European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 22

August 2015

Volume 2015, Issue 22

Pages 4795–5021

  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
      Pheromone Bouquet of the Dried Bean Beetle, Acanthoscelides obtectus (Col.: Chrysomelidae), Now Complete (Eur. J. Org. Chem. 22/2015)

      József Vuts, Wittko Francke, Kenji Mori, Paulo H. G. Zarbin, Antony M. Hooper, Jocelyn G. Millar, John A. Pickett, Miklós Tóth, Keith Chamberlain, John C. Caulfield, Christine M. Woodcock, Armin G. Tröger, Éva Bálintné Csonka and Michael A. Birkett

      Article first published online: 22 JUL 2015 | DOI: 10.1002/ejoc.201590060

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      The cover picture shows a dried bean beetle, Acanthoscelides obtectus, on red beans with admirably round boreholes. Males produce a female-attracting sex pheromone (see gas chromatogram) consisting of methyl (2E,4Z,7Z)-2,4,7-decatrienoate (1), methyl (2E,4Z)-decadienoate (2), (3Z,6E)-α-farnesene (3), its (3E,6E) isomer (4), methyl (E,R)-2,4,5-tetradecatrienoate (5), and octadecanal (6). A blend of synthetic compounds in natural proportions, tested in biologically relevant amounts, was as attractive as the natural signal. These results will form the basis for the development of effective management tools against this economically important pest. Details are discussed in the article by M. A. Birkett et al. on 4843 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
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    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correction
  4. Microreview

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Microreview
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    8. Correction
    1. Heterocycle Synthesis

      The Aza-Achmatowicz Reaction: Facile Entry into Functionalized Piperidinones (pages 4811–4829)

      Ferdi van der Pijl, Floris L. van Delft and Floris P. J. T. Rutjes

      Article first published online: 28 MAY 2015 | DOI: 10.1002/ejoc.201500321

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      The aza-Achmatowicz reaction encompasses the oxidative rearrangement of readily accessible α-furanylamines into the corresponding piperidinones. The latter building blocks are synthetically versatile scaffolds that have been extensively used for the synthesis of bioactive compounds and natural products, rendering the aza-Achmatowicz reaction an important synthetic transformation.

  5. Short Communications

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    5. Microreview
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    8. Correction
    1. Hypervalent Iodine

      Preparation, X-ray Structure, and Reactivity of Triisopropylsilyl-Substituted Aryl­iodonium Salts (pages 4831–4834)

      Mekhman S. Yusubov, Dmitrii Yu. Svitich, Akira Yoshimura, Brent J. Kastern, Victor N. Nemykin and Viktor V. Zhdankin

      Article first published online: 2 JUL 2015 | DOI: 10.1002/ejoc.201500535

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      Aryliodonium salts bearing an extremely bulky, electron-donating triisopropylsilyl (TIPS) substituent in the phenyl ring are prepared and characterized by X-ray diffraction. Reactions of the TIPS-substituted arylodonium tosylate with bromide, azide, and thiocyanate anions predominantly afford products of nucleophilic substitution in the electron-rich aromatic ring bearing the TIPS substituent.

    2. Cu-Catalyzed Domino Reactions

      Copper-Catalyzed Domino Reactions for the Synthesis of Phenothiazines (pages 4835–4839)

      Manna Huang, Dongting Huang, Xinhai Zhu and Yiqian Wan

      Article first published online: 1 JUL 2015 | DOI: 10.1002/ejoc.201500667

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      A copper-catalyzed domino reaction consisting of the hydrolysis of benzothiazoles followed by C–S and C–N couplings for the synthesis of phenothiazines from benzothiazoles and aryl ortho-dihalides is described. The low loading of the catalyst system, mild experimental conditions, and the use of polyethylene glycol as the solvent make this synthetic approach very attractive to academia and industry.

    3. Mechanistic Organic Chemistry

      The Dual Reactivity of 5-S/5-O-Phenyl-1,4,2-oxathiazoles: A Fragmentation Pathway That Affords Nitriles in the Presence of Water (pages 4840–4842)

      Yi Wee Lim, Russell J. Hewitt and Brendan A. Burkett

      Article first published online: 2 JUL 2015 | DOI: 10.1002/ejoc.201500637

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      An unprecedented rearrangement of 5-phenyl-1,4,2-oxathiazoles bearing a C5 leaving group to nitriles in the presence of water is described.

