European Journal of Organic Chemistry

Cover image for Vol. 2013 Issue 1

January 2013

Volume 2013, Issue 1

Pages 4–196

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Microreview
    7. Short Communications
    8. Full Papers
    1. You have free access to this content
      Synthesis of a Spirocyclic Seco Structure of the Principal Vetiver Odorant Khusimone (Eur. J. Org. Chem. 1/2013)

      Philip Kraft and Natacha Denizot

      Article first published online: 14 DEC 2012 | DOI: 10.1002/ejoc.201290103

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      The cover picture illustrates, in a small comic strip, the difficulties of designing vetiver odorants from scratch. While vetiver oil is indispensible in perfumery, no synthetic vetiver odorant is yet available on the perfumer's palette. An empirical rule linked the olfactory properties of khusimone, the odorous principle of vetiver oil, to the distance between its α-branched carbonyl osmophore and the bulky gem-dimethyl moiety. Thus, 7,8-seco-khusimone was envisaged as a synthetic target, allegedly easier to synthesize than the natural lead. But life is not safe from frustration even if you reach your synthetic target, and the vetiver rule proved to be wrong as is further discussed in the article by P. Kraft and N. Denizot on p. 49 ff.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Microreview
    7. Short Communications
    8. Full Papers
    1. You have free access to this content
  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Microreview
    7. Short Communications
    8. Full Papers
    1. Graphical Abstract: Eur. J. Org. Chem. 1/2013 (pages 6–11)

      Article first published online: 14 DEC 2012 | DOI: 10.1002/ejoc.201290105

  4. News

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

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

      You have free access to this content
      Recent Progress in Nickel-Catalyzed Biaryl Coupling (pages 19–30)

      Junichiro Yamaguchi, Kei Muto and Kenichiro Itami

      Article first published online: 12 SEP 2012 | DOI: 10.1002/ejoc.201200914

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      Biaryl coupling through nickel catalysis has been known for a few decades. The topic has recently resurfaced in synthetic chemistry, however, thanks to its use of ideal coupling partners such as simple arenes (Ar–H) and phenol derivatives (Ar–OR). In this microreview, recent achievements in nickel-catalyzed biaryl coupling are summarized.

  6. Short Communications

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Microreview
    7. Short Communications
    8. Full Papers
    1. Gold-Catalyzed Mannich Reactions

      Gold-Catalyzed Mannich Addition Reactions of 1,3-Dicarbonyl Compounds with N-Protected Imines (pages 31–34)

      Manuela Delgado-Rebollo, Rocio Moreno, Manuel R. Fructos and Auxiliadora Prieto

      Article first published online: 26 NOV 2012 | DOI: 10.1002/ejoc.201201252

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      The Mannich addition reaction of different N-protected imines with β-keto esters and 1,3-diketones is efficiently performed by using the gold IPrAuNTf2 complex under mild conditions.

    2. Intramolecular Hydroamination

      Silver-Catalyzed Cyclization of N-(Prop-2-yn-1-yl)pyridin-2-amines (pages 35–39)

      Mourad Chioua, Elena Soriano, Lourdes Infantes, M. Luisa Jimeno, José Marco-Contelles and Abdelouahid Samadi

      Article first published online: 19 NOV 2012 | DOI: 10.1002/ejoc.201201258

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      The silver-catalyzed cycloisomerization of readily available N-(prop-2-yn-1-ylamino)pyridines is a new and practical method for the synthesis of differently substituted 3-methylimidazo[1,2-a]pyridines, suitable intermediates for further synthetic transformations and modulation, that proceeds under mild reaction conditions to give good-to-high yields and excellent regioselectivity.

    3. Cycloaddition

      Cycloaddition of 2-Methyleneaziridines with Isocyanates Catalyzed by Tin Iodide (pages 40–43)

      Hiroki Takahashi, Seiji Yasui, Shinji Tsunoi and Ikuya Shibata

      Article first published online: 13 NOV 2012 | DOI: 10.1002/ejoc.201201305

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      2-Methyleneaziridines proved to be good substrates for the cycloaddition with isocyanates, for which a tin iodide system, Bu2SnI2–LiI, was employed as an effective catalyst. Products were derived from N-attack of the ring-opened metalloenamine intermediate.

    4. Dewar Benzene

      Synthesis of 1,2,3,4-Tetramethyl- and 1,2,3,4-Tetraethylfluorene through a Dewar Benzene Pathway (pages 44–47)

      Štěpánka Janková, Jiří Schulz, Simona Hybelbauerová, Ivana Císařová, Petr Štěpnička and Martin Kotora

      Article first published online: 21 NOV 2012 | DOI: 10.1002/ejoc.201201343

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      Diels–Alder reactions of substituted cyclobutadiene–AlCl3 complexes with methyl phenylpropynoate provide Dewar benzenes, which undergo further transformations, including hydrolysis, photochemical rearrangement, intramolecular Friedel–Crafts reaction, and reduction, to provide 1,2,3,4-alkylfluorenones and -fluorenes. A Ru complex with 1,2,3,4-tetraethylfluorenone is prepared.

