Chemistry - A European Journal

Cover image for Vol. 16 Issue 47

December 17, 2010

Volume 16, Issue 47

Pages 13881–14207

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
    10. Preview
    1. Cover Picture: Aromatic Hydroxylation at a Non-Heme Iron Center: Observed Intermediates and Insights into the Nature of the Active Species (Chem. Eur. J. 47/2010) (page 13881)

      Olga V. Makhlynets and Prof. Dr. Elena V. Rybak-Akimova

      Version of Record online: 10 DEC 2010 | DOI: 10.1002/chem.201090233

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      An excellent catalyst for selective C[BOND]H oxidations with H2O2 is the complex [Fe(bpmen)(CH3CN)2][ClO4]2 (1). Until now, no intermediates have been observed in these reactions and the exact mechanism remained unclear. In their Full Paper on page 13995 ff., E. V. Rybak-Akimova and O. V. Makhlynets identified and experimentally characterized FeIII(OOH) and FeIV[DOUBLE BOND]O intermediates formed by 1 and H2O2. Detailed kinetic and mechanistic studies revealed that FeIII(OOH) produces the reactive oxidant in the rate-limiting, acid-assisted heterolytic cleavage of the O[BOND]O bond.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
    10. Preview
    1. Inside Cover: Highly Selective CO2 Capture by a Flexible Microporous Metal–Organic Framework (MMOF) Material (Chem. Eur. J. 47/2010) (page 13882)

      Haohan Wu, Randall S. Reali, David A. Smith, Dr. Michael C. Trachtenberg and Prof. Dr. Jing Li

      Version of Record online: 10 DEC 2010 | DOI: 10.1002/chem.201090234

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      A microporous metal–organic framework (MMOF) containing highly flexible one-dimensional open channels demonstrates remarkable selectivity in adsorbing carbon dioxide. The picture schematically illustrates the separation of CO2 from O2 and N2 by the MMOF under conditions that mimic industrial flue gas compositions. For more details, see the Communication by J. Li et al. on page 13951 ff.

  3. Editorials

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
    10. Preview
    1. Conference

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    2. Awards

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      The European Young Chemist Award 2010 (pages 13888–13893)

      Prof. Bruno Pignataro

      Version of Record online: 16 NOV 2010 | DOI: 10.1002/chem.201002829

  4. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
    10. Preview
  5. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
    10. Preview
  6. Minireview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
    10. Preview
    1. Receptors

      Partial Agonists and Subunit Selectivity at NMDA Receptors (pages 13910–13918)

      Rune Risgaard, Kasper B. Hansen and Prof. Rasmus P. Clausen

      Version of Record online: 13 OCT 2010 | DOI: 10.1002/chem.201001366

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      Subunit selectivity at NMDA receptors: Subunit-selective ligands for the glutamate receptors remain an area of interest, since glutamate is the major excitatory neurotransmitter in the brain and involved in a number of diseased states in the central nervous system. Few selective ligands are known, especially among the NMDA receptor class. Development of these ligands seems to be a difficult task because of the conserved region in the binding site of the NMDA receptor subunits. A scaffold developed by our group has shown potential to differentiate among the NMDA receptor subunits.

  7. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
    10. Preview
    1. Surface–Molecule Interactions

      Spontaneous Discrimination of Polycyclic Aromatic Hydrocarbon (PAH) Enantiomers on a Metal Surface (pages 13920–13924)

      Gonzalo Otero, Giulio Biddau, Dr. Taisuke Ozaki, Dr. Berta Gómez-Lor, Dr. Javier Méndez, Dr. Rubén Pérez and Dr. Jose Angel Martín-Gago

      Version of Record online: 23 NOV 2010 | DOI: 10.1002/chem.201002079

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      Surface control: Vacuum deposition of a planarized PAH (C60H30) on a Pt(111) surface induces chirality caused by the different landing side of the molecule, as shown by in situ STM images. The surface determines the landing side of individual molecules, which present different structural geometries that are shifted by about 35° (see figure). Large-scale calculations explain the atomistic mechanism of the process.

