European Journal of Organic Chemistry

Cover image for Vol. 2013 Issue 29

October 2013

Volume 2013, Issue 29

Pages 6459–6732

  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
      Recent Advances in Phthalocyanine-Based Sensitizers for Dye-Sensitized Solar Cells (Eur. J. Org. Chem. 29/2013)

      Maria-Eleni Ragoussi, Mine Ince and Tomás Torres

      Version of Record online: 9 OCT 2013 | DOI: 10.1002/ejoc.201390082

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      The cover picture shows in an illustrative manner, the progress in the field of phthalocyanine-sensitized solar cells in the last decade. A boy holds one of the first phthalocyanines that appeared in the field of dye-sensitized solar cells (DSSCs) under the sun and manages to light a small lamp, while he looks stunned at the girl holding one of the most recent analogues, which, when illuminated, gives her the power to function several electric towers. Talking numbers, rational molecular design of phthalocyanines over the years has led to DSSCs with overall conversion efficiencies in the order of 6 %. Details of the recent advances in the field are presented in the Microreview by T. Torres et al. on page 6475 ff. The authors would like to acknowledge Alexandros Ragoussis for the illustration of this cover.

  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. Light Harvesting

      Recent Advances in Phthalocyanine-Based Sensitizers for Dye-Sensitized Solar Cells (pages 6475–6489)

      Maria-Eleni Ragoussi, Mine Ince and Tomás Torres

      Version of Record online: 28 AUG 2013 | DOI: 10.1002/ejoc.201301009

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      Phthalocyanine-based sensitizers have proved to be important candidates in the pursuit of efficient organic dyes for incorporation in dye-sensitized solar cells, due to their attractive physical and optical properties. Rational design of the macrocycles has brought significant progress in the field, with the efficiencies reaching 6 %. Here we describe the latest advances in Pc-based DSSCs.

  5. Short Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Directed C–H Iodination

      Metal-Free Directed ortho C–H Iodination: Synthesis of 2′-Iodobiaryl-2-carbonitriles (pages 6491–6495)

      Satinath Sarkar, Manoranjan Jana and Tadigoppula Narender

      Version of Record online: 5 SEP 2013 | DOI: 10.1002/ejoc.201300584

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      Metal-free directed ortho C–H iodination of biaryl-2-carbonitriles is efficiently performed in good yields by using bis(pyridine)iodonium(I) tetrafluoroborate (IPy2BF4, Barluenga's reagent) and HBF4·OEt2.

    2. Dehydroxylation

      Iridium-Catalyzed Direct Dehydroxylation of Alcohols (pages 6496–6500)

      Jian-Lin Huang, Xi-Jie Dai and Chao-Jun Li

      Version of Record online: 17 SEP 2013 | DOI: 10.1002/ejoc.201301293

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      Iridium-catalyzed direct dehydroxylation of alcohols with hydrazine is developed through a combination of the oxidation of alcohols and Wolff–Kishner reduction. This protocol is simple to perform and highly efficient for a series of primary alcohols, especially benzylic and allylic ones.

    3. Fluorination

      Chiral N-Fluorodibenzenesulfonimide Analogues for Enantioselective Electrophilic Fluorination and Oxidative Fluorination (pages 6501–6505)

      Chuan-Le Zhu, Mayaka Maeno, Fa-Guang Zhang, Taiki Shigehiro, Takumi Kagawa, Kosuke Kawada, Norio Shibata, Jun-An Ma and Dominique Cahard

      Version of Record online: 3 SEP 2013 | DOI: 10.1002/ejoc.201300956

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      The design, synthesis, and application of de novo chiral fluorinating agents as analogues of popular N-fluorodibenzenesulfonimide (NFSI) are presented. The fluorination step by means of elemental fluorine is explored. Enantioselective fluorination is demonstrated in cyclic β-keto esters and in the synthesis of BMS-204352 (up to 86 % ee). Oxidative aminofluorination is also examined.

