European Journal of Organic Chemistry

Cover image for Vol. 2012 Issue 36

December 2012

Volume 2012, Issue 36

Pages 7003–7153

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correction
    1. You have free access to this content
      How are Biogenic Amines Metabolized by Monoamine Oxidases? (Eur. J. Org. Chem. 36/2012)

      Robert Vianello, Matej Repič and Janez Mavri

      Version of Record online: 4 DEC 2012 | DOI: 10.1002/ejoc.201290099

      Thumbnail image of graphical abstract

      The cover picture shows a scheme of the rate-limiting first step of dopamine metabolism catalyzed by the flavoenzyme monoamine oxidase. The enzyme uses the flavin adenine dinucleotide (FAD) cofactor to perform its catalytic activity through the process initiated by an α-CH abstraction from the substrate. Over the years, there has been a heated debate whether the hydrogen is transferred as a proton, a radical or a hydride. Our work presents substantial evidence in favour of the hydride transfer mechanism. This reaction produces a covalent adduct between the hydrided anionic FADH and the cationic substrate, to be followed by the deprotonation of the free amino group in the second step, releasing final products, fully reduced flavin, FADH2 and the neutral trans-imine. Details of the most feasible hydride mechanism are discussed in the article by R. Vianello et al. on p. 7057 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. Correction
  3. News

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

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    1. Tröger's Base at 125

      The 125th Anniversary of the Tröger's Base Molecule: Synthesis and Applications of Tröger's Base Analogues (pages 7015–7041)

      Ögmundur Vidar Rúnarsson, Josep Artacho and Kenneth Wärnmark

      Version of Record online: 20 NOV 2012 | DOI: 10.1002/ejoc.201201249

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      Tröger's base [TB, (±)-1] has a unique position in the history of stereochemistry. Since the first use of TB analogues as synthetic receptors less than 30 years ago, interest in the system has exploded thanks to the development of new methods for TB functionalization (virtually all position in the skeleton are now accessible). We focus on synthetic advances and recent applications of TB chemistry.

  5. Short Communications

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    1. Trifluoromethylindium Reagents

      Direct Preparation of Trifluoromethylindium Reagents from Trifluoromethyl Iodide: Effective Trifluoromethylation and Perfluoroalkylation Reagents (pages 7043–7047)

      Motohiro Fujiu, Yuzo Nakamura, Hiroki Serizawa, Kohsuke Aikawa, Shigekazu Ito and Koichi Mikami

      Version of Record online: 9 NOV 2012 | DOI: 10.1002/ejoc.201201116

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      The direct synthesis of trifluoromethylindium reagents prepared from trifluoromethyl iodide by using just one equivalent each of indium, lithium chloride or sodium iodide, and ferrocene is reported. The carbonyl addition reactions of these trifluoromethylindium reagents were studied.

    2. Nucleophilic Aromatic Substitution

      Regioselective Preparation of 3-Alkoxy-4,5-difluoroanilines by SNAr (pages 7048–7052)

      Sven Van Brandt, Frederik J. R. Rombouts, Carolina Martínez-Lamenca, Jos Leenaerts, Tom R. M. Rauws and Andrés A. Trabanco

      Version of Record online: 15 NOV 2012 | DOI: 10.1002/ejoc.201201228

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      Nucleophilic aromatic meta-substitution of 3,4,5-trifluoroaniline was optimized and exemplified with a diverse set of alcohols. The conditions are cheap, simple, and highly scalable. Variation of both the nucleophile and the electrophile was explored.

    3. Reductive Elimination

      Demethylenation of Tröger's Bases with Concomitant Hydrazine Formation (pages 7053–7056)

      Xuefeng Gao, Carissa S. Hampton and Michael Harmata

      Version of Record online: 6 NOV 2012 | DOI: 10.1002/ejoc.201201341

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      Reductive elimination of methylene carbene is formally achieved when Tröger's bases are treated with dimethyldioxirane to produce the corresponding N-oxides and then reacted with acetic anhydride. The resulting products are a unique class of hydrazines.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
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    8. Correction
    1. Enzymatic Amine Oxidation

      How are Biogenic Amines Metabolized by Monoamine Oxidases? (pages 7057–7065)

      Robert Vianello, Matej Repič and Janez Mavri

      Version of Record online: 25 OCT 2012 | DOI: 10.1002/ejoc.201201122

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      Computations have revealed that the monoamine oxidase catalysed transformation of amine neurotransmitters to neutral imines is a two-step process, which, in the rate-limiting first step, involves a direct α-CH hydride abstraction by the flavin N5 atom. This is followed by flavin N1 deprotonation of the substrate free amino group, facilitated with two water molecules.