  6. Full Papers

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

      Pheromone Bouquet of the Dried Bean Beetle, Acanthoscelides obtectus (Col.: Chrysomelidae), Now Complete (pages 4843–4846)

      József Vuts, Wittko Francke, Kenji Mori, Paulo H. G. Zarbin, Antony M. Hooper, Jocelyn G. Millar, John A. Pickett, Miklós Tóth, Keith Chamberlain, John C. Caulfield, Christine M. Woodcock, Armin G. Tröger, Éva Bálintné Csonka and Michael A. Birkett

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500196

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      The male-produced sex pheromone of the dried bean beetle Acanthoscelides obtectus consists of ethyl (E,R)-2,4,5-tetradecatrienoate, methyl (2E,4Z)-decadienoate, methyl (2E,4Z,7Z)-2,4,7-decatrienoate, octadecanal and (3Z,6E)- as well as (3E,6E)-α-farnesene. A complete blend of synthetic compounds in natural proportions was as attractive as the natural signal.

    2. Piperidine Synthesis

      Asymmetric Synthesis of δ-Chloro-β-amino-N-sulfinyl Imidates as Versatile Chiral Building Blocks for the Synthesis of 2,3-Disubstituted Piperidines (pages 4847–4859)

      Elena Semina, Filip Colpaert, Kristof Van Hecke, Norbert De Kimpe and Sven Mangelinckx

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500466

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      New δ-chloro-β-amino-N-sulfinyl-substituted imidates were synthesized by a highly anti-selective Mannich-type reaction, and were cyclized to give 2-aryl-N-sulfonylpiperidine-3-carbimidates in high yields. The latter were transformed into enantiomerically pure methyl 2-arylpiperidine-3-carboxylates and cis-3-amino-2-aryl-N-sulfonylpiperidines.

    3. Solid Luminogens

      Identifying Solid Luminogens through Gold-Catalysed Intramolecular Hydroarylation of Alkynes (pages 4860–4867)

      Aslam C. Shaikh, S. Shalini, Ramanathan Vaidhyanathan, Manoj V. Mane, Ayan Kumar Barui, Chitta Ranjan Patra, Yeduru Venkatesh, Prakriti Ranjan Bangal and Nitin T. Patil

      Article first published online: 30 JUN 2015 | DOI: 10.1002/ejoc.201500503

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      A gold-catalysed intramolecular hydroarylation approach for the synthesis of structurally novel pyrrolo-quinoxaline embedded coumarins is described. Their photophysical properties, as well as structural and theoretical investigations and application for live cell imaging, are discussed.

    4. Cyclic Imines

      Reactivity of N-Boc-Protected Amino-Ynones in the Presence of Zinc Chloride: Formation of Acetylenic Cyclic Imines and Their Palladium Complexes (pages 4868–4875)

      Huy-Dinh Vu, Jacques Renault, Thierry Roisnel, Clémence Robert, Philippe Jéhan, Nicolas Gouault and Philippe Uriac

      Article first published online: 29 JUN 2015 | DOI: 10.1002/ejoc.201500569

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      The reaction of γ- and δ-amino-ynones with ZnCl2 efficiently produced zinc complexes that were isolated as free acetylenic cyclic imines. Their ability to complex palladium was also investigated.

    5. Diversity-Oriented Synthesis

      Synthesis and Isolation of Enantiomerically Enriched Cyclopenta[b]benzofurans Based on Products from Anodic Oxidation of 2,4-Dimethylphenol (pages 4876–4882)

      Michael Mirion, Lars Andernach, Caroline Stobe, Joaquin Barjau, Dieter Schollmeyer, Till Opatz, Arne Lützen and Siegfried R. Waldvogel

      Article first published online: 25 JUN 2015 | DOI: 10.1002/ejoc.201500600

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      Starting from a simple phenol component an enantiomerically highly enriched pentacyclic spirolactone was obtained in three synthetic steps. The absolute configuration of the cyclopenta[b]benzofuran moiety with four countigous stereocenters was elucidated by combination of experimental and theoretical spectroscopy.

