Chemistry – An Asian Journal

Cover image for Vol. 5 Issue 4

April 1, 2010

Volume 5, Issue 4

Pages 641–959

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Community Report
    6. Focus Reviews
    7. Communications
    8. Full Papers
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    1. Cover Picture: Meso-Substituted Liquid Porphyrins (Chem. Asian J. 4/2010) (page 641)

      Agnieszka Nowak-Król, Dorota Gryko and Daniel T. Gryko

      Version of Record online: 30 MAR 2010 | DOI: 10.1002/asia.201090008

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      Porphyrins and phthalocyanines tend to form stacks and aggregates owing to their planar nature, which eventually results in low solubility, high crystallinity, and high melting point. D. T. Gryko et al. report the synthesis and characterization of a homologous series of porphyrins with very low melting points. Within this series, the first liquid (and not liquid crystal) porphyrins at room temperature are observed. This discovery not only opens the way to design porphyrins possessing such substituents in optical limiting devices but also allows its broader use in other applications where liquidity or very high solubility are desirable. For further details, turn to their Full Paper on page 904 ff.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Community Report
    6. Focus Reviews
    7. Communications
    8. Full Papers
    9. Preview
  3. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Community Report
    6. Focus Reviews
    7. Communications
    8. Full Papers
    9. Preview
  4. Community Report

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Community Report
    6. Focus Reviews
    7. Communications
    8. Full Papers
    9. Preview
    1. JSPS Asian Core Program: Cutting-Edge Organic Chemistry in Asia and IUPAC Strategic Planning for a New East and Southeast Asian Network for Organic Chemistry (pages 660–666)

      Minoru Isobe, Toshio Nishikawa and Pauline Chiu

      Version of Record online: 30 MAR 2010 | DOI: 10.1002/asia.201000137

      JSPS Asian Core Program: Cutting-Edge Organic Chemistry in Asia and IUPAC Strategic Planning for a New East and Southeast Asian Network for Organic Chemistry

  5. Focus Reviews

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Community Report
    6. Focus Reviews
    7. Communications
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    1. Natural Products

      Discovery and Syntheses of “Superbug Challengers”—Platensimycin and Platencin (pages 668–703)

      Kalanidhi Palanichamy and Krishna P. Kaliappan

      Version of Record online: 5 MAR 2010 | DOI: 10.1002/asia.200900423

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      Averting a crisis: Discovery of the new class of antibiotics platensimycin and platencin that work with a novel mode of action is a turning point in antibiotic research. A comprehensive account on the demand for new antibiotics and the synthetic and biological aspects of platensimycin, platencin, and their analogues and congeners is provided in this Focus Review.

    2. Total Sythesis

      New Approaches to the Total Synthesis of the Bryostatin Antitumor Macrolides (pages 704–754)

      Karl J. Hale and Soraya Manaviazar

      Version of Record online: 30 MAR 2010 | DOI: 10.1002/asia.200900634

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      The bryostatin antitumor macrolides continue to capture the imagination and attention of chemists and life scientists alike, not only for their novel biological properties, but also for their challenging structures and the opportunities they provide for doing high-level organic synthesis. In this Focus Review, we will highlight some of the more significant developments that have taken place in the bryostatin total synthesis field over the period 2001–2009.

  6. Communications

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Community Report
    6. Focus Reviews
    7. Communications
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    1. Oxidation Catalysts

      A Structural Model for HPO42− Binding to Co in a Water Oxidation Catalyst (pages 756–758)

      Lisa F. McClintock and Allan G. Blackman

      Version of Record online: 8 FEB 2010 | DOI: 10.1002/asia.200900728

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      How might it bind? The X-ray structural characterization of the first example of chelated HPO42− in a mononuclear transition-metal complex provides a possible model for HPO42− bonding to CoIII in the water oxidation catalyst isolated by Kanan and Nocera.