    2. Metal Oxide Films

      Molecular Mechanisms of Aluminum Oxide Thin Film Growth on Polystyrene during Atomic Layer Deposition (pages 13925–13929)

      Manjunath Puttaswamy, Kenneth Brian Haugshøj, Dr. Leif Højslet Christensen and Prof. Dr. Peter Kingshott

      Version of Record online: 12 NOV 2010 | DOI: 10.1002/chem.201001888

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      One layer at a time: A proposed growth mechanism of Al2O3 atomic layer deposition on a polystyrene surface is presented. The infiltration of trimethylaluminum and H2O precursors may result in Al2O3 growth in the polystyrene matrix (subsurface), thus forming a hybrid interface (shown in the green box) of C8H7O and C6H4O2Al ions.

    3. Asymmetric Catalysis

      Dynamic Kinetic Asymmetric Domino Oxa-Michael/Carbocyclization by Combination of Transition-Metal and Amine Catalysis: Catalytic Enantioselective Synthesis of Dihydrofurans (pages 13930–13934)

      Dr. Shuangzheng Lin, Dr. Gui-Ling Zhao, Luca Deiana, Prof. Dr. Junliang Sun, Dr. Qiong Zhang, Dr. Hans Leijonmarck and Prof. Dr. Armando Córdova

      Version of Record online: 16 NOV 2010 | DOI: 10.1002/chem.201001992

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      Into the pot: A one-pot highly chemo- and enantioselective catalytic domino oxa-Michael/carbocyclization between α,β-unsaturated aldehydes and propargylic alcohols is presented. This dynamic kinetic transformation requires a combination of transition-metal and amine catalysis to afford functionalized dihydrofurans in good to high yields and up to 99.5:0.5 e.r.

    4. Nonlinear Effects in Asymmetric Amino Acid Catalysis by Multiple Interconnected Stereoselective Catalytic Networks (pages 13935–13940)

      Dr. Ramon Rios, Dr. Patric Schyman, Dr. Henrik Sundén, Dr. Gui-Ling Zhao, Dr. Farman Ullah, Dr. Li-Jun Chen, Prof. Dr. Aatto Laaksonen and Prof. Dr. Armando Córdova

      Version of Record online: 16 NOV 2010 | DOI: 10.1002/chem.201002249

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      A fine line: The generation of significant positive nonlinear effects in asymmetric amino acid catalysis under homogeneous conditions, which can be explained by the model for cooperative catalytic stereoselective pathways, is reported. The addition of an achiral aldehyde generated the multiple interconnected stereoselective catalytic network.

    5. Natural Products

      Stereochemistry, Total Synthesis, and Biological Evaluation of the New Plant Hormone Solanacol (pages 13941–13945)

      Victor X. Chen, Dr. François-Didier Boyer, Dr. Catherine Rameau, Dr. Pascal Retailleau, Dr. Jean-Pierre Vors and Prof. Jean-Marie Beau

      Version of Record online: 24 NOV 2010 | DOI: 10.1002/chem.201002817

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      The first total synthesis of solanacol, a member of the strigolactone family, features ring-closing metathesis, enzymatic kinetic resolution, and atom-transfer radical cyclization. This defines the stereostructure of the natural product. The best hormonal activity is revealed by an acetylated derivative at O4 (see scheme).

    6. Cluster Compounds

      Facile Syntheses and Tunable Non-Linear Optical Properties of Heterothiometallic Clusters with [MS4Ag2] Units (M=Mo, W) (pages 13946–13950)

      Dr. Jinfang Zhang, Dr. Suci Meng, Prof. Dr. Yinglin Song, Huajian Zhao, Jianghua Li, Gaoju Qu, Liang Sun, Prof. Dr. Mark G. Humphrey and Prof. Dr. Chi Zhang

      Version of Record online: 16 NOV 2010 | DOI: 10.1002/chem.201001249

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      A not-so-innocent counterion: A facile synthetic method has been successfully developed to construct two unusual discrete, octanuclear planar “open” distorted-square M/S/Ag clusters {[Sr(DMAC)6]2[M4S16Ag4]} (M=Mo, W; DMAC=N,N'-dimethylacetylamide) and a unique 1D double-chain W/S/Ag cluster {[Sr(DMAC)6][W2S8Ag4I2]}n (see figure). Z-scan experiments show that {[Sr(DMAC)6]2[Mo4S16Ag4]} exhibits strong third-order non-linear optical properties and a large optical limiting capability.