    2. Tröger's Base Analogues

      Synthesis of Symmetrical Dinitro- and Diamino-Substituted Tröger's Base Analogues (pages 7066–7074)

      Jiří Šturala and Radek Cibulka

      Version of Record online: 15 NOV 2012 | DOI: 10.1002/ejoc.201201188

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      Nitration of halogenated Tröger's bases with potassium nitrate in sulfuric acid leads regioselectively to halogenated dinitro derivatives. These can be chemoselectively reduced in high yields either to diamino-substituted Tröger's bases or to halogenated diamino-substituted Tröger's bases.

    3. Arylation of Heterocycles

      Direct C-3-Arylations of 1H-Indazoles (pages 7075–7081)

      Ali Ben-Yahia, Mohammed Naas, Saïd El Kazzouli, El Mokhtar Essassi and Gérald Guillaumet

      Version of Record online: 7 NOV 2012 | DOI: 10.1002/ejoc.201200860

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      A new C-3 arylation method for 1H-indazoles was developed. Various C-3-arylated products were prepared using Pd(OAc)2, 1,10-phenanthroline, and K2CO3 in refluxing DMA.

    4. Alkaloid Synthesis

      Synthesis and Biological Activities of the 3,5-Disubstituted Indolizidine Poison Frog Alkaloid 239Q and Its Congeners (pages 7082–7092)

      Xu Wang, Hiroshi Tsuneki, Noriko Urata, Yasuhiro Tezuka, Tsutomu Wada, Toshiyasu Sasaoka, Hideki Sakai, Ralph A. Saporito and Naoki Toyooka

      Version of Record online: 7 NOV 2012 | DOI: 10.1002/ejoc.201200974

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      The first total synthesis of the 3,5-disubstituted indolizidine toad alkaloid 239Q has been achieved. The relative stereochemistry of natural 239Q was determined unambiguously by comparison of GC-FTIR spectra of synthetic material with skin extracts of Melanophryniscus cupreuscapularis. The C7 congeners at the 5-position showed strong antagonist activities on α4β2 nicotinic acetylcholine receptors.

    5. Selective Epoxidation

      Epoxidation of 4-Alkylidenecyclopentenones: A Route to the 1-Oxaspiro[2.4]hept-6-en-5-one Framework (pages 7093–7105)

      Mohammed Ahmar, Stéphane Thomé and Bernard Cazes

      Version of Record online: 30 OCT 2012 | DOI: 10.1002/ejoc.201201030

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      4-Alkylidenecyclopentenones are regioselectively epoxidized on their exocyclic double bonds by meta-chloroperbenzoic acid to give spiroepoxycyclopentenones. Under acidic conditions these undergo ring-opening to afford 4-hydroxy-4-(1-hydroxyalkyl)cyclopentenones.

    6. N-Methylated Peptides

      Microwave Heating in the Solid-Phase Synthesis of N-Methylated Peptides: When Is Room Temperature Better? (pages 7106–7111)

      Renée Roodbeen, Søren L. Pedersen, Masood Hosseini and Knud J. Jensen

      Version of Record online: 7 NOV 2012 | DOI: 10.1002/ejoc.201201050

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      A robust, rapid, easy and high-yielding microwave-assisted method for the solid-phase synthesis of N-methylated peptides using COMU has been developed. Fmoc-Arg(Pbf)-OH was incorporated in higher yields at room temperature than at elevated temperature as a result of intramolecular Arg lactam formation, which competes with intermolecular amide bond formation.