    2. Metalloporphyrins

      Quinoneimido Complexes of a Metalloporphyrin: Isolation, X-ray Crystal Structures, and DFT Calculations (pages 759–763)

      Wai-Man Tsui, Jie-Sheng Huang, Glenna So Ming Tong, Steven C. F. Kui, Chi-Ming Che and Nianyong Zhu

      Version of Record online: 1 FEB 2010 | DOI: 10.1002/asia.200900666

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      Terminal quinoneimido complexes [RuIV(por)(NQu)(X)] (X=OEt: 1, OH: 2) were formed from the reaction of [RuVI(por)O2] with 2,6-dimethylaniline. The X-ray crystal structures of 1 feature Ru[BOND]N(quinoneimido) bond lengths of 1.787(7)–1.80(2) Å. Reaction of 2 with N-phenyl-benzene-1,4-diamine afforded bis(quinoneimido) complex [Ru(por)(NQu)(NQu′)]. DFT calculations on 3 and 4 revealed a significant effect of ‘Ru doping’ on the oligoaniline structure.

    3. Multiporphyrin Arrays

      Bithiophene–Porphyrin Hybrid Nanorings (pages 764–767)

      Kenta Osawa, Jianxin Song, Ko Furukawa, Hiroshi Shinokubo, Naoki Aratani and Atsuhiro Osuka

      Version of Record online: 28 JAN 2010 | DOI: 10.1002/asia.200900619

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      Meso-to-meso bithiophene-bridged cyclic porphyrin 3-mer, 4-mer, and 5-mer were prepared by one-pot Suzuki–Miyaura coupling reaction. The UV/Vis absorption spectra of the protonated bithiophene–porphyrin hybrid rings indicate the strong intramolecular electronic interactions between porphyrin and bithiophene units. Furthermore, ZnII complexes (see picture for example: Zn pink, N blue, S orange) were shown to serve as multicharge storage systems.

    4. Macrocyclic Compounds

      Superior Anion-Binding Properties of a Cryptand-like Oligopyrrolic Macrocycle (pages 768–772)

      Seong-Jin Hong, Jaeduk Yoo, Dae-Wi Yoon, Juyoung Yoon, Jong Seung Kim and Chang-Hee Lee

      Version of Record online: 9 FEB 2010 | DOI: 10.1002/asia.200900518

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      Recognition by strapped system: Cryptand-type calix[4]pyrrole are shown to exhibit a highly enhanced affinity towards anionic guests as compared to other reported calix[4]pyrroles (see figure). The results obtained provide some insights as to how calix[4]pyrrole-based anion receptors may be designed to achieve higher affinity and selectivity.

    5. Fluorescent Labeling

      Clickable Long-Wave “Mega-Stokes” Fluorophores for Orthogonal Chemoselective Labeling of Cells (pages 773–777)

      Krisztina Nagy, Erika Orbán, Szilvia Bősze and Péter Kele

      Version of Record online: 1 FEB 2010 | DOI: 10.1002/asia.200900477

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      Dyes that can easily be tied: The synthesis of water-soluble far-red/NIR emitting polymethine-based dyes with clickable functionalities (azide, alkyne) and their application in cell-surface labeling are presented.

    6. Friedel–Crafts Alkylation

      Recyclable Sulfonated Amorphous Carbon Catalyzed Friedel–Crafts Alkylation of Indoles with α,β-Unsaturated Carbonyl Compounds in Water (pages 778–782)

      Jimei Ma, Simon Ng, Youjun Yong, Xiao-Zhou Luo, Xin Wang and Xue-Wei Liu

      Version of Record online: 8 FEB 2010 | DOI: 10.1002/asia.200900726

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      Green practice: A sulfonated amorphous carbon-based solid acid derived from D-glucose was synthesized. It was explored for its catalytic efficiency in Friedel–Crafts reactions of indoles with various α,β-unsaturated carbonyl compounds in H2O or H2O/THF at room temperature. Moderate to excellent yields (67–96 %) were afforded. The catalyst could be recycled up to five times without any significant loss of catalytic activity.