    6. β-Amino Acids

      Scalable Enantioselective Synthesis of Fmoc-β2-Serine and Fmoc-β2-Threonine by an Organocatalytic Mannich Reaction (pages 4883–4891)

      Daniel Meyer, Roger Marti and Dieter Seebach

      Article first published online: 18 JUN 2015 | DOI: 10.1002/ejoc.201500636

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      The scalable diastereoselective Mannich reaction of functionalized aldehydes with phenethylamine-derived iminium precursors, by activation with prolines and prolinol derivatives is reported. The new robust process allows the simple preparation of enantiomerically pure Fmoc-protected β2-serine and β2-threonine on multi-gram quantities.

    7. Bicyclization

      One-Pot Synthesis of Phenanthridinones by Using a Base-Catalyzed/Promoted Bicyclization of α,β-Unsaturated Carbonyl Compounds with Dimethyl Glutaconate (pages 4892–4899)

      Lei Li, Jia-Jia Chen, Xing-Lan Kan, Lu Zhang, Yu-Long Zhao and Qun Liu

      Article first published online: 23 JUN 2015 | DOI: 10.1002/ejoc.201500414

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      A one-step synthesis has been developed for functionalized phenanthridinones by starting from readily available acyclic α,β-unsaturated carbonyl compounds that contain a 2-aminophenyl group at the β-position or carbonyl carbon and dimethyl glutaconate. The domino reaction proceeds through an intermolecular [3+3] annulation followed by an intramolecular aza-cyclization/aromatization process.

    8. Cycloadditions

      Synthesis of Tetrahydro-1,2-oxazines and Pyrrolidines via Cycloadditions of Donor–Acceptor Cyclobutanes and Nitrosoarenes (pages 4900–4906)

      Naresh Vemula and Brian L. Pagenkopf

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500542

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      The scope of Yb(OTf)3-catalyzed [4+2] cycloaddition between donor–acceptor (DA) cyclobutanes and nitrosoarenes is extended to additional DA cyclobutanes. Also, an unexpected formation of pyrrolidine products was discovered when 50 mol-% of MgI2 was used as a Lewis acid with electron-rich nitrosoarenes.

    9. STAT3 Inhibitors

      Ureido-Pyridazinone Derivatives: Insights into the Structural and Conformational Properties for STAT3 Inhibition (pages 4907–4912)

      Fiorella Meneghetti, Stefania Villa, Daniela Masciocchi, Daniela Barlocco, Lucio Toma, Dong-Cho Han, Byoung-Mog Kwon, Naohisa Ogo, Akira Asai, Laura Legnani and Arianna Gelain

      Article first published online: 30 JUN 2015 | DOI: 10.1002/ejoc.201500599

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      The design, synthesis and biological properties of new potential STAT3 inhibitors with a pyridazinone ring, which replaces the 1,2,5-oxadiazole of previous investigated compounds, are described. A complete modeling study rationalized the results obtained and helped elucidate the structural and conformational properties needed for STAT3 inhibition.

    10. C–N Bond Formation

      CuI-Mediated α-Ketoacylation of Sulfoximines under Solvent-Free Conditions (pages 4913–4921)

      Ya Zou, Zhihong Peng, Wanrong Dong and Delie An

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500410

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      A new methodology for the construction of C–N bonds is herein reported. The reaction takes place under oxidative conditions, requires no base, ligands or solvents, and demonstrates excellent functional group compatibility. Moreover, control reactions suggest that the reaction proceeds through a dual C–H/N–H activation pathway.

    11. Fused 1,2,3-Triazoles

      Tandem Organocatalyzed Knoevenagel Condensation/1,3-Dipolar Cycloaddition towards Highly Functionalized Fused 1,2,3-Triazoles (pages 4922–4930)

      Jubi John, Joice Thomas, Nikita Parekh and Wim Dehaen

      Article first published online: 24 JUN 2015 | DOI: 10.1002/ejoc.201500459

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      The synthesis of a wide range of 5–7 membered ring fused 1,2,3-triazoles has been realized through a tandem organocatalyzed reaction.