    4. Trifluoromethylated Heterocycles

      Enantioselective Synthesis of 5-Trifluoromethyl-2-isoxazolines and Their N-Oxides by [Hydroxy(tosyloxy)iodo]benzene-Mediated Oxidative N–O Coupling (pages 6506–6509)

      Hiroyuki Kawai, Satoshi Okusu, Etsuko Tokunaga and Norio Shibata

      Version of Record online: 11 SEP 2013 | DOI: 10.1002/ejoc.201301096

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      Biologically attractive trifluoromethyl-2-isoxazoline N-oxides were synthesized in good yields by the [hydroxy(tosyloxy)iodo]benzene-mediated oxidative N–O coupling of β-trifluoromethyl β-hydroxy ketoximes. This is the first synthesis of 5-trifluoromethyl-2-isoxazoline N-oxides, and this method provides an alternative for the enantioselective synthesis of antiparasitic 5-trifluoromethyl-2-isoxazolines.

    5. Tetrasubstituted Olefins

      A Synthetic Approach to Tetrasubstituted Alkenes: Using β-Carbonyl Benzothiazol-2-yl Sulfones as Electrophiles (pages 6510–6513)

      Song Ou, Chun-Ru Cao, Min Jiang and Jin-Tao Liu

      Version of Record online: 9 SEP 2013 | DOI: 10.1002/ejoc.201301021

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      A mild and efficient olefination method based on the modified Julia olefination reaction is developed. The reaction of β-carbonyl benzothiazol-2-yl sulfones with nucleophiles allows the formation of β-alkoxy sulfones, which undergo facile Smiles rearrangement and spontaneous elimination to afford tetrasubstituted enynes and cyanoalkenes, respectively.

    6. Tandem Reactions

      Chemoselective Carbozincation of Cyclopropene for C–C Bond Formation and Cleavage in a Single Operation (pages 6514–6518)

      Kohei Endo, Takeo Nakano, Shuhei Fujinami and Yutaka Ukaji

      Version of Record online: 11 SEP 2013 | DOI: 10.1002/ejoc.201301026

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      The tandem carbozincation of cyclopropene, C–C bond cleavage of the cyclopropylzinc intermediate, and allylation of an unactivated hydrazone proceeds in a single operation. The reaction gives sterically congested amines diastereoselectively.

    7. Natural Product Synthesis

      Total Synthesis of the Antifungal Natural Product Mollisin (pages 6519–6524)

      Sonja Schwolow, Horst Kunz, Joachim Rheinheimer and Till Opatz

      Version of Record online: 23 AUG 2013 | DOI: 10.1002/ejoc.201301088

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      No successful synthetic attempt has been reported for the fungal fungicide mollisin. Herein, the ipso substitution of an arylstannane permits the introduction of the characteristic dichloroacetyl moiety and the completion of its first total synthesis. Starting from commercially available 2,6-dimethyl-γ-pyrone, the synthesis requires nine linear steps and provides the natural polyketide in an overall yield of 9 %.

    8. Mukaiyama Aldol Reaction

      Gallium(III) Triflate Catalyzed Diastereoselective Mukaiyama Aldol Reaction by Using Low Catalyst Loadings (pages 6525–6529)

      Baptiste Plancq, Lyse Carole Justafort, Mathieu Lafantaisie and Thierry Ollevier

      Version of Record online: 5 SEP 2013 | DOI: 10.1002/ejoc.201301100

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      A diastereoselective Mukaiyama aldol reaction was performed under mild conditions with a low loading of the gallium(III) triflate catalyst (down to 0.01 mol-%). The transformation proceeded efficiently to afford the corresponding β-hydroxy ketones in yields up to 92 %.

    9. C–H Activation

      Aromatic C–H Addition to Ketones: The Effect of Directing Groups (pages 6530–6534)

      Xi-Sha Zhang, Qi-Lei Zhu, Fei-Xian Luo, Guihua Chen, Xin Wang and Zhang-Jie Shi

      Version of Record online: 13 SEP 2013 | DOI: 10.1002/ejoc.201301115

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      The RhIII-catalyzed intermolecular nucleophilic addition of aromatic C–H bonds to ketones is reported. The steric hindrance of the directing group plays a vital role in promoting reactivity. A coordinating atom in the ketone is thought to stabilize the intermediate in addition to the product through coordination to the metal center and intramolecular hydrogen bonding, respectively. Cp* = C5Me5, DCE = 1,2-dichloroethane.