    7. Photosensitizers

      Aptamer–Target Binding Triggered Molecular Mediation of Singlet Oxygen Generation (pages 783–786)

      Zhiwen Tang, Zhi Zhu, Prabodhika Mallikaratchy, Ronghua Yang, Kwame Sefah and Weihong Tan

      Version of Record online: 25 MAR 2010 | DOI: 10.1002/asia.200900545

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      Molecular mediation of singlet oxygen generation is demonstrated based on a newly engineered aptamer probe. Both ATP and human α-thrombin aptamers were engineered to testify to this design, and both showed that the production of singlet oxygen can be triggered and quantitatively mediated by the presence of target molecules. Moreover, both photosensitizer aptamer switch (PAS) probes showed excellent selectivity toward their targets. These results suggest that a PAS can serve as a smart photodynamic therapy agent.

    8. Molecular Recognition

      The Site-Selective Molecular Recognition of Ternary Architectures by using Supramolecular Nanoporous Networks at a Liquid–Solid Interface (pages 787–790)

      Yong-Tao Shen, Min Li, Yuan-Yuan Guo, Ke Deng, Qing-Dao Zeng and Chen Wang

      Version of Record online: 8 FEB 2010 | DOI: 10.1002/asia.200900439

      Thumbnail image of graphical abstract

      Selective holes! The tetra-acidic azobenzene (NN4A) molecules (see figure) can serve as a supramolecular nanoporous template for the accommodation of C60 and coronene molecules at the same time. Experimental results indicate that C60 and coronene molecules have obvious site-selectivity for cavities formed by NN4A.

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Community Report
    6. Focus Reviews
    7. Communications
    8. Full Papers
    9. Preview
    1. Nanomaterials

      Biomimetic Synthesis of Metal Ion-Doped Hierarchical Crystals Using a Gel Matrix: Formation of Cobalt-Doped LiMn2O4 with Improved Electrochemical Properties through a Cobalt-Doped MnCO3 Precursor (pages 792–798)

      Takao Kokubu, Yuya Oaki, Hiroaki Uchiyama, Eiji Hosono, Haoshen Zhou and Hiroaki Imai

      Version of Record online: 2 MAR 2010 | DOI: 10.1002/asia.200900494

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      A little doping! Biomimetic synthesis of the cobalt-doped MnCO3 precursor facilitated the formation of cobalt-doped LiMn2O4, which possesses hierarchical structures. The cycle performance of the cobalt-doped LiMn2O4 as a cathode material for a lithium-ion battery improved in comparison with that of the pure compound. The results indicate that both the morphology and the composition of the materials can be controlled through biomimetic processes.

    2. Microreactors

      Flash Chemistry Extensively Optimized: High-Temperature Swern–Moffatt Oxidation in an Automated Microreactor Platform (pages 799–805)

      Pieter J. Nieuwland, Kaspar Koch, Noud van Harskamp, Ron Wehrens, Jan C. M. van Hest and Floris P. J. T. Rutjes

      Version of Record online: 17 FEB 2010 | DOI: 10.1002/asia.200900705

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      Going with the flow: In a comprehensive study using microreactors, the oxidation of benzyl alcohol to benzaldehyde was optimized by simultaneously varying five reaction parameters. The optimal conditions were found at 32 ms reaction time and 70 °C. The remarkable difference with conventional conditions shows both the potency of continuous-flow chemistry as well as the urgency of a paradigm shift in the design of reactions carried out under continuous-flow conditions.

