European Journal of Organic Chemistry

Cover image for Vol. 2008 Issue 31

November 2008

Volume 2008, Issue 31

Pages 5191–5345

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Synthesis of Chiral Amines Using α-Amino Aldehydes (Eur. J. Org. Chem. 31/2008) (page 5191)

      Ryan Hili, Sivaraj Baktharaman and Andrei K. Yudin

      Article first published online: 16 OCT 2008 | DOI: 10.1002/ejoc.200890084

  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. 31/2008 (pages 5191–5196)

      Article first published online: 16 OCT 2008 | DOI: 10.1002/ejoc.200890086

  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. Amino Aldehydes

      Synthesis of Chiral Amines Using α-Amino Aldehydes (pages 5201–5213)

      Ryan Hili, Sivaraj Baktharaman and Andrei K. Yudin

      Article first published online: 10 SEP 2008 | DOI: 10.1002/ejoc.200800604

      Thumbnail image of graphical abstract

      If one were to rank chemical reagents on the basis of their “synthetic content”, loosely defined as the density of functional groups per arbitrary unit of molecular space, the α-amino aldehydes will find themselves close to the very top of that list. The presence of synthetically ubiquitous amine and aldehyde functionalities predisposes α-amino aldehydes towards highly convergent bond-forming operations. Such juxtaposition does not come without a price: incompatibility of these functional groups calls for protecting groups. We discuss challenges and recently identified opportunities in this field.

  5. Short Communications

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

      Regioselective Domino Metathesis of 7-Oxanorbornenes and Its Application to the Synthesis of Biologically Active Glutamate Analogues (pages 5215–5220)

      Minoru Ikoma, Masato Oikawa, Martin B. Gill, Geoffrey T. Swanson, Ryuichi Sakai, Keiko Shimamoto and Makoto Sasaki

      Article first published online: 22 SEP 2008 | DOI: 10.1002/ejoc.200800704

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      Twelve artificial glutamate analogues inspired by natural products were efficiently synthesized by employing a regioselectivedomino metathesis reaction of 7-oxanorbornenes as the key step. One analogue was found to exhibit unique hypoactivity.

    2. Stereogenic Boron

      Boron-Based Diastereomerism and Enantiomerism in Imine Complexes – Determination of the Absolute Configuration at Boron by CD Spectroscopy (pages 5221–5225)

      Manfred Braun, Sebastian Schlecht, Marco Engelmann, Walter Frank and Stefan Grimme

      Article first published online: 17 SEP 2008 | DOI: 10.1002/ejoc.200800787

      Thumbnail image of graphical abstract

      Boron turns out to be a stable stereogenic center in imine complexes of aryl and alkyl boronates. Calculated and measured CDspectra permit to assign the absolute configuration to boron in the first enantiomeric boronate-imine complexes.

    3. Nucleophilic Trifluoromethylation

      Nucleophilic Trifluoromethylation of Imines under Acidic Conditions (pages 5226–5230)

      Vitalij V. Levin, Alexander D. Dilman, Pavel A. Belyakov, Marina I. Struchkova and Vladimir A. Tartakovsky

      Article first published online: 25 SEP 2008 | DOI: 10.1002/ejoc.200800820

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      The first example of nucleophilic trifluoromethylation by using Me3SiCF3 proceeding in the presence of strong protic acids isdescribed. The presented methodologybroadens significantly the scope of the trifluoromethylation of the C=N bond and offers a new selectivity profile for the application of fluorinated silicon reagents.

  6. Full Papers

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

      New Fluorescent Calix Crown Ethers, Part II: Synthesis and Complex Formation in Solution and the Solid State (pages 5231–5238)

      Ion Stoll, Ralf Brodbeck, Sebastian Wiegmann, Jens Eberhard, Silke Kerruth, Beate Neumann, Hans-Georg Stammler and Jochen Mattay

      Article first published online: 22 SEP 2008 | DOI: 10.1002/ejoc.200800569

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      A new resorc[4]arene-based host molecule was synthesized by attaching a 1-aza-15-crown-5 ether to a cavitand. The association constants for alkali-metal complexes in solution were determined by means of fluorescence titrations, indicating an enhanced selectivity for sodium cations. Selected equilibrium structures of the formed complexes were examined by Kohn–Sham DFT calculations to give a detailed understanding of the interplay between the two involved building blocks.