    7. Microporous Materials

      Highly Selective CO2 Capture by a Flexible Microporous Metal–Organic Framework (MMOF) Material (pages 13951–13954)

      Haohan Wu, Randall S. Reali, David A. Smith, Dr. Michael C. Trachtenberg and Prof. Dr. Jing Li

      Version of Record online: 24 NOV 2010 | DOI: 10.1002/chem.201002683

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      Caught in a CO2trap: A highly flexible microporous metal–organic framework material exhibits a remarkable ability to capture and separate carbon dioxide from other small gases, such as N2, H2, CH4, CO, and O2, with separation ratios of 294, 190, 257, and 441 for CO2/N2, CO2/H2, CO2/CH4, and CO2/CO, respectively, at 0.16 atm and 25 °C, and 768 for CO2/O2 at 0.2 atm and 25 °C.

    8. Supramolecular Gels

      Versatile Supramolecular Gelling Agents: Unusual Stabilization of Physical Gels by Lithium Ions (pages 13955–13959)

      Jung-A Kim, Young-Hwan Jeong and Prof. Woo-Dong Jang

      Version of Record online: 4 NOV 2010 | DOI: 10.1002/chem.201002185

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      Stuck Li-ke glue: Oligo(ethylene oxide)-bridged bis(cyclodipeptides) exhibited remarkable enhancement of gelation ability by the addition of Li+ (see figure). By coordination of metal ions to the oligo(ethylene oxide) chain, terminal cyclodipeptides may move closer and more easily form the hydrogen-bonded-sheet structure of cyclodipeptides.

    9. Supramolecular Chemistry

      Antisymbiotic Self-Assembly and Dynamic Behavior of Metallamacrocycles with Allylic Corners (pages 13960–13964)

      Dr. Inmaculada Angurell, Dr. Montserrat Ferrer, Dr. Albert Gutiérrez, Prof. Manuel Martínez, Dr. Laura Rodríguez, Prof. Oriol Rossell and Dr. Marianne Engeser

      Version of Record online: 12 NOV 2010 | DOI: 10.1002/chem.201002605

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      Hip to be square: Tetranuclear metallamacrocycles containing Pd–allyl and either Pd(dppp) or Pt(dppp) moieties (dppp=1,3-bis(diphenylphosphino)propane) have been obtained from the selective combination of three different building blocks. The study of their unusual dynamic behavior demonstrated the equilibrium between the self-assembled supramolecules and their components (see scheme).

    10. Heterogeneous Catalysis

      Efficient and Clean Gold-Catalyzed One-Pot Selective N-Alkylation of Amines with Alcohols (pages 13965–13969)

      Lin He, Xia-Bing Lou, Ji Ni, Dr. Yong-Mei Liu, Prof. Dr. Yong Cao, Prof. Dr. He-Yong He and Prof. Kang-Nian Fan

      Version of Record online: 19 NOV 2010 | DOI: 10.1002/chem.201001848

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      Atom-efficient direct N-alkylation: An environmentally clean one-pot selective N-alkylation of amines with an equimolar amount of alcohols via a hydrogen autotransfer pathway was achieved over a titania-supported gold catalyst system in good to excellent yields without additive (see scheme).

    11. Supramolecular Assembly

      Facile Glycoenzyme Wiring to Electrode Supports by Redox-Active Biosupramolecular Glue (pages 13970–13975)

      Dr. Diego Pallarola, Nuria Queralto, Prof. Dr. Wolfgang Knoll, Dr. Omar Azzaroni and Prof. Dr. Fernando Battaglini

      Version of Record online: 12 NOV 2010 | DOI: 10.1002/chem.201001407

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      It has to be glue! The use of redox-active concanavalin A as a bifunctional building block enables the recognition-directed assembly of HRP layers on bioelectronic platforms and the communication of the prosthetic group of the enzyme to the electrode surface (see figure).