    3. Asymmetric Hydrogenation

      Chiral η6-Arene/N-Tosylethylenediamine–Ruthenium(II) Complexes: Solution Behavior and Catalytic Activity for Asymmetric Hydrogenation (pages 806–816)

      Christian A. Sandoval, Fusheng Bie, Aki Matsuoka, Yoshiki Yamaguchi, Hiroshi Naka, Yuehui Li, Koichi Kato, Noriyuki Utsumi, Kunihiko Tsutsumi, Takeshi Ohkuma, Kunihiko Murata and Ryoji Noyori

      Version of Record online: 16 MAR 2010 | DOI: 10.1002/asia.200900461

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      Degrees of separation: NMR spectra, conductivity properties, and cyclic voltammograms of [RuX{(S,S)-TsNCH(C6H5)CH(C6H5)NH2}(η6-p-cymene)] (X=TfO or Cl) as well as the diffusion constants and hydrodynamic radii and volumes of the Ru+ and TfO ions are highly influenced by the nature of solvents, indicating that the ionization of the Ru[BOND]X linkage is a key for the efficacy of asymmetric hydrogenation of aromatic ketones in alcohols.

    4. Biosensors

      Fluorescence Turn-On Sensing of Lectins with Mannose-Substituted Tetraphenylethenes Based on Aggregation-Induced Emission (pages 817–824)

      Takanobu Sanji, Kentaro Shiraishi, Mitsutaka Nakamura and Masato Tanaka

      Version of Record online: 8 FEB 2010 | DOI: 10.1002/asia.200900430

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      How to sense a Con A: A mixture of the sugar–tetraphenylethylene conjugates and concanavalin A displays an intense blue emission on agglutination, which serves as a “turn-on” fluorescent sensor for lectins. The conjugates act as a sensor for Con A, but do not sense a galactose-binding lectin, PNA. An increased sensitivity of the conjugates results upon addition of mannopyranoside substituents

    5. Antiviral Agents

      Binding of Multivalent Anionic Porphyrins to V3 Loop Fragments of an HIV-1 Envelope and Their Antiviral Activity (pages 825–834)

      Kenji Watanabe, Shigeru Negi, Yukio Sugiura, Akiko Kiriyama, Akino Honbo, Katsumi Iga, Eiichi N. Kodama, Takeshi Naitoh, Masao Matsuoka and Koji Kano

      Version of Record online: 28 JAN 2010 | DOI: 10.1002/asia.200900465

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      Unwelcomed guest: Entry of HIV-1 strains into host cells is effectively inhibited when polyvalent anionic porphyrins and their iron(III) complexes cover the cationic V3 loop region of the HIV-1 envelope (see graphic). The practical application of these porphyrins as anti-HIV drugs is investigated.

    6. Fullerenes

      Reductive Benzylation of Dimetallo Hexaaryl[70]Fullerenes on the Equatorial Region (pages 835–840)

      Takeshi Fujita, Yutaka Matsuo and Eiichi Nakamura

      Version of Record online: 8 FEB 2010 | DOI: 10.1002/asia.200900651

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      Equatorial anomaly: Chemical reduction of dimetallic hexaaryl[70]fullerene complexes followed by benzylation enables the modification of the equatorial belt line of [70]fullerene, which is generally unreactive. This method made it possible to tune the [70]fullerene π system to give new dimetallic octaaryl[70]fullerenes.

    7. Aryl Amination

      Modified [(IPr)Pd(R-acac)Cl] Complexes: Influence of the acac Substitution on the Catalytic Activity in Aryl Amination (pages 841–846)

      Nicolas Marion, Oscar Navarro, Edwin D. Stevens, Elise C. Ecarnot, Andrew Bell, Dino Amoroso and Steven P. Nolan

      Version of Record online: 5 MAR 2010 | DOI: 10.1002/asia.200900654

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      Pimp your acac: The synthesis of a series of [(IPr)Pd(R-acac)Cl] complexes, where the acac ligand on palladium has been systematically modified through terminal substitution, is reported. Investigation of their catalytic activity in cross-coupling is also presented through a comparative study in an aryl amination reaction.