    2. Fluorescent Sensor for Water

      A New Class of Fluorescent Dye for Sensing Water in Organic Solvents by Photo-Induced Electron Transfer – A (Phenylamino)naphtho[1,2-d]oxazol-2-yl-Type Fluorophore with both Proton-Binding and Proton-Donating Sites (pages 5239–5243)

      Yousuke Ooyama, Haruka Egawa and Katsuhira Yoshida

      Article first published online: 22 SEP 2008 | DOI: 10.1002/ejoc.200800606

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      A new class of fluorescent dye for sensing water in organic solvents by photo-induced electron transfer (PET), based on a (phenylamino)naphtho[1,2-d]oxazol-2-yl-type fluorophore with both proton binding and proton donating sites, has been designed and developed.

    3. NHC-Pyridine Complexes

      Green Catalysts: Solid-Phase Peptide Carbene Ligands in Aqueous Transition-Metal Catalysis (pages 5244–5253)

      Kasper Worm-Leonhard and Morten Meldal

      Article first published online: 25 SEP 2008 | DOI: 10.1002/ejoc.200800633

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      Peptide-based NHC-pyridine ligands and their palladium complexes were synthesized on solid support and characterized by NMR and mass spectrometry. The supported ligands were complexed to palladium by treatment with BEMP and PdCl2COD. Successful catalytic applications were demonstrated in Sonogashira and Suzuki cross-coupling reactions performed in organic solvent or water.

    4. Drug Discovery

      Domino Heck–Aza-Michael Reactions: A One-Pot, Sequential Three-Component Approach to 1,1-Dioxido-1,2-benzisothiazoline-3-acetic Acid (pages 5254–5262)

      Alan Rolfe, Kyle Young and Paul R. Hanson

      Article first published online: 22 SEP 2008 | DOI: 10.1002/ejoc.200800651

      Thumbnail image of graphical abstract

      The development of a new method for the synthesis of 1,1-dioxido-1,2-benzisothiazoline-3-acetic acid by a domino process is reported. Ultimately, this method has been expanded to a one-pot, sequential three-component protocol to generate diverse benzofused γ-sultams from a range of commercially available α-bromobenzenesulfonyl chlorides, amines and Michael acceptors.

    5. γ-Amino Acids

      Enzymatic Method for the Synthesis of Blockbuster Drug Intermediates – Synthesis of Five-Membered Cyclic γ-Amino Acid and γ-Lactam Enantiomers (pages 5263–5268)

      Enikő Forró and Ferenc Fülöp

      Article first published online: 30 SEP 2008 | DOI: 10.1002/ejoc.200800723

      Thumbnail image of graphical abstract

      A very efficient enzymatic method is reported for the synthesis of cyclic γ-lactam and γ-amino acid enantiomers through the CAL-B-catalysed enantioselective (E > 200) hydrolysis of the corresponding N-Boc protected and unprotected racemic γ-lactams with H2O in iPr2O.

    6. Dynamic Kinetic Resolution

      Directed (R)- or (S)-Selective Dynamic Kinetic Enzymatic Hydrolysis of 1,2,3,4-Tetrahydroisoquinoline-1-carboxylic Esters (pages 5269–5276)

      Tihamér A. Paál, Arto Liljeblad, Liisa T. Kanerva, Enikő Forró and Ferenc Fülöp

      Article first published online: 30 SEP 2008 | DOI: 10.1002/ejoc.200800789

      Thumbnail image of graphical abstract

      The first synthesis of both enantiomers of6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid was accomplished through dynamic kinetic resolution.

    7. Keto Phosphonates

      Alcoholysis of Phosphaisocoumarins and Synthesis of 2-(2-Oxoalkyl)phenylphosphonates (pages 5277–5282)

      Ai-Yun Peng, Yu-Juan Guo, Zhi-Hai Ke and Shizheng Zhu

      Article first published online: 25 SEP 2008 | DOI: 10.1002/ejoc.200800616

      Thumbnail image of graphical abstract

      Alcoholysis of phosphaisocoumarins to 2-(2-oxoalkyl)phenylphosphonates was extensively studied. The obtained novel keto phosphonates could also be synthesized directly by the hydration of 2-(1-alkynyl)phenylphosphonates; these compounds showed medium inhibitory activity towards α-chymotrypsin.

    8. Natural Products

      Grecoketides A and B: New Naphthoquinones from Streptomyces sp. Acta 1362 (pages 5283–5288)

      Thomas Paululat, Efstathios A. Katsifas, Amalia D. Karagouni and Hans-Peter Fiedler

      Article first published online: 17 SEP 2008 | DOI: 10.1002/ejoc.200800676

      Thumbnail image of graphical abstract

      During HPLC/diode-array screening for new secondary metabolites, two new compounds were produced by Streptomyces sp. Acta 1362 and were named as grecoketides A and B. The fermentation, isolation, structure elucidation and biosynthetic studies of these two compounds are described.

