European Journal of Organic Chemistry

Cover image for Vol. 2014 Issue 12

April 2014

Volume 2014, Issue 12

Pages 2403–2611

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communication
    7. Full Papers
    1. You have free access to this content
      Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept (Eur. J. Org. Chem. 12/2014)

      Fabien Toulgoat, Sébastien Alazet and Thierry Billard

      Article first published online: 11 APR 2014 | DOI: 10.1002/ejoc.201490030

      Thumbnail image of graphical abstract

      The cover picture shows the “hot topics” of fluorine chemistry. In particular, the emergence of new fluorinated moieties which, in recent years, have found more and more applications in various fields, from materials to life sciences and medical imaging. Among these emergent groups, CF3S recently experienced a “Renaissance” period with the development of new reagents to enable its introduction into molecules. Details are presented in the Microreview by T. Billard et al. on p. 2415 ff..

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communication
    7. Full Papers
    1. Graphical Abstract: Eur. J. Org. Chem. 12/2014 (pages 2403–2409)

      Article first published online: 11 APR 2014 | DOI: 10.1002/ejoc.201490032

  3. News

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

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

      Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept (pages 2415–2428)

      Fabien Toulgoat, Sébastien Alazet and Thierry Billard

      Article first published online: 12 FEB 2014 | DOI: 10.1002/ejoc.201301857

      Thumbnail image of graphical abstract

      The CF3S group, owing to its high lipophilicity, has continuously received attention. In the past, trifluoromethylthiolation reactions were performed by using mainly two complementary reagents, that is, CF3SCl and CF3SM+. Recently, the organic chemist's toolbox has gained new efficient methods based on transition-metal catalysis and new easy-to-handle reagents.

  5. Short Communication

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

      Mannich-Type Addition Reactions between Lithium Derivatives of Benzo[d]thiazoles and N-tert-Butylsulfinyl-3,3,3-trifluoroacetaldimine: Convenient Generalized Synthesis of Bis(benzothiazole)s (pages 2429–2433)

      Haibo Mei, Yanling Dai, Lingmin Wu, Vadim A. Soloshonok, Jianlin Han and Yi Pan

      Article first published online: 17 MAR 2014 | DOI: 10.1002/ejoc.201400118

      Thumbnail image of graphical abstract

      This study describes the anomalous outcome of the Mannich-type reaction of N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimine and Li derivatives of benzo[d]thiazoles, which provides a convenient and generalized synthetic method for the preparation of biologically relevant (E)-1,2-bis(2-benzothiazolyl)ethanes.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communication
    7. Full Papers
    1. Anion–π Interactions

      Single-Crystal X-ray Diffraction and Solution Studies of Anion–π Interactions in N-(Pentafluorobenzyl)pyridinium Salts (pages 2435–2442)

      Michael Giese, Markus Albrecht, Tatjana Repenko, Johannes Sackmann, Arto Valkonen and Kari Rissanen

      Article first published online: 17 JAN 2014 | DOI: 10.1002/ejoc.201301336

      Thumbnail image of graphical abstract

      The interactions of N-(pentafluorobenzyl)pyridinium salts are investigated in the solid state as well as in solution. The triiodide salt shows distinct evidence of anion–π interactions with both the pyridinium and the pentafluorophenyl unit. Solution investigations to prove the attractive nature of the noncovalent force failed, but they did not rule out the presence of the interaction.

    2. Diels–Alder Reaction

      Diels–Alder Reaction of Ethyl 3-Benzamido-2-oxo-6-(trifluoromethyl)-2H-pyran-5-carboxylate with Alkoxyalkenes as an Effective Approach to Trifluoromethyl-Containing 3-Aminobenzoic Acid Derivatives (pages 2443–2450)

      Ivan S. Kondratov, Nataliya A. Tolmachova, Violetta G. Dolovanyuk, Igor I. Gerus, Klaus Bergander, Constantin-Gabriel Daniliuc and Günter Haufe

      Article first published online: 23 JAN 2014 | DOI: 10.1002/ejoc.201301485

      Thumbnail image of graphical abstract

      The Diels–Alder reactions of ethyl 3-benzamido-2-oxo-6-(trifluoromethyl)-2H-pyran-5-carboxylate with ethyl vinyl ether, 2-methoxypropene, and 1-ethoxypropene were investigated under different reaction conditions.