    8. Oxidative Coupling

      Synthesis of Naphtho[1,8-bc]pyran Derivatives and Related Compounds through Hydroxy Group Directed C[BOND]H Bond Cleavage under Rhodium Catalysis (pages 847–851)

      Satoshi Mochida, Masaki Shimizu, Koji Hirano, Tetsuya Satoh and Masahiro Miura

      Version of Record online: 23 FEB 2010 | DOI: 10.1002/asia.200900639

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      One-step synthesis: The naphtho[1,8-bc]pyran skeleton can be found in a wide range of natural products and candidates for pharmaceuticals and organic materials. The straightforward, efficient construction of the tricyclic structure was achieved by the Rh-catalyzed oxidative coupling of 1-naphthols with alkynes by means of regioselective C[BOND]H bond cleavage directed by a hydroxy function (see scheme; R=aryl, alkyl; X=H, OMe, NHCOCF3; Y=O, NMe).

    9. TiO2 Surfaces

      Interfacial Behavior of Benzoic Acid and Phenylphosphonic Acid on Nanocrystalline TiO2 Surfaces (pages 852–858)

      Erdene-Ochir Ganbold, Yunhee Lee, Kangtaek Lee, Ohyun Kwon and Sang-Woo Joo

      Version of Record online: 12 MAR 2010 | DOI: 10.1002/asia.200900414

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      At the interface: The interfacial behavior of benzoic acid (BA; see picture, left) and phenylphosphonic acid (PPOA; right) anchored on TiO2 surfaces was studied by temperature-dependent diffuse reflectance infrared Fourier transform (DRIFT) spectroscopy and density functional theory (DFT) calculations. DRIFT spectra reveal different desorption behavior for BA and PPOA above 420 °C. DFT calculations showed that BA and PPOA adsorb on TiO2 surfaces in bidentate bridging geometry, and the adsorption of PPOA is stronger than that of BA.

    10. Fullerene Nanohybrids

      Synthesis of Poly(vinyl alcohol)/C60 and Poly(N-vinylpyrrolidone)/C60 Nanohybrids as Potential Photodynamic Cancer Therapy Agents (pages 859–868)

      Marie Hurtgen, Antoine Debuigne, Ange Mouithys-Mickalad, Robert Jérôme, Christine Jérôme and Christophe Detrembleur

      Version of Record online: 5 FEB 2010 | DOI: 10.1002/asia.200900277

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      Race for the cure: Cobalt-mediated radical polymerization (CMRP) is used for the synthesis of various hydrosoluble poly(vinyl alcohol)/C60 and poly(N-vinylpyrrolidone)/C60 nanohybrids. Preliminary studies on those nanohybrids demonstrate their potential as photosensitizers for photodynamic cancer therapy (see graphic).

    11. Sensors

      Volatile Organic Compound Sensing by Quartz Crystal Microbalances Coated with Nanostructured Macromolecular Metal Complexes (pages 869–876)

      M. Kimura, M. Sugawara, S. Sato, T. Fukawa and T. Mihara

      Version of Record online: 5 MAR 2010 | DOI: 10.1002/asia.200900333

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      Talking sense: The sensing of volatile organic compounds (VOCs; see scheme) by modifying weight-detectable quartz crystal microbalances (QCMs) with polymer brushes and sterically protected metallophthalocyanines (MPcs) is demonstrated. When the polymer brushes were loaded with sulfonated CoPcs, the sensor responses were enhanced for polar VOC vapors.

    12. Protein Recognition

      Binuclear NiII-DpaTyr Complex as a High Affinity Probe for an Oligo-Aspartate Tag Tethered to Proteins (pages 877–886)

      Akio Ojida, Sho-hei Fujishima, Kei Honda, Hiroshi Nonaka, Sho-hei Uchinomiya and Itaru Hamachi

      Version of Record online: 8 FEB 2010 | DOI: 10.1002/asia.200900362

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      A small probe for a small tag: A complementary recognition pair composed of NiII-DpaTyr (see figure) and a tri-aspartate D3 tag was developed. The optimized binding pair between the dimer of NiII-DpaTyr probe and the repeated D3 peptide tag (DDDNGDDD) showed a strong-binding affinity (Kapp=5×108 to 2×109M−1) under neutral aqueous conditions.