  7. Full Papers

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

      Synthesis of a Spirocyclic Seco Structure of the Principal Vetiver Odorant Khusimone (pages 49–58)

      Philip Kraft and Natacha Denizot

      Article first published online: 26 NOV 2012 | DOI: 10.1002/ejoc.201201318

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      Dissecting the bond between the methylene and the gem-dimethyl unit of khusimone leads to a spirocycle of almost identical shape, which was synthesized by 1,4-conjugate addition of a vinyl Gilman reagent, Mukaiyama aldol condensation of a bromo aldehyde prepared by Ireland–Claisen rearrangement of allyl isovalerate, and subsequent cyclization.

    2. Natural Products

      Iron-Mediated Total Synthesis of 2,7-Dioxygenated Carbazole Alkaloids (pages 59–64)

      Micha P. Krahl, Olga Kataeva, Arndt W. Schmidt and Hans-Joachim Knölker

      Article first published online: 21 NOV 2012 | DOI: 10.1002/ejoc.201201251

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      Four 2,7-dioxygenated carbazole alkaloids, clausine O, clausine H (clauszoline-C), and the anti-HIV active 7-methoxy-O-methylmukonal and clausine K (clauszoline-J), have been synthesized by using an iron-mediated approach for the construction of the carbazole framework.

    3. Carbohydrate Recognition

      Differential Recognition of Mannose-Based Polysaccharides by Tripodal Receptors Based on a Triethylbenzene Scaffold Substituted with Trihydroxybenzoyl Moieties (pages 65–76)

      Paula Carrero, Ana Ardá, Mónica Alvarez, Elisa G. Doyagüez, Eva Rivero-Buceta, Ernesto Quesada, Alicia Prieto, Dolores Solís, María José Camarasa, María Jesús Peréz-Pérez, Jesús Jiménez-Barbero and Ana San-Félix

      Article first published online: 9 NOV 2012 | DOI: 10.1002/ejoc.201201239

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      Two tripodal receptors based on a triethylbenzene scaffold substituted with trihydroxybenzoyl groups have been synthesised, and their conformational preferences and carbohydrate-binding ability have been evaluated. One of them has a pre-organisation that allows the recognition, in DMSO, of mannose-containing polysaccharides that mimic the envelope or cell-wall polysaccharides of certain pathogens. These results open attractive perspectives for the development and potential application of 2 or compounds derived thereof in future antiinfective strategies.

    4. Total Synthesis

      Total Syntheses and Biological Evaluation of 3-O-Methylfunicone and Its Derivatives Prepared by TMPZnCl·LiCl-Mediated Halogenation and Carbonylative Stille Cross-Coupling (pages 77–83)

      Michael Ehrlich and Thomas Carell

      Article first published online: 19 NOV 2012 | DOI: 10.1002/ejoc.201201256

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      The total syntheses of the natural product 3-O-methylfunicone and its derivatives has been accomplished. The key reactions are TMPZnCl·LiCl-mediated iodination and a carbonylative Stille cross-coupling reaction. In addition, the inhibitory effect of the synthesized compounds have been evaluated against Y-family DNA polymerases κ and η by primer extension experiments.

    5. Donor-Acceptor Systems

      Metal-Free Benzodithiophene-Containing Organic Dyes for Dye-Sensitized Solar Cells (pages 84–94)

      Elena Longhi, Alberto Bossi, Gabriele Di Carlo, Stefano Maiorana, Filippo De Angelis, Paolo Salvatori, Annamaria Petrozza, Maddalena Binda, Vittoria Roiati, Patrizia Romana Mussini, Clara Baldoli and Emanuela Licandro

      Article first published online: 22 NOV 2012 | DOI: 10.1002/ejoc.201200958

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      Two donor–acceptor metal-free organic dyes, CR29 and CR52, featuring two isomeric benzodithiophene (BDT1 or BDT) π-spacers have been synthesized. The dyes display good extinction coefficients in the visible spectral region 400–650 nm and promising performance in DSSC. Theoretical and experimental investigations established that in such architectures, the BDT1-based dye outperformed the BDT-based dye.