    12. Retrosynthesis

      The Handy Use of Brown’s P2-Ni Catalyst for a Skipped Diyne Deuteration: Application to the Synthesis of a [D4]-Labeled F4t-Neuroprostane (pages 13976–13980)

      Camille Oger, Dr. Valérie Bultel-Poncé, Dr. Alexandre Guy, Dr. Laurence Balas, Prof. Jean-Claude Rossi, Dr. Thierry Durand and Dr. Jean-Marie Galano

      Version of Record online: 12 NOV 2010 | DOI: 10.1002/chem.201002304

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      Brown's P2-Ni does the job: An efficient synthesis of tetradeuterated neuroprostane (see structure) has been accomplished by using an ene–diyne stereoselective deuteration strategy.

  8. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
    10. Preview
    1. Protecting Groups

      Quantifying Electronic Effects of Common Carbohydrate Protecting Groups in a Piperidine Model System (pages 13982–13994)

      Mads Heuckendorff, Dr. Christian M. Pedersen and Dr. Mikael Bols

      Version of Record online: 3 DEC 2010 | DOI: 10.1002/chem.201002313

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      Carbohydrates at arms: How great an influence protecting groups have on the reactivity of carbohydrates has been determined. The protecting groups in a “disarmed” saccharide are more than 300 times more electron withdrawing (EWD) than those in an “armed” saccharide and those of a “superarmed” saccharide are 300 times less EWD (see scheme, TBDMS=tert-butyldimethylsilyl).

    2. Aromatic Hydroxylation

      Aromatic Hydroxylation at a Non-Heme Iron Center: Observed Intermediates and Insights into the Nature of the Active Species (pages 13995–14006)

      Olga V. Makhlynets and Prof. Dr. Elena V. Rybak-Akimova

      Version of Record online: 29 NOV 2010 | DOI: 10.1002/chem.201002577

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      Iron out the rough spots: [Fe(bpmen)(CH3CN)2][ClO4]2 (1), an excellent catalyst for organic oxidations with hydrogen peroxide, is found to efficiently promote hydroxylation of benzene. This new reaction revealed mechanistic pathways in hydrogen peroxide activation with complex 1. Detailed kinetic and mechanistic studies showed that FeIII(OOH) produces the reactive species in the rate-limiting, acid-assisted heterolytic cleavage of the O[BOND]O bond in the iron–peroxo intermediate.

    3. Polymerization

      A Lutetium Allyl Complex That Bears a Pyridyl-Functionalized Cyclopentadienyl Ligand: Dual Catalysis on Highly Syndiospecific and cis-1,4-Selective (Co)Polymerizations of Styrene and Butadiene (pages 14007–14015)

      Zhongbao Jian, Shijia Tang and Prof. Dr. Dongmei Cui

      Version of Record online: 22 OCT 2010 | DOI: 10.1002/chem.201001634

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      Challenge to a dual: Under the activation of [Ph3C][B(C6F5)4], a pyridyl-functionalized cyclopentadienyl lutetium–bis(allyl) complex exhibited unprecedented dual behavior for syndiotactic (rrrr>99 %) styrene polymerization and cis-1,4-selective (99 %) butadiene polymerization.

    4. Methane Activation

      Reactivity of C1 Surface Species Formed in Methane Activation on Zn-Modified H-ZSM-5 Zeolite (pages 14016–14025)

      Jian Feng Wu, Wei David Wang, Dr. Jun Xu, Prof. Dr. Feng Deng and Prof. Dr. Wei Wang

      Version of Record online: 29 OCT 2010 | DOI: 10.1002/chem.201002258

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      Reactivity of C1surface species: Zinc methyl species, formate species, and methoxy species were identified as C1 surface species formed in methane activation on the zeolite Zn/H-ZSM-5 catalyst at T≤573 K (see graphic). We successfully isolated each surface species and investigated their chemical nature on the working catalyst by solid-state NMR spectroscopy.