    10. Organocatalysis

      Electrostatic Repulsion and Hydrogen-Bonding Interactions in a Simple N-Aryl-L-valinamide Organocatalyst Control the Stereoselectivity in Asymmetric Aldol Reactions (pages 6535–6539)

      Yuya Tanimura, Kenji Yasunaga and Kaori Ishimaru

      Version of Record online: 2 SEP 2013 | DOI: 10.1002/ejoc.201301138

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      Small, simple, and flexible N-(2,6-difluorophenyl)-L-valinamide controls the stereoselectivity in asymmetric aldol and cross-aldol reactions under environmentally friendly conditions. The use of this catalyst in a cross-aldol reaction allows easy access to bioactive 3-hydroxy-3-(2-oxocyclohexyl)indolin-2-one with excellent diastereo- and enantioselectivities.

    11. Iodonium Ylides

      Wittig Reagents as Metallocarbene Precursors: In Situ Generated Monocarbonyl Iodonium Ylides (pages 6540–6544)

      Phyllis E. Ho, Jason Tao and Graham K. Murphy

      Version of Record online: 3 SEP 2013 | DOI: 10.1002/ejoc.201300954

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      Monocarbonyl iodonium ylides (MCIYs) represent a possible alternative to the use diazoketones and -esters as metallocarbene precursors. Upon treatment with iodosylbenzene, a Wittig reagent will undergo ylide transfer to generate a MCIY in situ. In the presence of transition-metal catalysts, MCIYs serve as precursors to metallocarbenes, which undergo dimerization or cyclopropanation of alkenes. tfacac = trifluoroacetylacetonate.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Polyol,Polyene Antibiotics

      Synthesis of a Cn–Cn+6 Building Block Common to Important Polyol,Polyene Antibiotics from a Divinylcarbinol by a Desymmetrizing Sharpless Epoxidation (pages 6545–6562)

      Luc Nachbauer and Reinhard Brückner

      Version of Record online: 17 SEP 2013 | DOI: 10.1002/ejoc.201300181

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      The termini of a bis(tert-butyl alkoxyacetate) have been differentiated by forming the bis-enolate and engaging one enolate in a diastereoselective [2,3]-Wittig rearrangement. A diastereo- and chemoselective iodolactonization established the stereocenter of the epoxide ring.

    2. Stereocontrolled Synthesis of a Cn–Cn+6 Building Block for the Unnatural Enantiomers of Important Polyol,Polyene Antibiotics from an Epoxy Alcohol by a Reduction/Conjugate Addition/Hydroxylation Sequence (pages 6563–6583)

      Rainer Kramer and Reinhard Brückner

      Version of Record online: 18 SEP 2013 | DOI: 10.1002/ejoc.201300182

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      A CuBr·SMe2/LiBr/LiSPh-promoted 1,4-addition of vinylmagnesium chloride to a γ-chiral α,β-unsaturated ester, obtained from a Sharpless epoxide, and an ensuing hydroxylation of the C-α position with the Davis oxaziridine has established the stereocenter of the epoxide ring.

    3. Stereocontrolled Synthesis of a Cn–Cn+7 Building Block (“Eastern Moiety”) for the Unnatural Enantiomers of Important Polyol,Polyene Antibiotics Based on a Ring-Closing Metathesis and an Aldol Addition of a Lactone Enolate (pages 6584–6600)

      Sonja B. Kamptmann and Reinhard Brückner

      Version of Record online: 17 SEP 2013 | DOI: 10.1002/ejoc.201300183

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      A dibromovinyl-substituted unsaturated δ-lactone obtained by ring-closing metathesis underwent a highly diastereoselective silyl cuprate 1,4-addition/aldolization sequence. Tamao–Fleming oxidation transformed the silyl into a hydroxy group. Alkyne formation, hydrostannylation, and N-bromosuccinimidolysis converted the dibromovinyl into a trans-bromovinyl moiety.

    4. Azulene Derivatives

      Synthesis and Electrochemical Properties of Carbocyclic and Heterocyclic Diazulenylethenes (pages 6601–6610)

      Eugenia Andreea Dragu, Simona Nica, Victorita Tecuceanu, Daniela Bala, Constantin Mihailciuc, Anamaria Hanganu and Alexandru C. Razus

      Version of Record online: 26 AUG 2013 | DOI: 10.1002/ejoc.201300354

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      Novel 1,2-di(azulen-1-yl)ethenes, having the double bond included in a five-membered carbocyclic or heterocyclic ring, were conveniently synthesized by McMurry coupling reactions. Their electrochemical properties were examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV), and the electrochemical behavior–structure relationship was established.