    3. Ti-Mediated Aldol Addition

      Synthetic Routes towards Fluorine-Containing Amino Sugars: Synthesis of Fluorinated Analogues of Tomosamine and 4-Amino-4-deoxyarabinose (pages 2451–2459)

      Christopher Albler and Walther Schmid

      Article first published online: 23 JAN 2014 | DOI: 10.1002/ejoc.201301614

      Thumbnail image of graphical abstract

      4-Amino-2-fluoropentoses and -hexoses were prepared through two-carbon chain elongations by Ti-mediated aldol additions of serine- and threonine-derived amino aldehydes to fluoroacetyl-ephedrine-oxazolidinone. Excellent stereoselectivities were attained for matched-case fluorohydrins, which were deprotected in a short sequence.

    4. Indole Derivatives

      Facile Synthesis of 2-(Perfluoroalkyl)indoles through a Michael Addition/CuI-Catalyzed Annulation Process (pages 2460–2467)

      Long Cao, Dandane Shen, Jiamei Wei, Jie Chen, Hongmei Deng, Min Shao, Jumei Shi, Hui Zhang and Weiguo Cao

      Article first published online: 13 MAR 2014 | DOI: 10.1002/ejoc.201400056

      Thumbnail image of graphical abstract

      A facile synthesis of 2-perfluoroalkylated indole derivatives was developed that proceeds through an intermolecular Michael addition and subsequent copper-catalyzed intramolecular C–C coupling process. This one-pot method provided a wide variety of functionalized methyl 2-(perfluoroalkyl)-1H-indole-3-carboxylates in good to excellent yields.

    5. Heterocyclic Chemistry

      One-Pot Synthesis of 2-Imino-4-(trifluoromethyl)thiazolidin-4-ol Derivatives in a Three-Component Reaction: Application to Structurally Diverse Scaffolds of Biological Interest Through Subsequent Reactions (pages 2468–2479)

      Tulshiram Dalmal, K. Appalanaidu, Umesh B. Kosurkar, N. Jagadeesh Babu and Ravindra M. Kumbhare

      Article first published online: 26 FEB 2014 | DOI: 10.1002/ejoc.201301710

      Thumbnail image of graphical abstract

      A one-pot, three-component reaction for the synthesis of 2-imino-4-(trifluoromethyl)thiazolidin-4-ol derivatives is described. Subsequent reactions of the products allow the synthesis of various scaffolds, including isoxazoles, triazoles, and propargylamine derivatives.

    6. Carbenoid Functionalization

      Cu-Catalyzed Carbenoid Functionalization of Indoles by Methyl 3,3,3-Trifluoro-2-diazopropionate (pages 2480–2486)

      Irina E. Tsyshchuk, Daria V. Vorobyeva, Alexander S. Peregudov and Sergey N. Osipov

      Article first published online: 3 FEB 2014 | DOI: 10.1002/ejoc.201301734

      Thumbnail image of graphical abstract

      An efficient Cu-catalyzed direct CH-functionalization of indoles with methyl 3,3,3-trifluoro-2-diazopropionate has been developed. The reactions proceed within a few minutes under low catalyst loading to give the corresponding C3 or C2 substitution products with high regioselectivity. This method has been successfully applied for the synthesis of trifluoromethyl-containing paullone.

    7. Fluorinated Heterocycles

      One-Pot Synthesis of CF3-Substituted Pyrazolines/Pyrazoles from Electron-Deficient Alkenes/Alkynes and CF3CHN2 Generated in situ: Optimized Synthesis of Tris(trifluoromethyl)pyrazole (pages 2487–2495)

      Evgeniy Y. Slobodyanyuk, Olexiy S. Artamonov, Oleg V. Shishkin and Pavel K. Mykhailiuk

      Article first published online: 5 MAR 2014 | DOI: 10.1002/ejoc.201301852

      Thumbnail image of graphical abstract

      Three-component reaction between CF3CH2NH2·HCl, NaNO2 and electron-deficient alkenes/alkynes gives CF3-substituted pyrazolines/pyrazoles at room temperature in excellent yields.

