalyzed by Diphenylamine-Linked Bis(oxazoline)–Zn­(OTf)2 Complexes (pages 4042–4051)

      Jiahuan Peng and Da-Ming Du

      Article first published online: 6 JUN 2012 | DOI: 10.1002/ejoc.201200382

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      The catalytic asymmetric Friedel–Crafts reaction of indoles with nitrodienes and 2-propargyloxy-β-nitrostyrenes was investigated with diphenylamine-linked bis(oxazoline)–Zn(OTf)2 complexes. Moderate to good enantioselectivities were obtained with both kinds of substrate (up to 89 % ee for nitrodienes and up to 93 % ee for β-nitrostyrene derivatives).

    10. Polycycles and Amino Acids

      Diversity Oriented Approach to Polycyclic Compounds through the Diels–Alder Reaction and the Suzuki Coupling (pages 4052–4062)

      Sambasivarao Kotha, Shilpi Misra and Venu Srinivas

      Article first published online: 12 JUN 2012 | DOI: 10.1002/ejoc.201200484

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      Small “drug like” molecules are obtained by using alkylation, Diels–Alder reaction, and Suzuki–Miyaura cross-coupling as key steps. This methodology allows a wide range of molecules to be assembled using simple scaffolds such as indanes, tetralins, and tetrahydroisoquinolines, which can enhance the chemical space for potential therapeutic molecules.

    11. Artificial Enzymes

      Synthesis of Cyclodextrins with Carboxylic Acids at the Secondary Rim and an Evaluation of Their Properties as Chemzymes for Glycoside Hydrolysis (pages 4063–4070)

      You Zhou, Emil Lindbäck, Lavinia G. Marinescu, Christian Marcus Pedersen and Mikael Bols

      Article first published online: 6 JUN 2012 | DOI: 10.1002/ejoc.201200404

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      Are carboxymethylated cyclodextrins glycosidase mimics? This question was investigated for a range of carboxymethylated cyclodextrins with and without O-methyl groups.

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