    6. Selective Imide Reduction

      The High Selectivity of the Cp2ZrHCl Reducing Agent for Imides: A Combined Experimental and Theoretical Study on γ-Lactam and Isoxazolidinone Derivatives (pages 95–104)

      Giuseppe Lanza, Maria A. Chiacchio, Salvatore V. Giofrè, Roberto Romeo and Pedro Merino

      Article first published online: 21 NOV 2012 | DOI: 10.1002/ejoc.201201186

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      Semicyclic imides such as γ-lactam and isoxazolidinone derivatives are efficiently and selectivity reduced by the Cp2ZrHCl agent. The energetic reaction pathways for endo and exo attack, computed at the DFT level including thermal effects, allow an exhaustive interpretation of current and previously reported experimental data.

    7. Furan Synthesis

      Direct Access to Fully Substituted 3-Formyl-4-iodofurans through Iodocyclization of α-Alkynyl β-Alkoxy Enones (pages 105–110)

      Guillaume Raffa, Geneviève Balme and Nuno Monteiro

      Article first published online: 12 NOV 2012 | DOI: 10.1002/ejoc.201201203

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      Fully substituted 3-formyl-4-iodofurans are easily accessible under mild reaction conditions from readily available α-iodo β-alkoxy enones and terminal alkynes. The proposed two-step protocol combines a Sonogashira cross-coupling reaction and subsequent iodocyclization without the need to isolate the intermediate α-alkynyl β-alkoxy enone.

    8. Diastereoselective Lithiation

      Explanation of Different Regioselectivities in the ortho-Lithiation of Ferrocenyl(phenyl)methanamines (pages 111–116)

      Ambroz Almássy, Andrea Škvorcová, Branislav Horváth, Filip Bilčík, Vladimír Bariak, Erik Rakovský and Radovan Šebesta

      Article first published online: 20 NOV 2012 | DOI: 10.1002/ejoc.201201325

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      Diastereoselective ortho-lithiation of ferrocenyl(phenyl)methanamines was studied by 7Li NMR spectroscopy and DFT calculations. The configurations of the phosphane products were confirmed by X-ray crystallography. The different facial selectivities of the lithiation can be explained by the multicenter arrangement of the dilithium transition state, which features also Fe–Li interactions.

    9. Cross-Coupling

      Pd-Catalyzed Chemoselective Cross-Coupling Reaction of Triaryl- or Triheteroarylbismuth Compounds with 3,6-Dihalopyridazines (pages 117–124)

      Karène Urgin, Christophe Aubé, Muriel Pipelier, Virginie Blot, Christine Thobie-Gautier, Stéphane Sengmany, Jacques Lebreton, Eric Léonel, Didier Dubreuil and Sylvie Condon

      Article first published online: 9 NOV 2012 | DOI: 10.1002/ejoc.201200977

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      The cross-coupling reactions of 3,6-dihalopyridazines with triaryl- or triheteroarylbismuth compounds were performed under palladium catalysis. The reaction was highly chemoselective, affording functionalized aryl- or heteroarylpyridazinyl chlorides in moderate to good yields.

    10. Glycosyl Iodides

      Polymethylhydrosiloxane (PMHS): A Convenient Option for Synthetic Applications of the Iodine/Silane Combined Reagent – Straightforward Entries to 2-Hydroxyglycals and Useful Building-Blocks of Glucuronic Acid and Glucosamine (pages 125–131)

      Maddalena Giordano and Alfonso Iadonisi

      Article first published online: 9 NOV 2012 | DOI: 10.1002/ejoc.201201084

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      Polymethylhydrosiloxane (PMHS) is a practically convenient alternative to triethylsilane in a large set of synthetic elaborations entailing the quick generation of glycosyl iodides with a iodine/silane combined reagent.

    11. Nitrogen Heterocycles

      An Efficient Catalytic Method for Regioselective Sulfenylation of Electron-Rich Aza-Aromatics at Room Temperature (pages 132–140)

      Enrico Marcantoni, Roberto Cipolletti, Laura Marsili, Stefano Menichetti, Roberta Properzi and Caterina Viglianisi

      Article first published online: 19 NOV 2012 | DOI: 10.1002/ejoc.201201100

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      A useful method for the regioselective introduction of the sulfenyl group into electron-rich aza-aromatics using S-alkyl- and S-arylthiophthalimides as sulfenylating agents is described. Catalytic amounts of CeCl3·7H2O/NaI are crucial to the promotion of this regioselective carbon–sulfur-bond-forming electrophilic aromatic substitution reaction.

    12. Organocatalysis

      The Stability of Imidazolidinones is the Primary Influence on the Catalytic Activity of Proline Amides and Proline Sulfonamides in Enamine Catalysis Using Alkyl Aldehyde Substrates (pages 141–147)

      Sergey Tin, José A. Fuentes, Tomas Lebl and Matthew L. Clarke

      Article first published online: 9 NOV 2012 | DOI: 10.1002/ejoc.201201174

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      Some proline amides are poor catalysts when aldehydes are used as substrates since the catalysts irreversibly form imidazolidinones. Proline amides with more basic amide groups form long-lived enamines, which allows catalysis to proceed. Proline sulfonamides only form imidazolidones, but these are unstable.

