European Journal of Organic Chemistry

Cover image for Vol. 2012 Issue 13

May 2012

Volume 2012, Issue 13

Pages 2467–2663

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. You have free access to this content
      In Situ Dearomatisation/Alkylation of Arylphosphane Derivatives (Eur. J. Org. Chem. 13/2012)

      Marek Stankevič, Karolina Wójcik, Magdalena Jaklińska and K. Michał Pietrusiewicz

      Version of Record online: 23 APR 2012 | DOI: 10.1002/ejoc.201290030

  2. Graphical Abstract

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

      The New Age of Electrophilic Perfluoro­alk­ylation Reactions (pages 2479–2494)

      Yohan Macé and Emmanuel Magnier

      Version of Record online: 11 JAN 2012 | DOI: 10.1002/ejoc.201101535

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      New reagents! Easier access to former ones! Great choice of number of atoms of fluorine to be introduced! Catalytic methodologies improving the use of these compounds! Electrophilic perfluoroalkylation is in rapid expansion and full of promise.

  5. Short Communications

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

      HgII-Selective Fluorescent Indicator: One-Step Synthesis (pages 2495–2498)

      Seul-Bi Kim and Dong-Gyu Cho

      Version of Record online: 28 MAR 2012 | DOI: 10.1002/ejoc.201200126

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      The fluorescent indicator 2 relies on an HgII-selective reaction. The reaction involves an Hg-selective hydrolysis/decarboxylation sequence, which has not been used for any metal detection. The present fluorescent indicator requires minimal synthesis effort in a single step.

    2. Base and Electronic Effects

      Efficient and General Protocol for Sonogashira Cross-Coupling Reactions of Maleimides (pages 2499–2502)

      Agathe Souffrin, Cécile Croix and Marie-Claude Viaud-Massuard

      Version of Record online: 19 MAR 2012 | DOI: 10.1002/ejoc.201101811

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      The reactivity of maleimides in Sonogashira cross-coupling reactions was studied. The important role of the base is demonstrated, and optimized experimental conditions are described with a large variety of alkynes. The reactivity of the alkynes is also discussed. This reaction provides rapid access to a wide range of new maleimide derivatives in moderate to excellent yields.

    3. Asymmetric Conjugate Addition

      Expanding the C1-Symmetric Bicyclo[2.2.1]heptadiene Ligand Family: Highly Enantioselective Synthesis of Cyclic β-Aryl-Substituted Carbonyl Compounds (pages 2503–2507)

      Chia-Chen Liu, Damodar Janmanchi, Chun-Chih Chen and Hsyueh-Liang Wu

      Version of Record online: 23 MAR 2012 | DOI: 10.1002/ejoc.201200143

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      The highly enantioselective synthesis of cyclic β-aryl-substituted carbonyl compounds was realized through the catalytic asymmetric conjugate addition of arylboronic acids to cyclic α,β-unsaturatedcarbonyl compounds in the presence of 0.1 or 0.5 mol-% of catalyst in situ prepared from ligand 1g and [RhCl(C2H4)2]2.

    4. Sialic Acids

      Facile Diastereoselective Entry to 4β-Acylamidation of Neu5Ac2en Glycals Using Their N-Perfluoroacylated Congeners as Key Tools (pages 2508–2510)

      Paola Rota, Irene S. Agnolin, Pietro Allevi and Mario Anastasia

      Version of Record online: 22 MAR 2012 | DOI: 10.1002/ejoc.201200151

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      An efficient protocol for the 4β-acylamidation of the N-acylated glycals of Neu5Ac by using the corresponding N-perfluoroacylated congeners as key tools has been developed and applied to the synthesis of glycals combining the features of the molecules with antiviral properties.

    5. Cyclopropane Ring Opening

      Synthesis of Substituted Furans through Domino Aldol/Homo-Michael Reactions of Formylcyclopropane 1,1-Diesters with 1,3-Dicarbonyls (pages 2511–2515)

      Jilai Bao, Jun Ren and Zhongwen Wang

      Version of Record online: 27 MAR 2012 | DOI: 10.1002/ejoc.201200162

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      A Lewis acid catalyzed domino aldol/homo-Michael reaction of formylcyclopropane 1,1-diesters with 1,3-dicarbonyls has been successfully developed. This method provides efficient construction of highly functionalized furans from easily available starting materials.