    8. Total Synthesis

      Total Synthesis of Unsymmetrical Benzils, Scandione and Calophione A (pages 2496–2507)

      Rattana Worayuthakarn, Sasiwadee Boonya-udtayan, Somsak Ruchirawat and Nopporn Thasana

      Article first published online: 20 FEB 2014 | DOI: 10.1002/ejoc.201301722

      Thumbnail image of graphical abstract

      A convergent synthesis of the title benzils, which embody the 1,2-diarylethane-1,2-dione system, is reported. Key steps involve intramolecular cyclization of the carbanion at the benzylic position of the arylbenzyl ether to the adjacent ester group followed by oxidation. The palladium(II)-catalyzed oxidative cyclization was also studied to establish the benzofuran unit of calophione A.

    9. Domino Reactions

      Synthesis of Indoles by Domino Reaction of 2-(Tosylamino)benzyl Alcohols with Furfurylamines: Two Opposite Reactivity Modes of the α-Carbon of the Furan Ring in One Process (pages 2508–2515)

      Maxim G. Uchuskin, Natalia V. Molodtsova, Sergey A. Lysenko, Vladimir N. Strel'nikov, Igor V. Trushkov and Alexander V. Butin

      Article first published online: 20 FEB 2014 | DOI: 10.1002/ejoc.201301762

      Thumbnail image of graphical abstract

      Furfurylamines react with 2-(tosylamino)benzyl alcohols affording 2-(2-acylvinyl)indoles by a domino reaction sequence in which the same furan α-carbon atom behaves initially as an electron-rich center and then as an electron deficient one. In addition, substitution of the tosylamino leaving group with a phthalimido group furnishes a change in chemoselectivity.

    10. Green Synthesis

      Facile Non-Catalyzed Synthesis of Tertiary Phosphine Sulfides by Regioselective Addition of Secondary Phosphine Sulfides to Alkenes (pages 2516–2521)

      Svetlana F. Malysheva, Nina K. Gusarova, Alexander V. Artem'ev, Nataliya A. Belogorlova, Alexander I. Albanov, Tatyana N. Borodina, Vladimir I. Smirnov and Boris A. Trofimov

      Article first published online: 14 FEB 2014 | DOI: 10.1002/ejoc.201301786

      Thumbnail image of graphical abstract

      Secondary phosphine sulfides easily add to diverse terminal and internal alkenes (hept-1-ene, cyclohexene, styrenes, allyl alcohol, vinyl ethers, vinyl sulfides, vinyltrimethylsilane, 1-vinylimidazoles, vinyl acetate) under catalyst- and solvent-free conditions at 80 °C (4–44 h) to afford the corresponding anti-Markovnikov adducts in good to excellent yields (50–99 %).

    11. Cholesterol Conjugates

      C-3β-Tethered Functional Cholesterol Conjugates by Nitrile Oxide Alkyne Cycloaddition (NOAC) (pages 2522–2532)

      Virginie Algay, Justine O'Sullivan and Frances Heaney

      Article first published online: 24 FEB 2014 | DOI: 10.1002/ejoc.201301822

      Thumbnail image of graphical abstract

      Nitrile oxide alkyne cycloaddition (NOAC) chemistry ― a tool for attaching cholesterol to biomolecules or groups capable of bioreporting.

    12. Diamantane Diammonium Salts

      Design, Synthesis, and X-ray Structural Analyses of Diamantane Diammonium Salts: Guests for Cucurbit[n]uril (CB[n]) Hosts (pages 2533–2542)

      Marina Šekutor, Krešimir Molčanov, Liping Cao, Lyle Isaacs, Robert Glaser and Kata Mlinarić-Majerski

      Article first published online: 19 FEB 2014 | DOI: 10.1002/ejoc.201301844

      Thumbnail image of graphical abstract

      Diam-4,9-di(NMe3I) (left) was readily prepared, whereas corresponding Diam-1,6-di(NMe3I) (right) could not be obtained even under strong reaction conditions. Stereochemical analysis suggests that the cause is very severe steric non-bonding cis-1,3-diaxial type H···H interactions between the “axial”-type NMe3 group and neighboring “axial” proton neighbors that cannot be alleviated by skeletal distortion.

