Chemistry – An Asian Journal

Cover image for Vol. 2 Issue 9

September 3, 2007

Volume 2, Issue 9

Pages 1055–1191

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Focus Review
    6. Full Papers
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    1. Cover Picture: A DFT Study on the Mechanism of Rh2II,II-Catalyzed Intramolecular Amidation of Carbamates (Chem. Asian J. 9/2007) (page 1055)

      Xufeng Lin, Cunyuan Zhao, Chi-Ming Che, Zhuofeng Ke and David Lee Phillips

      Version of Record online: 27 AUG 2007 | DOI: 10.1002/asia.200790025

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      Singlet or triplet? That is the question asked by C.-M. Che and co-workers for the way dirhodium tetracarboxylates catalyze intramolecular C[BOND]H bond amidation. These reactions, which involve nitrene insertion, are developing into an important alternative to classical methods of C[BOND]N bond formation for building functionalized amines. Both metal–phenyliodinane and metal–nitrene intermediates have been suggested to be responsible for nitrene delivery, and concerted insertion via a singlet nitrenoid or radical recombination via a triplet nitrenoid may be feasible pathways in C[BOND]N bond formation. For the answer, turn to their Full Paper on page 1101 ff.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Focus Review
    6. Full Papers
    7. Preview
  3. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Focus Review
    6. Full Papers
    7. Preview
  4. Focus Review

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Focus Review
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    1. Ring-Rearrangement Metathesis (pages 1064–1082)

      Nicole Holub and Siegfried Blechert

      Version of Record online: 16 JUL 2007 | DOI: 10.1002/asia.200700072

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      Anything's possible: Ring-rearrangement metathesis is highly efficient for constructing complex structures. An examination of the driving forces, limits, and scope of this reaction, as well as recent applications and future perspectives, is presented in this Focus Review. Ns=nitrobenzenesulfonyl.

  5. Full Papers

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    3. Graphical Abstract
    4. News
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    1. Multirotations of (Anilinium)([18]Crown-6) Supramolecular Cation Structure in Magnetic Salt of [Ni(dmit)2] (pages 1083–1090)

      Sadafumi Nishihara, Tomoyuki Akutagawa, Daisuke Sato, Sadamu Takeda, Shin-ichiro Noro and Takayoshi Nakamura

      Version of Record online: 3 AUG 2007 | DOI: 10.1002/asia.200700010

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      Round and round we go: (Anilinium)-([18]crown-6) dynamic supramolecular cations undergo different modes of rotation in the solid state. The 180° flip-flop motion of anilinium and the rotation of [18]crown-6 were confirmed from solid-state NMR spectra. Multimolecular rotations of different motional freedoms were also observed simultaneously.

    2. A Two-Dimensional Coordination Compound as a Zinc Ion Selective Luminescent Probe for Biological Applications (pages 1091–1100)

      Koushik Dhara, Santanu Karan, Jagnyeswar Ratha, Partha Roy, Goutam Chandra, Mario Manassero, Biswanath Mallik and Pradyot Banerjee

      Version of Record online: 16 JUL 2007 | DOI: 10.1002/asia.200700152

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      A zinc sink: A selective fluorescent sensor for the detection of Zn2+ in cultured living cells (B16F10 mouse melanoma and A375 human melanoma) and rat hippocampal slices can be found in a 2D coordination compound that dissociates in solution to produce a metalloligand that binds with Zn2+. This system is highly selective and suitable for biological applications.

    3. A DFT Study on the Mechanism of Rh2II,II-Catalyzed Intramolecular Amidation of Carbamates (pages 1101–1108)

      Xufeng Lin, Cunyuan Zhao, Chi-Ming Che, Zhuofeng Ke and David Lee Phillips

      Version of Record online: 21 AUG 2007 | DOI: 10.1002/asia.200700068

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      Alone yet together: DFT calculations elucidate the catalytic process of a dirhodium tetracarboxylate catalyzed intramolecular C[BOND]H bond-amidation reaction. Out of six reaction pathways that involve a metal–nitrene complex, the singlet concerted pathway that produces the product with retention of chirality at C is predicted to be the predominant one.

    4. Identification of Inhibitors for Mycobacterial Protein Tyrosine Phosphatase B (MptpB) by Biology-Oriented Synthesis (BIOS) (pages 1109–1126)

      Ivan R. Corrêa Jr., Andrea Nören-Müller, Horst-Dieter Ambrosi, Sven Jakupovic, Krishna Saxena, Harald Schwalbe, Markus Kaiser and Herbert Waldmann

      Version of Record online: 8 AUG 2007 | DOI: 10.1002/asia.200700125

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      Inspired by nature: The first class of inhibitors for a mycobacterial phosphatase required for survival of the bacterium in the host is developed by means of biology-oriented synthesis. The highly substituted indolo[2,3-a]quinolizidines are produced by a combination of a vinylogous Mannich–Michael reaction and phosgene- or acid-mediated ring closure.