    12. Actinorhodins

      Synthetic Studies toward Actinorhodin and γ-Actinorhodin by using a Homo-coupling Strategy: Synthesis of Hemiactinorhodin and Hemi-γ-actinorhodin (pages 4931–4938)

      Sandip V. Mulay, Amit Bhowmik and Rodney A. Fernandes

      Article first published online: 18 JUN 2015 | DOI: 10.1002/ejoc.201500510

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      A Dötz-type benzannulation/oxa-Pictet–Spengler-based synthesis of the pyranonaphthalene unit has been explored. The latter on oxidative dimerization failed to deliver the dimeric molecules, actinorhodin and -actinorhodin. However, the synthesis of hemiactinorhodin and hemi--actinorhodin was successfully achieved.

    13. Deoxyoligosaccharide Deprotection

      Reagent Control of a Birch Reduction for the Synthesis of a 2-Deoxyoligosaccharide Possessing a 1,4-Dialkylhydroquinone (pages 4939–4943)

      Sho Yamaguchi, Hiroshi Tanaka and Takashi Takahashi

      Article first published online: 18 JUN 2015 | DOI: 10.1002/ejoc.201500515

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      We have developed a versatile deprotection method for the synthesis of 2-deoxyoligosaccharides containing a 1,4-dialkylhydroquinone moiety. Birch reduction with potassium and 1,3-pentadiene followed by treatment with mCPBA (m-chloroperoxybenzoic acid) provided a fully deprotected landomycin E deoxytrisaccharide in a satisfying yield.

    14. Oxygen Heterocycles

      Cyclocarbonylative Sonogashira Reactions of 1-Ethynylbenzyl Alcohols: Synthesis of 1-Carbonylmethylene-1,3-Dihydroisobenzofurans (pages 4944–4949)

      Laura Antonella Aronica, Luca Giannotti, Giulia Tuci and Francesco Zinna

      Article first published online: 26 JUN 2015 | DOI: 10.1002/ejoc.201500539

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      A one-step synthesis of a set of functionalised dihydroisobenzofurans was accomplished through copper-free, palladium-catalysed cyclocarbonylative Sonogashira reactions between ethynylbenzyl alcohols and iodoarenes.

    15. Functionalization of (Hetero)arenes

      CF3-Carbenoid C–H Functionalization of (Hetero)arenes under Chelation-Controlled RhIII Catalysis (pages 4950–4955)

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

      Article first published online: 24 JUN 2015 | DOI: 10.1002/ejoc.201500545

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      An efficient method for the CF3-carbenoid C–H functionalization of benzenes and indoles using readily available methyl 3,3,3-trifluoro-2-diazopropionate under chelation-controlled RhIII catalysis has been developed. The reaction proceeds with high regioselectivity and allows the simultaneous introduction of CF3 and COOMe groups into the 2-position of directing-group-containing benzenes and indoles.

    16. Cascade Reaction

      Proline-Catalyzed Knoevenagel Condensation/[4+2] Cycloaddition Cascade Reaction: Application to Formal Synthesis of Averufin (pages 4956–4963)

      Haibo Tan, Xinzheng Chen, Huiyu Chen, Hongxin Liu and Shengxiang Qiu

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500559

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      A remarkable proline-catalyzed Knoevenagel condensation/[4+2] cycloaddition cascade reaction was uncovered for the construction of biologically interesting tricyclic ketal skeletons. This approach mimics a biosynthetic sequence and establishes a viable synthetic strategy for the efficient formal synthesis of averufin.

    17. Natural Product Chemistry

      Enantioselective Synthesis of Four Natural Homoisoflavonoids (pages 4964–4972)

      Yan-Chao Yu, Shijun Zhu, Xiao-Wei Lu, Yikang Wu and Bo Liu

      Article first published online: 25 JUN 2015 | DOI: 10.1002/ejoc.201500579

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      Four natural homoisoflavonoids were synthesized for the first time by using Evans' asymmetric aldol reaction to install the stereogenic center. The 1H and 13C NMR data of the synthetic samples were in agreement with the reported values, and the absolute configurations of three of the compounds were also established. Errors in previously reported NMR spectroscopic data/solvents were also revealed.