    6. Fungal Metabolites

      Trichoderones A and B: Two Pentacyclic Cytochalasans from the Plant Endophytic Fungus Trichoderma gamsii (pages 2516–2519)

      Gang Ding, Hailou Wang, Li Li, Amanda Juan Chen, Lin Chen, Hong Chen, Hongwu Zhang, Xinzhong Liu and Zhongmei Zou

      Version of Record online: 21 MAR 2012 | DOI: 10.1002/ejoc.201200053

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      Trichoderones A (1) and B (2), two new cytochalasans, were isolated from the endophytic fungus Trichoderma gamsii. Trichoderone A possesses an unprecedented 7/6/6/5/5 pentacyclic system, whereas trichoderone B contains the rare 6/5/6/6/5 pentacyclic skeleton with a 12-oxatricyclo[6.3.1.02,7] moiety.

  6. Full Papers

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

      In Situ Dearomatisation/Alkylation of Arylphosphane Derivatives (pages 2521–2534)

      Marek Stankevič, Karolina Wójcik, Magdalena Jaklińska and K. Michał Pietrusiewicz

      Version of Record online: 27 MAR 2012 | DOI: 10.1002/ejoc.201200096

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      Treatment of dialkylphenylphosphane–boranes or dialkylphenylphosphane oxides with electrophiles under Birch reduction conditions selectively produces α-functionalised (cyclohexa-1,4-dien-3-yl)phosphane derivatives through an in situ dearomatisation/alkylation sequence. A slight change in the reaction conditions leads to the formation of trialkylphosphane derivatives through P–Ph bond cleavage.

    2. Fluorescent probes

      Hydroxythiazole-Based Fluorescent Probes for Fluoride Ion Detection (pages 2535–2541)

      Lorena K. Calderón-Ortiz, Eric Täuscher, Erick Leite Bastos, Helmar Görls, Dieter Weiß and Rainer Beckert

      Version of Record online: 14 MAR 2012 | DOI: 10.1002/ejoc.201200140

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      O-Silyloxy-1,3-thiazoles are used as fast-response “turn-on” probes for fluoride ion detection in polar aprotic solvents and in aqueous cetyltrimethylammonium bromide micellar medium. The high selectivity, sensitivity, and detection limit (10–7 mol L–1 in DMSO) are an advantage over other methods.

    3. Aminohydantoins

      Diversified Aminohydantoins from Ureas and Thioureas Tethered to Amides (pages 2542–2548)

      Sukumar Bepary, In Kwon Youn, Hee-Jong Lim and Ge Hyeong Lee

      Version of Record online: 16 MAR 2012 | DOI: 10.1002/ejoc.201200025

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      Intramolecular cyclization of thioureas or ureas tethered to amides afforded 2-iminohydantoins and 2-amino-1H-imidazol-4(5H)-ones in very high yields (87–100 %) regardless of the substituent (alkyls or aryls). This reaction proceeds through carbodiimides and iminium ions as intermediates.

    4. Oxidative Carbonylation

      A General Synthesis of Indole-3-carboxylic Esters by Palladium-Catalyzed Direct Oxidative Carbonylation of 2-Alkynylaniline Derivatives (pages 2549–2559)

      Bartolo Gabriele, Lucia Veltri, Raffaella Mancuso, Giuseppe Salerno and Mirco Costa

      Version of Record online: 14 MAR 2012 | DOI: 10.1002/ejoc.201200120

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      Indole-3-carboxylic esters were conveniently prepared by a carbonylative approach starting from 2-alkynylaniline derivatives. Oxidative carbonylation reactions were carried out under relatively mild conditions (100 °C under 20 atm of a 4:1 mixture of CO/air) in the presence of PdI2/KI as the catalytic system and oxygen as the only oxidant.