    13. Dendrimers

      Synthesis and Characterization of Gold-Nanoparticle-Cored Dendrimers Stabilized by Metal–Carbon Bonds (pages 887–896)

      Venugopal K. Ratheesh Kumar and Karical R. Gopidas

      Version of Record online: 22 FEB 2010 | DOI: 10.1002/asia.200900388

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      A heart of gold: Reduction of HAuCl4, phase-transferred into toluene in the presence of diazonium salt capped Fréchet-type dendrons (G1–G4), results in the formation of gold-nanoparticle-cored dendrimers (NCDs; see graphic) that have carbon–gold covalent bonds, which have been characterized by TEM, thermogravimetric analysis (TGA), and IR, UV, and NMR spectroscopy.

    14. Immobilized Catalysts

      Preparation and Characterization of Chiral Oxazaborolidine Complex Immobilized SBA-15 and Its Application in the Asymmetric Reduction of Prochiral Ketones (pages 897–903)

      Umesh Balakrishnan, Nallamuthu Ananthi, Sakthivel Tamil Selvan, Ravindra Pal, Katsuhiko Ariga, Sivan Velmathi and Ajayan Vinu

      Version of Record online: 15 JAN 2010 | DOI: 10.1002/asia.200900412

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      Lining the walls: Chiral oxazaborolidine complex is immobilized in the well-ordered mesochannels of SBA-15 by a postsynthetic approach using 3-aminopropyltriethoxysilane as a reactive surface modifier. These catalysts are used for the enantioselective reduction of aromatic prochiral ketone. The activity of the chiral complex immobilized SBA-15 heterogeneous catalyst is comparable with that of the homogeneous catalyst.

    15. Porphyrins

      Meso-Substituted Liquid Porphyrins (pages 904–909)

      Agnieszka Nowak-Król, Dorota Gryko and Daniel T. Gryko

      Version of Record online: 16 MAR 2010 | DOI: 10.1002/asia.200900693

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      Melting porphyrins! Porphyrins bearing four 3,4,5-trialkoxyphenyl substituents have very low melting points. Indeed, porphyrins bearing twelve C10 and C11 alkyl chains turned out to be liquid at room temperature! These are the first liquid (and not liquid crystal) porphyrins. Their differential scanning calorimetry distinctly showed, in most of cases, only one phase transition.

    16. Positive Triazoles

      Alkylations of N4-(4-Pyridyl)-3,5-di(2-pyridyl)-1,2,4-triazole: First Observation of Room-Temperature Rearrangement of an N4-Substituted Triazole to the N1 Analogue (pages 910–918)

      Jonathan A. Kitchen, David S. Larsen and Sally Brooker

      Version of Record online: 12 MAR 2010 | DOI: 10.1002/asia.200900485

      Thumbnail image of graphical abstract

      A cool change: Alkylation of the title ligand with benzyl bromide or methyl iodide under relatively mild conditions led in some cases to unexpected rearrangement products (see picture; N blue, C gray). Reaction with excess methyl iodide in dichloromethane at room temperature resulted in the lowest reported temperature for an N4 to N1 rearrangement. Interestingly, when the solution was heated at reflux, was doubly methylated.