    18. Radical Alkylation

      Introduction of Ether Groups onto Electron-Deficient Nitrogen-Containing Heteroaromatics Using Radical Chemistry under Transition-Metal-Free Conditions (pages 4973–4981)

      Naoki Okugawa, Katsuhiko Moriyama and Hideo Togo

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500584

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      Electron-deficient nitrogen-containing heteroaromatics undergo thermal reaction with assorted ethers forming alkylated products in good to moderate yields under transition-metal-free conditions; their irradiation in the presence of benzoyl peroxide and crown ethers afforded corresponding lariat aza-crown ethers in good to moderate yields.

    19. Sigmatropic Rearrangements

      Removable Silyl Group as a “Masked Proton” in Oxy-2-oxonia(azonia)-Cope Rearrangement: Applications in Stereoselective Total Synthesis of Natural Macrolides (pages 4982–4989)

      Wenbo Mu, Yue Zou, Lijun Zhou, Quanrui Wang and Andreas Goeke

      Article first published online: 1 JUL 2015 | DOI: 10.1002/ejoc.201500654

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      In the presence of a Lewis acid, trimethylsilyl-substituted β,γ-unsaturated ketones and aldehydes (imines) undergo nucleophilic addition to produce zwitterionic intermediates, followed by oxy-2-oxonia(azonia)-Cope rearrangements to give homoallylic esters (amides). This protocol was applied to the total synthesis of (R)-phoracantholide I.

    20. Combinatorial Quinoline Synthesis

      Solid-Phase Friedländer Synthesis Using an Alkoxyamine Linker (pages 4990–4995)

      Kota Yamaguchi, Takeshi Noda, Toshiki Tomizawa, Eriko Kanai and Hideaki Hioki

      Article first published online: 30 JUN 2015 | DOI: 10.1002/ejoc.201500426

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      A quinoline library was prepared by combinatorial synthesis using an alkoxyamine linker. The oxime linkage formed by anchoring carbonyl compounds was highly robust under various reaction conditions. Desired quinolines were released by Friedländer reaction.

    21. Organophosphorus Chemistry

      Synthesis of a Phosphinate Analogue of the Antitumour Phospholipid Edelfosine (pages 4996–5003)

      Marios S. Markoulides and Andrew C. Regan

      Article first published online: 26 JUN 2015 | DOI: 10.1002/ejoc.201500477

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      A synthesis of a phosphinate analogue of the antitumour ether phospholipid edelfosine is described. Both phosphorus–oxygen bonds of the phosphate diester linkage in edelfosine are replaced by phosphorus–carbon bonds, in order to prevent hydrolytic cleavage. Free-radical addition and Michael-addition reactions are used to form the two phosphorus–carbon bonds.

    22. Protecting Groups

      4-(Acetylthio)-2,2-dimethyl-3-oxobutyl and 4-(tert-Butyldisulfanyl)-2,2-dimethyl-3-oxobutyl as Protecting Groups for Nucleoside 5′-Phosphoramidates Derived from L-Alanine Methyl Ester (pages 5004–5012)

      Vyankat A. Sontakke, Harri Lönnberg and Mikko Ora

      Article first published online: 24 JUN 2015 | DOI: 10.1002/ejoc.201500531

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      4-(Acetylthio)-2,2-dimethyl-3-oxobutyl- and 4-(tert-butyldisulfanyl)-2,2-dimethyl-3-oxobutyl-protected nucleoside 5′-phosphoramidates are deprotected to give diester-like nucleoside 5′-phosphoramidate in the presence and absence of enzyme or glutathione at pH = 7.5 and 37.0 °C.

    23. Polycycles

      Synthesis of Polycycles by Single or Double Domino Nucleophilic Substitution/Diels–Alder Reaction (pages 5013–5020)

      Pelayo Camps, David Lozano and Mercè Font-Bardia

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500601

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      A short access to complex polycycles by domino nucleophilic substitution/Diels–Alder cycloaddition

  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

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