    5. Molecular Devices

      Oxazolone-Based Photoswitches: Synthesis and Properties (pages 6611–6618)

      Marina Blanco-Lomas, Ignacio Funes-Ardoiz, Pedro J. Campos and Diego Sampedro

      Version of Record online: 4 SEP 2013 | DOI: 10.1002/ejoc.201300641

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      A family of photoswitches is comprehensively studied. These compounds are easily synthesized and show interesting features for their use in a number of applications. They are thermally and photochemically stable, and the photostationary state can be tuned by the substituents, solvent and irradiation conditions.

    6. Dendrimers

      Synthesis and Characterization of Carbazole Dendrimers as Solution-Processed High Tg Amorphous Hole-Transporting Materials for Electroluminescent Devices (pages 6619–6628)

      Narid Prachumrak, Sukrawee Pansay, Supawadee Namuangruk, Tinnagon Kaewin, Siriporn Jungsuttiwong, Taweesak Sudyoadsuk and Vinich Promarak

      Version of Record online: 23 AUG 2013 | DOI: 10.1002/ejoc.201300757

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      Carbazole dendrimers have high glass transition temperatures and have amorphous and stable electrochemical properties. Their abilities to act as solution-processed hole-transporting layers in Alq3-based green OLEDs are superior to common hole-transporters such as NBP and TPD.

    7. Multimodal Heterometallic Complexes

      Design of Porphyrin-dota-Like Scaffolds as All-in-One Multimodal Heterometallic Complexes for Medical Imaging (pages 6629–6643)

      Antoine Eggenspiller, Clément Michelin, Nicolas Desbois, Philippe Richard, Jean-Michel Barbe, Franck Denat, Cynthia Licona, Christian Gaiddon, Amira Sayeh, Philippe Choquet and Claude P. Gros

      Version of Record online: 26 AUG 2013 | DOI: 10.1002/ejoc.201300678

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      Multimodal ligands incorporating one porphyrin moiety and one or more dota-like macrocycles in the same molecular architecture have been prepared and fully characterized. Heterometallic complexes incorporating both Gd3+ and Cu2+ ions were also prepared. Preliminary relaxivity, cytotoxicity, and MRI studies showed the complexes are very promising medical imaging agents for bimodal MRI techniques.

    8. Oligosaccharides

      A Second-Generation Tandem Ring-Closing Metathesis Cleavable Linker for Solid-Phase Oligosaccharide Synthesis (pages 6644–6655)

      Ana R. de Jong, Anne G. Volbeda, Bas Hagen, Hans van den Elst, Herman S. Overkleeft, Gijsbert A. van der Marel and Jeroen D. C. Codée

      Version of Record online: 27 AUG 2013 | DOI: 10.1002/ejoc.201301055

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      A tandem ring-closing metathesis cleavable linker system for solid-phase oligosaccharide synthesis has been developed. The linker is readily cleaved with Grubbs second-generation catalyst without alkene additives to liberate the oligosaccharides from the solid support. The linker is applied in the solid-phase synthesis of two frame-shifted hyaluronic acid fragments and a β-1,3-glucan trisaccharide.

    9. Oxidative Acylation

      Palladium-Catalyzed Direct Acylation of Ketoximes and Aldoximes from the Alcohol Oxidation Level through C–H Bond Activation (pages 6656–6665)

      Satyasheel Sharma, Minyoung Kim, Jihye Park, Mirim Kim, Jong Hwan Kwak, Young Hoon Jung, Joa Sub Oh, Youngil Lee and In Su Kim

      Version of Record online: 3 SEP 2013 | DOI: 10.1002/ejoc.201300649

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      A highly efficient palladium-catalyzed oxidative ortho-acylation of O-methyl ketoximes and O-methyl aldoximes with benzylic and aliphatic alcohols from the alcohol oxidation level is described.

    10. Allylic Substitution

      Installation of a Chiral Side Chain to a 2-Alkylidene-1-cycloalkan-1-ol Unit by Using Allylic Substitution (pages 6666–6676)

      Chao Feng and Yuichi Kobayashi

      Version of Record online: 27 AUG 2013 | DOI: 10.1002/ejoc.201300792

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      The allylic substitution of exocyclic allylic picolinates (n = 1, 2; R = Ph(CH2)2, iPr, Ph) with a ArCu(acac)MgBr reagent (Ar = Ph, p-tolyl, p-MeOC6H4, p-FC6H4, o-tolyl, o-MeOC6H4) that was derived from a 2:1 ratio of ArMgBr and Cu(acac)2 efficiently afforded the anti-SN2′ products in terms of regioselectivity (95–99 %), chirality transfer (91–99 %), and yield (71–91 %).