    17. Biosensors

      Electrografted Poly(N-mercaptoethyl acrylamide) and Au Nanoparticles-Based Organic/Inorganic Film: A Platform for the High-Performance Electrochemical Biosensors (pages 919–924)

      Limiao Li, Shoujiang Xu, Zhifeng Du, Yanfang Gao, Jinghong Li and Taihong Wang

      Version of Record online: 9 FEB 2010 | DOI: 10.1002/asia.200900490

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      Electrografting and biosensors: A high-performance electrochemical biosensor is constructed based on the combination of electrografted poly(N-succinimidyl acrylate) (PNSA) and Au nanoparticles (NPs), which in turn support the enzyme horseradish peroxidase (HRP). The biosensor shows an excellent electrocatalytic activity toward the reduction of hydrogen oxide and long-term stability.

    18. Nanomaterials

      Rare-Earth Oxide Nanostructures: Rules of Rare-Earth Nitrate Thermolysis in Octadecylamine (pages 925–931)

      Dingsheng Wang, Zhongying Wang, Peng Zhao, Wen Zheng, Qing Peng, Liqin Liu, Xueyuan Chen and Yadong Li

      Version of Record online: 10 FEB 2010 | DOI: 10.1002/asia.200900499

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      The final structure: The decomposed regularity of rare-earth nitrates in octadecylamine was studied systematically and rare-earth oxides with various nanostructures including flowers, plates, belts, and rods were obtained. The investigation of their catalytic and luminescent properties indicates potential applications of as-obtained materials.

    19. Oligomers

      X- and H-Shape Two Dimensional Conjugated Oligomers with Anthracene as the Node (pages 932–940)

      Weibin Cui, Yingying Fu, Yao Qu, Hongkun Tian, Jingping Zhang, Zhiyuan Xie, Yanhou Geng and Fosong Wang

      Version of Record online: 2 MAR 2010 | DOI: 10.1002/asia.200900591

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      Chemical letters! X- and H -shape conjugated oligomers (see figure) with anthracene as the node have been synthesized. These X- and H-mers are characterized with broader absorption spectra and narrower energy bandgaps than linear model compounds. Their 2D conjugation features were also investigated by quantum chemical calculations.

    20. Esterification

      Indium-Catalyzed Synthesis of Keto Esters from Cyclic 1,3-Diketones and Alcohols and Application to the Synthesis of Seratrodast (pages 941–945)

      Yoichiro Kuninobu, Atsushi Kawata, Taihei Noborio, Syun-ichi Yamamoto, Takashi Matsuki, Kazumi Takata and Kazuhiko Takai

      Version of Record online: 16 MAR 2010 | DOI: 10.1002/asia.200900553

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      Breathe easy! Esterification reactions from cyclic 1,3-diketones and alcohols proceed in the presence of several Lewis acids. In particular, indium(III) triflate, iron(III) triflate, and copper(II) triflate, show high catalytic activities. These reactions proceed through the carbon–carbon bond cleavage by a retro-aldol reaction. This transformation can also be applied to the synthesis of seratrodast, an antiasthmatic and eicosanoid antagonist.

    21. Cycloaddition

      Systematic Evaluation of Substituted Cyclopentadienyl Ruthenium Complexes, [(η5-C5MenH5−n)RuCl(cod)], for Catalytic Cycloadditions of Diynes (pages 946–952)

      Yoshihiko Yamamoto, Ken Yamashita and Yu Harada

      Version of Record online: 5 MAR 2010 | DOI: 10.1002/asia.200900531

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      Easy with 1,2,4! A series of η5-cyclopentadienyl ruthenium complexes, [(η5-C5MenH5−n)RuCl(cod)] (cod=1,5-cyclooctadiene), were evaluated as catalysts for the cycloaddition of 1,6-diynes with alkynes and norbornene. It was found that the complex bearing the 1,2,4-Me3Cp ligand is the most efficient catalyst in terms of the turnover number (TON) for the cycloaddition of a bulky diiododiyne with acetylene.

  8. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Community Report
    6. Focus Reviews
    7. Communications
    8. Full Papers
    9. Preview
    1. Preview: Chem. Asian J. 5/2010 (page 959)

      Version of Record online: 30 MAR 2010 | DOI: 10.1002/asia.201090011

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