    13. Organocatalysis

      Syntheses of a Flobufen Metabolite and Dapoxetine Based on Enantioselective Allylation of Aromatic Aldehydes (pages 2543–2548)

      Filip Hessler, Aleš Korotvička, David Nečas, Irena Valterová and Martin Kotora

      Article first published online: 24 FEB 2014 | DOI: 10.1002/ejoc.201301899

      Thumbnail image of graphical abstract

      The enantioselective allylation of an aromatic aldehyde to give the corresponding homoallylic alcohol was the key step in the syntheses of a flobufen metabolite and dapoxetine. In the first case, the homoallylic moiety was converted into a chiral five-membered lactone ring. In the second case, it was transformed into a chiral 1,3-amino alcohol moiety.

    14. Glycoconjugates

      Synthesis of glyco-Fused Bicyclic Compounds; Conformationally Constrained Scaffolds and Useful Polyfunctional Building Blocks (pages 2549–2556)

      Francisco Cardona, Giuseppe D'Orazio, Artur M. S. Silva, Francesco Nicotra and Barbara La Ferla

      Article first published online: 19 FEB 2014 | DOI: 10.1002/ejoc.201400028

      Thumbnail image of graphical abstract

      Bicyclic polyfunctional glycol-fused compounds have been synthesized from commercially available methyl gluco-pyranoside. These molecules, with their high chirality content, presence of an α,β-unsaturated ketone and multiple hydroxyl groups represent useful building blocks for the preparation of complex, optically pure compounds.

    15. Natural Products

      Total Synthesis and Structural Revision of (–)-Protubonine A and (–)-Protubonine B (pages 2557–2564)

      Paula Lorenzo, Rosana Álvarez and Ángel R. de Lera

      Article first published online: 19 FEB 2014 | DOI: 10.1002/ejoc.201400029

      Thumbnail image of graphical abstract

      The natural products (–)-protubonine A and (–)-protubonine B have the absolute configuration of (2R,3R,11S,15S), and this has been confirmed by total synthesis.

    16. Heterocycles

      Access to 3-Arylindoles through a Tandem One-Pot Protocol Involving Dearomatization, a Regioselective Michael Addition Reaction, and Rearomatization (pages 2565–2575)

      Santhosh Kumar Chittimalla, Chennakesavulu Bandi, Sireesha Putturu, Rajesh Kuppusamy, Kevin Christopher Boellaard, David Chu Aan Tan and Demi Ming Jie Lum

      Article first published online: 27 FEB 2014 | DOI: 10.1002/ejoc.201400079

      Thumbnail image of graphical abstract

      A non-metal mediated detour method for installing oxygenated aryls at the 3-position of indoles is described.

    17. Directed Acylation

      Palladium-Catalyzed C–H Acylation of Arenes Using Thioethers as Directing Groups (pages 2576–2583)

      Bo Xu, Wei Liu and Chunxiang Kuang

      Article first published online: 19 FEB 2014 | DOI: 10.1002/ejoc.201400096

      Thumbnail image of graphical abstract

      The direct acylation of thioethers via Pd-catalyzed C–H bond activation was described.

    18. Conformation Analysis

      Conformational Regulation of Substituted Azepanes through Mono-, Di-, and Trifluorination (pages 2584–2593)

      Alpesh Ramanlal Patel, Luke Hunter, Mohan M. Bhadbhade and Fei Liu

      Article first published online: 27 FEB 2014 | DOI: 10.1002/ejoc.201301811

      Thumbnail image of graphical abstract

      Seven-membered nitrogen heterocycles have flexible ring structures and this conformational diversity is important for their bioactivity. Here the conformational effects of fluorination, as well as hydroxylation, on an azepane model system are investigated by 1H NMR spectroscopy and computational modeling.

    19. Bioinspired Synthesis

      Feruloylbenzotriazole and Weinreb Amide as Bioinspired Building Blocks: A Reactivity Study towards O-, N-, S-, and C-Nucleophiles (pages 2594–2611)

      Bart I. Roman, Jean-Christophe Monbaliu, Laurens M. De Coen, Sigrid Verhasselt, Bart Schuddinck, Evelien Van Hoeylandt and Christian V. Stevens

      Article first published online: 5 MAR 2014 | DOI: 10.1002/ejoc.201301895

      Thumbnail image of graphical abstract

      Feruloylbenzotriazole and Weinreb amide were converted into an array of biologically relevant molecules by addition of O-, N-, S-, and C-nucleophiles. The relevance of this bioinspired approach is illustrated by the synthesis of a number of natural products or analogues, such as zingerone, (heteroaryl) chalcones, and curcuminoids.

SEARCH

SEARCH BY CITATION