    11. Amino Acids

      From Aspartic Acid to Dihydropyridone-2-carboxylates: Access to Enantiopure 6-Substituted 4-Oxo- and 4-Hydroxypipecolic Acid Derivatives (pages 6677–6686)

      Huy-Dinh Vu, Jacques Renault, Loïc Toupet, Philippe Uriac and Nicolas Gouault

      Version of Record online: 23 AUG 2013 | DOI: 10.1002/ejoc.201300812

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      Starting from a protected (S)-aspartic acid, we used a gold-catalyzed cyclization to afford dihydropyridone 2-carboxylates that underwent reduction reactions to obtain various enantiopure 6-substituted 4-oxo- and 4-hydroxypipecolic acid derivatives.

    12. Oligonucleotide Synthesis

      Solution-Phase Synthesis of Short Oligo-2′-deoxyribonucleotides by Using Clustered Nucleosides as a Soluble Support (pages 6687–6693)

      Vyacheslav Kungurtsev, Jouni Laakkonen, Alejandro Gimenez Molina and Pasi Virta

      Version of Record online: 27 AUG 2013 | DOI: 10.1002/ejoc.201300864

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      A liquid-phase method for the synthesis of short oligonucleotides is described that is based on the efficient precipitation of tetrahedrally branched oligonucleotides in methanol.

    13. Organofluorine Compounds

      Diastereoselective Addition of Organomagnesium and Organolithium Reagents to Chiral Trifluoromethyl N-tert-Butanesulfinyl Hemiaminals (pages 6694–6701)

      Fabienne Grellepois, Abdelkhalek Ben Jamaa and Abdoulaye Gassama

      Version of Record online: 23 AUG 2013 | DOI: 10.1002/ejoc.201300890

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      The diastereoselective synthesis of trifluoromethylated tertiary and secondary carbinamines was performed by addition of a variety of organomagnesium or organolithium reagents onto trifluoromethyl N-tert-butanesulfinyl hemiaminals, stable analogs of the corresponding ketoimines.

    14. Total Synthesis

      The First Total Synthesis of Synparvolide C (pages 6702–6709)

      Gowravaram Sabitha, AnkiReddy Sandeep, Allu Senkara Rao and Jhillu S. Yadav

      Version of Record online: 3 SEP 2013 | DOI: 10.1002/ejoc.201300913

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      The first stereoselective total synthesis of synparvolide C has been accomplished by using an acid-catalyzed epoxide ring-opening reaction and ring-closing metathesis (RCM) as the key steps. A succession of functional group manipulations led to the preparation of the natural product, and spectral and analytical data were used to establish the absolute configuration.

    15. Enantioenriched Cyclic Compounds

      Construction of Enantioenriched Cyclic Compounds by Asymmetric Allylic Alkylation and Ring-Closing Metathesis (pages 6710–6721)

      Francesca Giacomina and Alexandre Alexakis

      Version of Record online: 23 AUG 2013 | DOI: 10.1002/ejoc.201300971

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      A new approach to highly enantioenriched cyclic compounds (up to 98 % ee) has been developed by using ω-ethylenic allylic substrates in a one-pot asymmetric allylic alkylation and ring-closing metathesis sequence. The starting compounds are synthetic equivalents of cyclic allylic substrates. The method is exemplified with both Cu and Ir catalysts, and chiral phosphoramidite ligands.

    16. RCM Reactions

      RCM Approach to Complex Polycyclic α-Hydroxy γ-Lactams: Synthesis of Indolizinones and Pyrroloazepinones (pages 6722–6732)

      Asier Gómez-SanJuan, Nuria Sotomayor and Esther Lete

      Version of Record online: 2 SEP 2013 | DOI: 10.1002/ejoc.201300889

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      The sequence of allylmagnesium chloride addition/RCM sequence using N-alkenyl-substituted imides provides mild access to indolizinone and pyrrolozepinone derivatives with an α-hydroxy-γ-lactam framework.

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