    13. Iron Catalysis

      Iron-Catalyzed Diastereoselective Synthesis of α-(Methoxycarbonyl)allylsilanes (pages 148–154)

      Guobi Chai, Rong Zeng, Chunling Fu and Shengming Ma

      Article first published online: 15 NOV 2012 | DOI: 10.1002/ejoc.201201209

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      Treatment of 1-(trimethylsilyl)allene-1-carboxylates with Grignard reagents under iron catalysis conditions afforded stereodefined polysubstituted α-(methoxycarbonyl)allylsilanes in good to excellent yields. In addition, the products could be further applied to the stereocontrolled synthesis α,β-alkenoates, a β,γ-alkenoate, and an allylic fluoride.

    14. Molecular Diversity

      Synthesis and Regioselective Functionalization of Piperazin-2-ones Based on Phe-Gly Pseudodipeptides (pages 155–161)

      Angel M. Valdivielso, Pilar Ventosa-Andrés, M. Teresa García-López, Rosario Herranz and Marta Gutiérrez-Rodríguez

      Article first published online: 21 NOV 2012 | DOI: 10.1002/ejoc.201201221

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      An easy methodology for the synthesis of the piperazin-2-ones by one-pot reductive cyclization of PheΨ[CH(CN)NH]Gly pseudodipeptides is described. Study of the reactivity of the piperazin-2-one ring has shown that regioselective functionalization at the N1 and N4 positions is possible, and hence great potential for molecular diversity generation

    15. Natural Products

      Evolution of Concise and Flexible Synthetic Strategies for Trichostatic Acid and the Potent Histone Deacetylase Inhibitor Trichostatin A (pages 162–172)

      Casey C. Cosner, Vijaya Bhaskara Reddy Iska, Anamitra Chatterjee, John T. Markiewicz, Steven J. Corden, Joakim Löfstedt, Tobias Ankner, Joshua Richer, Tyler Hulett, Douglas J. Schauer, Olaf Wiest and Paul Helquist

      Article first published online: 20 NOV 2012 | DOI: 10.1002/ejoc.201201233

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      Three synthetic strategies have been developed for trichostatic acid and trichostatin A. Each strategy has a different key bond-forming step; a vinylogous Horner–Wadsworth–Emmons condensation, a Marshall propargylation, and coupling of a ketone enolate with various alkenyl halides. Two of the syntheses were efficient and able to produce analogues. Two of the syntheses were enantioselective.

    16. Natural Product Synthesis

      Chemoenzymatic Total Synthesis of a Naturally Occurring (5-5′)/(8′-O-4″) Dehydrotrimer of Ferulic Acid (pages 173–179)

      Louis M. M. Mouterde, Amandine L. Flourat, Molly M. M. Cannet, Paul-Henri Ducrot and Florent Allais

      Article first published online: 26 NOV 2012 | DOI: 10.1002/ejoc.201201290

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      The first total convergent synthesis of the naturally occurring (5-5′)/(8′-O-4″) dehydrotrimer of ferulic acid (A) has been achieved in 10 steps and in 18 % yield starting from commercially available vanillin using horseradish peroxidase mediated enzymatic aryl–aryl coupling, aldolization/crotonization, and Wittig olefination reactions as the key steps.

    17. Synthesis of the AB-Ring Pyranolactone Substructure of Granaticin A (pages 180–190)

      Ruben Bartholomäus, Janina Bachmann, Christian Mang, Lars Ole Haustedt, Klaus Harms and Ulrich Koert

      Article first published online: 30 OCT 2012 | DOI: 10.1002/ejoc.201201279

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      Synthesis of the AB-ring substructure of granaticin A was accomplished. The pyranolactone moiety was stereoselectively accessed by Sharpless asymmetric dihydroxylation and oxa-Pictet–Spengler cyclization. Ozonolysis of a hydroquinone led to pyranolactone anhydrides. Regioselective addition of a Grignard reagent to an unsymmetrical anhydride was observed. An alternative strategy was also investigated.

    18. Alkaloid Synthesis

      Total Synthesis of Taspine and a Symmetrical Analogue: Study of Binding to G-Quadruplex DNA by ESI-MS (pages 191–196)

      Alessandro Altieri, Marco Franceschin, Daniele Nocioni, Antonello Alvino, Valentina Casagrande, Maria Luisa Scarpati and Armandodoriano Bianco

      Article first published online: 21 NOV 2012 | DOI: 10.1002/ejoc.201201034

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      We report the total synthesis of taspine and its symmetrical analogue TAS2C. Both the synthesised compounds were tested by ESI-MS for their ability to bind different quadruplex and duplex DNA structures.

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