    5. Host–Guest Systems

      Secondary Face-to-Face 2–2′ β-Cyclodextrin Dimers Linked with Fluorescent Rigid Spacer Arms: A Cyclodextrin-Based Ratiometric Sensor for Bile Salts (pages 2560–2571)

      Manuel C. Martos-Maldonado, Indalecio Quesada-Soriano, Juan M. Casas-Solvas, Luis García-Fuentes and Antonio Vargas-Berenguel

      Version of Record online: 21 MAR 2012 | DOI: 10.1002/ejoc.201101598

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      The synthesis of a series of β-cyclodextrin dimers in which the two macrocycle units are linked through the cyclodextrin secondary sides by rigid-rod phenylene-ethynylene tethers of different length and shape is reported. Their binding and fluorescence sensing abilities toward bile salts were studied.

    6. Arylation

      Catalyst- and Base-Controlled Site-Selective sp2 and sp3 Direct Arylation of 5,7-Dimethyl-2-phenylpyrazolo[1,5-a]pyrimidine Using Aryl Bromides (pages 2572–2578)

      Ibtissam Bassoude, Sabine Berteina-Raboin, Stéphane Massip, Jean-Michel Leger, Christian Jarry, El Mokhtar Essassi and Gérald Guillaumet

      Version of Record online: 21 MAR 2012 | DOI: 10.1002/ejoc.201101833

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      In this paper, we present a new approach to control the site-selective direct C–Harylation of both sp2 and sp3 sites in5,7-dimethyl-2-phenylpyrazolo[1,5-a]pyrimidine by using aryl bromides. The desired compounds were obtained in satisfactory yields.

    7. Zinc-Mediated α-Crotylation

      High Regiocontrol in the Zinc-Mediated Crotylation of Aldehydes and Ketones: A Straightforward and Facile Approach to Linear Homoallylic Alcohols in DMPU (pages 2579–2584)

      Li-Ming Zhao, Li-Jing Wan, Hai-Shan Jin and Shu-Qing Zhang

      Version of Record online: 13 MAR 2012 | DOI: 10.1002/ejoc.201101847

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      The α-regioselective addition of crotyl bromide to carbonyl compounds was realized by the use of convenient and inexpensive zinc as the mediator with broad substrate scope in an environmentally benign solvent. Good to high yields of the corresponding α-linear homoallylic alcohols were obtained with perfect α-regioselectivity.

    8. C–C Bond Formation

      Controlled Reactions of 2,3-Allenoates with a 1,3-Diketone Catalyst Effect (pages 2585–2596)

      Zhao Fang, Chunling Fu and Shengming Ma

      Version of Record online: 13 MAR 2012 | DOI: 10.1002/ejoc.201101852

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      Ethyl (2E)-5-acyl-2-alkyl-4-aryl-6-oxohept-2-enoates have been prepared in moderate yields with an exclusive E stereoselectivity through a palladium-catalyzed hydroallylation of 2,3-allenoates and 1,3-diketones in trifluoroacetic acid. In the copper-promoted transformation, the 1,3-diketones attack the electron-deficient C=C bonds to form 4-[R–C(=O)–]-substituted 3,5-dialkyl-3-(2-oxo-2-arylethyl)furan-2(3H)-ones.

    9. Glycosidase Inhibitors

      Expeditious Racemic and Enantiodivergent Synthesis of 1-Deoxymannojirimycin and 1,4-Dideoxymannojirimycin (pages 2597–2605)

      Dina Scarpi, Laura Bartali, Andrea Casini and Ernesto G. Occhiato

      Version of Record online: 14 MAR 2012 | DOI: 10.1002/ejoc.201200022

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      The enantiodivergent synthesis of 1-deoxymannojirimycin has been realized by optical resolution of a racemic alcohol. The product was obtained in a few steps from inexpensive starting material through the formation of the diastereomeric camphanic esters followed by exhaustive deprotection. The racemic synthesis of 1,4-dideoxymannojirimycin is also reported.