    5. gem-Dihalocyclopropanes as Building Blocks in Natural-Product Synthesis: Enantioselective Total Syntheses of ent-Erythramine and 3-epi-Erythramine (pages 1127–1136)

      Pauline C. Stanislawski, Anthony C. Willis and Martin G. Banwell

      Version of Record online: 10 AUG 2007 | DOI: 10.1002/asia.200700155

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      A radical synthesis: The nonnatural enantiomer, (−)-1, of erythramine can be prepared thus: simultaneous forming of the A and C rings by AgI-induced electrocyclic ring opening of the key intermediate 2 followed by trapping of the resulting π-allyl cation by the tethered nitrogen atom ([RIGHTWARDS ARROW]3). The derived iodide 4 undergoes radical addition/elimination to form the B ring. Alloc=allyloxycarbonyl.

    6. Formation of [Ru(bpy)3]2+-Containing Microstructures Induced by Electrostatic Assembly and Their Application in Solid-State Detection of Electrochemiluminescence (pages 1137–1141)

      Xuping Sun, Yan Du, Lixue Zhang, Shaojun Dong and Erkang Wang

      Version of Record online: 6 JUL 2007 | DOI: 10.1002/asia.200700002

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      An electrifying attraction: [Ru(bpy)3]2+-containing microstructures can be formed through electrostatic assembly of [Ru(bpy)3]2+ and [Fe(CN)6]3− by direct mixing of aqueous [Ru(bpy)3]Cl2 and K3[Fe(CN)6]. Both the molar ratio and concentration of the reactants strongly influence the formation of these microstructures, which exhibit excellent electrochemiluminescent behavior.

    7. Cascade Triple-Aldehyde Addition of 1,2,3,4-Tetrakis(pinacolatoboryl)but- 2-ene: Stereoselective Synthesis of 2,3-Bis(alkylidene)alkane-1,5-diols (pages 1142–1149)

      Masaki Shimizu, Katsuhiro Shimono and Tamejiro Hiyama

      Version of Record online: 2 AUG 2007 | DOI: 10.1002/asia.200700153

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      Melting pot: Triple-aldehyde addition of 1,2,3,4-tetraborylbut-2-ene upon heating at 100 °C gives 2,3-bis(alkylidene)alkane-1,5-diols as a single stereoisomer. The cascade reaction, which occurs in situ during preparation of the tetraborylbutene reagent, involves sequential conversion of four C[BOND]B bonds into two C[BOND]C bonds and one C[DOUBLE BOND]C bond. B=pinacolatoboryl.

    8. Organocatalytic Asymmetric Nitroaldol Reaction: Cooperative Effects of Guanidine and Thiourea Functional Groups (pages 1150–1160)

      Yoshihiro Sohtome, Nobuko Takemura, Keisuke Takada, Rika Takagi, Toshitsugu Iguchi and Kazuo Nagasawa

      Version of Record online: 16 JUL 2007 | DOI: 10.1002/asia.200700145

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      Helping each other: The guanidine–thiourea heterobifunctional compound 1 catalyzes diastereo- and enantioselective nitroaldol reactions at a chiral reaction interface. Addition of KI is crucial for inhibiting the retro-nitroaldol reaction and achieving high asymmetric induction. Bn=benzyl.

    9. exo-Selective Asymmetric Diels–Alder Reaction Catalyzed by Diamine Salts as Organocatalysts (pages 1161–1165)

      Taichi Kano, Youhei Tanaka and Keiji Maruoka

      Version of Record online: 19 JUL 2007 | DOI: 10.1002/asia.200700122

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      It's cool to be different: The axially chiral diamine (R)-1 was designed and used successfully with p-TsOH⋅H2O as an organocatalyst in the Diels–Alder reaction of cyclopentadiene with α,β-unsaturated aldehydes. Although the Diels–Alder reaction of such compounds is inherently endo selective, (R)-1 exhibits unprecedented levels of exo selectivity. Ts=toluenesulfonyl.

    10. Synthesis of Optically Active P-Chiral and Optically Inactive Oligophosphines (pages 1166–1173)

      Yasuhiro Morisaki, Yuko Ouchi, Kensuke Naka and Yoshiki Chujo

      Version of Record online: 19 JUL 2007 | DOI: 10.1002/asia.200700095

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      Like Ps in a pod: Optically active oligophosphines with chiral phosphorus atoms and their corresponding optically inactive counterparts can be synthesized by a step-by-step oxidative-coupling reaction. Their properties depend on the enantiomeric purity as well as the oligomer chain length.

    11. Structural Identification of DNA Adducts Derived from 3-Nitrobenzanthrone, a Potent Carcinogen Present in the Atmosphere (pages 1174–1185)

      Takeji Takamura-Enya, Masanobu Kawanishi, Takashi Yagi and Yoshiharu Hisamatsu

      Version of Record online: 21 AUG 2007 | DOI: 10.1002/asia.200700061

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      The Tropic of Cancer: 3-Nitrobenzanthrone (1) is a powerful carcinogen present in the atmosphere. With palladium-catalyzed aryl amination as a key step, several DNA adducts, the formation of which is recognized as a trigger of chemical carcinogenesis, can be synthesized. Some of these adducts are formed from the reaction of DNA with metabolic activation products of 1. dA=2′-deoxyadenosine, dG=2′-deoxyguanosine, R=H, Ac.

  6. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Focus Review
    6. Full Papers
    7. Preview
    1. Preview: Chem. Asian J. 10/2007 (page 1191)

      Version of Record online: 27 AUG 2007 | DOI: 10.1002/asia.200790028

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