    7. Nitrogen Heterocycles

      Comparative Study of the Regioselectivity and Reaction Media for the Synthesis of 1-tert-Butyl-3(5)-trifluoromethyl-1H-pyrazoles (pages 7112–7119)

      Marcos A. P. Martins, Mara R. B. Marzari, Clarissa P. Frizzo, Marcileia Zanatta, Lilian Buriol, Valquiria P. Andrade, Nilo Zanatta and Helio G. Bonacorso

      Version of Record online: 6 NOV 2012 | DOI: 10.1002/ejoc.201201111

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      A series of new 1-tert-butyl-3(5)-trifluoromethyl-1H-pyrazoles were synthesized with high regioselectivity. Addition of 1-butyl-3-methylimidazolium tetrafluoroborate and pyridine led to a mixture of regioisomers. Adding a weak acid resulted in the loss of the tert-butyl group. The addition of a strong acid led to the 1,3 isomer, whereas addition of base led to the 1,5 isomer.

    8. Amino Acid Synthesis

      Synthesis of γ-Oxo γ-Aryl and γ-Aryl α-Amino Acids from Aromatic Aldehydes and Serine (pages 7120–7128)

      Shibin Chacko and Ramesh Ramapanicker

      Version of Record online: 2 NOV 2012 | DOI: 10.1002/ejoc.201201128

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      An efficient synthesis of γ-oxo α-amino acids and γ-aryl α-amino acids with very high enantiopurity, starting from serine and aromatic aldehydes, is reported.

    9. Organocatalysis

      Simple Ionic Liquid Supported C2-Symmetric Bisprolinamides as Recoverable Organocatalysts for the Asymmetric Aldol Reaction in the Presence of Water (pages 7129–7134)

      Sergei V. Kochetkov, Alexandr S. Kucherenko, Galina V. Kryshtal, Galina M. Zhdankina and Sergei G. Zlotin

      Version of Record online: 6 NOV 2012 | DOI: 10.1002/ejoc.201201144

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      Ionic liquid supported C2-symmetric (S)-prolinamides bearing achiral diamine units were synthesized. The potency of these prolinamides as efficient and reusable (over 15 cycles) organocatalysts for asymmetric aldol reactions of cyclic or linear ketones with aromatic (heteroaromatic) aldehydes in the presence of water was demonstrated.

    10. Heterasumanenes

      Synthesis, Structures, and Optical Properties of Heterasumanenes Containing Group 14 Elements and Their Related Compounds (pages 7135–7142)

      Tomoharu Tanikawa, Masaichi Saito, Jing Dong Guo, Shigeru Nagase and Mao Minoura

      Version of Record online: 30 OCT 2012 | DOI: 10.1002/ejoc.201201223

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      Repetitive lithiation of triphenylene followed by introduction of germanium functionalities resulted in the formation of new compounds. Tin congeners were also synthesized and investigated. The optical properties of trigermasumanene and its derivatives were investigated, and theoretical calculations were carried out to understand the properties of the triphenylenometallole derivatives.

    11. Dual Enantioselective Control

      Functionalized N-Heterocyclic Carbene Ligands for Dual Enantioselective Control in the Cu-Catalyzed Conjugate Addition of Dialkylzinc Compounds to Acyclic Enones (pages 7143–7152)

      Kenta Dohi, Junko Kondo, Haruka Yamada, Ryuichi Arakawa and Satoshi Sakaguchi

      Version of Record online: 7 NOV 2012 | DOI: 10.1002/ejoc.201201082

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      Functionalized azolium salts have been synthesized from chiral α-amino acid derivatives. The asymmetric conjugate addition (ACA) of R2Zn to acyclic enones in the presence of a Cu salt and (hydroxy amide)-functionalized azoliums at room temperature gave the 1,4-adducts with good enantioselectivity. The stereoselectivity was reversed in ACA reactions with (ester amide)-functionalized azolium salts.

  7. Correction

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correction
    1. You have free access to this content
      Synthesis of Precursors for Large-Diameter Hemispherical Buckybowls and Precursors for Short Carbon Nanotubes (page 7153)

      Andreas Mueller and Konstantin Yu. Amsharov

      Version of Record online: 21 NOV 2012 | DOI: 10.1002/ejoc.201201448

      This article corrects:

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