    10. Cycloaddition

      [3+2] Cycloaddition of Dialkyl (E)-Hex-2-en-4-ynedioates to [60]Fullerene by Phosphane-Promoted Tandem α(δ′)-Michael Additions (pages 2606–2613)

      Shih-Ching Chuang, Jie-Cheng Deng, Fu-Wei Chan, Sheng-Yuan Chen, Wei-Je Huang, Li-Hsiang Lai and Venkatachalam Rajeshkumar

      Version of Record online: 16 MAR 2012 | DOI: 10.1002/ejoc.201200024

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      Organophosphanes promote the [3+2] cycloaddition of dialkyl (E)-hex-2-en-4-ynedioates to [60]fullerene through double α(δ′)-Michael reactions, giving a series of cyclopenteno-fullerenes 3ak bearing phosphorus ylides.

    11. Natural Product Analogues

      Total Syntheses of D-xylo- and D-arabino-Phytosphingosine Based on the Syntheses of Chiral 1,3-Oxazines (pages 2614–2620)

      Yu Mu, Tian Jin, Gun-Woo Kim, Jin-Seok Kim, Sung-Soo Kim, Yong-Shou Tian, Chang-Young Oh and Won-Hun Ham

      Version of Record online: 19 MAR 2012 | DOI: 10.1002/ejoc.201200064

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      The total syntheses of D-xylo- and D-arabino-phytosphingosine utilizing chiral oxazines are presented. We have described a new Pd0-catalyzed procedure for the stereoselective formation of the oxazine ring. The diastereoselectivity of the oxazine ring formation is predominantly controlled by temperature.

    12. Isoprostanes

      Total Synthesis of Isoprostanes Derived from Adrenic Acid and EPA (pages 2621–2634)

      Camille Oger, Valérie Bultel-Poncé, Alexandre Guy, Thierry Durand and Jean-Marie Galano

      Version of Record online: 15 MAR 2012 | DOI: 10.1002/ejoc.201200070

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      Reactive oxygen species initiate the in vivo autoxidative conversion of phospholipid-bound polyunsaturated fatty-acids. Adrenic acid, the main constituent of myelin, the “white matter” of the brain, is known to be converted into F2-dihomo-isoprostanes. We hereby present the total synthesis of the two main isomers present in vivo as well as one isomer derived from eicosapentaenoic acid.

    13. Catalytic Sequential Reactions

      Sequential Suzuki/Asymmetric Aldol and Suzuki/Knoevenagel Reactions Under Aqueous Conditions (pages 2635–2642)

      Michelangelo Gruttadauria, Lucia Anna Bivona, Paolo Lo Meo, Serena Riela and Renato Noto

      Version of Record online: 13 MAR 2012 | DOI: 10.1002/ejoc.201200092

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      The first examples of sequential Suzuki/asymmetric aldol and Suzuki/Knoevenagel reactions under aqueous conditions are reported.

    14. Aromatic Homoconjugation

      A Joint Experimental and Computational Investigation on Homoconjugated Push-Pull Chromophores Derived from 7,7-Diphenylnorbornane (pages 2643–2655)

      Noelia Herrero-García, María del Rosario Colorado Heras, María del Rosario Torres, Israel Fernández and José Osío Barcina

      Version of Record online: 15 MAR 2012 | DOI: 10.1002/ejoc.201200159

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      Electronic communication through homoconjugation between aromatic moieties can be easily controlled by changing the nature and the position of the substituents attached at the aryl rings. The electron delocalization (communication) is clearly revealed by the new homoconjugation bands in the UV/Vis spectra of the compounds studied as well as by charge transfer absorptions in push-pull systems.

    15. Homo-Oligomers

      Synthesis and Structural Characterization of Homochiral Homo-Oligomers of cis-γ-Methoxy-Substituted cis- and trans-Furanoid-β-Amino Acids (pages 2656–2663)

      Awadut G. Giri, Ganesh F. Jogdand, Pattuparampil R. Rajamohanan, Sunil K. Pandey and Chepuri V. Ramana

      Version of Record online: 16 MAR 2012 | DOI: 10.1002/ejoc.201101424

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      Structural analysis of the homo-oligomers of cis-/trans-furanoid-β-amino acid (β-FAA) oligomers having a cis-γ-methoxy group revealed that they adopt similar secondary structures like the parent cis-/trans-β-FAA oligomers without any interference from the methoxy substituent.

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