    9. Polyhydroxylated Indolizidines

      Synthesis and Glycosidase Inhibitory Study of New Polyhydroxylated Indolizidines (pages 5289–5300)

      Delphine Baumann, Khalil Bennis, Isabelle Ripoche, Vincent Théry and Yves Troin

      Article first published online: 30 SEP 2008 | DOI: 10.1002/ejoc.200800684

      Thumbnail image of graphical abstract

      The preparation of two polyhydroxylated indolizidines, (–)-12 and (–)-27, is reported. The piperidine ring was formed by an intramolecular Mannich-type reaction. Theinhibitory properties of the two synthesized indolizidines were evaluated against a variety of commercial glycosidases.

    10. Stable Carbocation

      Synthesis, Stability, and Crystal Structure of an Azulenium Cation Containing an Adamantyl Group (pages 5301–5307)

      Mitsunori Oda, Nobue Nakajima, Nguyen Chung Thanh, Kazuhiro Kitahara, Ryuta Miyatake and Shigeyasu Kuroda

      Article first published online: 22 SEP 2008 | DOI: 10.1002/ejoc.200800700

      Thumbnail image of graphical abstract

      The pKR+ value of the title cation was found to be 9.8, which is less than that expected by inductive stabilization from the numbers of carbons at the 1-position. TheX-ray crystal structure of the title cation (ClO4 salt) reveals CH–O interactions and deformation of the azulenyl ion part.

    11. “Clickable” Peptides

      Nα-Fmoc-Protected ω-Azido- and ω-Alkynyl-L-amino Acids as Building Blocks for the Synthesis of “Clickable” Peptides (pages 5308–5314)

      Alexandra Le Chevalier Isaad, Francesca Barbetti, Paolo Rovero, Anna Maria D'Ursi, Mario Chelli, Michael Chorev and Anna Maria Papini

      Article first published online: 25 SEP 2008 | DOI: 10.1002/ejoc.200800717

      Thumbnail image of graphical abstract

      Synthesis of Nα-Fmoc-ω-azido- and Nα-Fmoc-ω-yne-L-amino acids as buildingblocks for pseudopeptide precursors of inter- and intramolecular click reactions.

    12. Organocatalysis

      Catalytic Enantioselective α-Oxysulfonylation of Ketones Mediated by Iodoarenes (pages 5315–5328)

      Sabine M. Altermann, Robert D. Richardson, T. Keri Page, Ruth K. Schmidt, Edward Holland, Umal Mohammed, Shauna M. Paradine, Andrew N. French, Christine Richter, A. Masih Bahar, Bernhard Witulski and Thomas Wirth

      Article first published online: 16 SEP 2008 | DOI: 10.1002/ejoc.200800741

      Thumbnail image of graphical abstract

      The α-oxysulfonylation of ketones catalysed by enantioenriched iodoarenes using mCPBA as stoichiometric oxidant is reported to give useful synthetic intermediates in good yield and modest enantioselectivity.

    13. Donor–Acceptor Cyclopropanes

      Lewis Acid Catalyzed Reactions of Donor–Acceptor Cyclopropanes with Anthracenes (pages 5329–5335)

      Olga A. Ivanova, Ekaterina M. Budynina, Yuri K. Grishin, Igor V. Trushkov and Pavel V. Verteletskii

      Article first published online: 30 SEP 2008 | DOI: 10.1002/ejoc.200800620

      Thumbnail image of graphical abstract

      Reactions of 2-aryl-1,1-cyclopropane diesters with anthracenes under Lewis acid catalysis afford three kinds of products depending on the substituents in anthracene and the nature of the aryl group in thecyclopropane. A formal [4+3] cycloaddition product, the product of cationic cyclization onto the aryl group of thestarting cyclopropane, and the common Friedel–Crafts products are obtained.

    14. Foiled Carbenes

      2-Methoxy-Δ3-1,3,4-oxadiazoline, a Multipurpose Precursor for the Generation of a Carbene, an Ylide, or a Diazo Compound (pages 5336–5345)

      Jean-Luc Mieusset, Peter Billing, Michael Abraham, Vladimir B. Arion, Lothar Brecker and Udo H. Brinker

      Article first published online: 22 SEP 2008 | DOI: 10.1002/ejoc.200800709

      Thumbnail image of graphical abstract

      Spirooxadiazoline 1 is shown to be a convenient precursor for the generation of foiled carbene 5. 5 can be trapped with alcohols with formation of the product with an anti-configuration. By photolysis carbene production is preceded by the formation of a diazo compound whereas thermally, an extremely unstable carbonyl ylide is generated first.

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