    5. Photosystem II

      Hydration Preferences for Mn4Ca Cluster Models of Photosystem II: Location of Potential Substrate–Water Binding Sites (pages 14026–14042)

      Dr. Simon Petrie, Prof. Rob Stranger and Prof. Ron J. Pace

      Version of Record online: 22 OCT 2010 | DOI: 10.1002/chem.201001132

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      Water ways: Density functional calculations are reported on a set of three model structures of the Mn4Ca cluster in the water-oxidizing complex of Photosystem II (see figure). The preferred hydration sites across five oxidation states and all feasible magnetic-coupling arrangements have been explored to identify the most likely substrate–water binding sites.

    6. Metal–Organic Frameworks

      High Gas Sorption and Metal-Ion Exchange of Microporous Metal–Organic Frameworks with Incorporated Imide Groups (pages 14043–14050)

      Dr. Thazhe Kootteri Prasad, Dae Ho Hong and Prof. Myunghyun Paik Suh

      Version of Record online: 22 OCT 2010 | DOI: 10.1002/chem.201002135

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      Unprecedented oxygen capacity: Synthesis of a CuII-based metal–organic framework (MOF) with NbO-type net structure that shows high adsorption capacities for N2, H2, O2, CO2, and CH4 is reported. A similar reaction with ZnII afforded a PtS-type net. Postsynthetic metal-ion exchange of a ZnII MOF with CuII resulted in a CuII MOF with a PtS-type net that could not be obtained from direct synthesis (see figure).

    7. Organic Electronics

      A Neutral Zwitterionic Molecular Solid (pages 14051–14059)

      Dr. Abdelkrim El-Ghayoury, Cécile Mézière, Dr. Sergey Simonov, Dr. Leokadiya Zorina, Dr. Manuel Cobián, Dr. Enric Canadell, Dr. Carme Rovira, Dr. Bálint Náfrádi, Dr. Balázs Sipos, Prof. László Forró and Dr. Patrick Batail

      Version of Record online: 28 OCT 2010 | DOI: 10.1002/chem.201001875

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      Electrostatic envelope: Two neutral chemical objects with ionizable residues, one of which is a π-conjugated zwitterion, self-assemble in a two-dimensional array (see picture). It is predicted that the carriers are probably localized, yet the system is highly conducting. Although not part of the conducting network, a rattling proton deeply impinges on the collective behavior of the holes.

    8. Molecular Spin-States

      Nanoscale Self-Hosting of Molecular Spin-States in the Intermediate Phase of a Spin-Crossover Material (pages 14060–14068)

      Dr. Nicolas Bréfuel, Prof. Eric Collet, Dr. Hiroshi Watanabe, Prof. Masaaki Kojima, Prof. Naohide Matsumoto, Dr. Loic Toupet, Prof. Koichiro Tanaka and Prof. Jean-Pierre Tuchagues

      Version of Record online: 12 NOV 2010 | DOI: 10.1002/chem.201001264

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      Nanoscale self-hosting of spin-state: Thermally induced spin crossover associated with symmetry breaking yields an unprecedented long-range ordering in the intermediate (INT) phase (supercell structure of 30 molecules) of a novel molecular material based on an iron complex. A remarkable lozenge pattern is produced, including 12 predominantly high-spin (HS), 8 predominantly low-spin (LS), and 10 purely LS molecular crystallographic sites (red, purple, and blue, respectively, in figure).

    9. Frustrated Lewis Pairs

      Structure and Dynamic Features of an Intramolecular Frustrated Lewis Pair (pages 14069–14073)

      Dr. Kirill V. Axenov, Cornelia M. Mömming, Dr. Gerald Kehr, Dr. Roland Fröhlich and Prof. Dr. Gerhard Erker

      Version of Record online: 27 OCT 2010 | DOI: 10.1002/chem.201001814

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      The cyclohexylene-anellated frustrated Lewis pair was obtained by hydroboration of di(mesityl)cyclohexenylphosphine with [HB(C6F5)2]. The X-ray crystal structure analysis (see picture) revealed a puckered four-membered heterocyclic core. The compound splits dihydrogen heterolytically and adds to the C[DOUBLE BOND]O bond of phenyl isocyanate.

    10. Spiro Compounds

      Short Diastereoselective Synthesis of the C1–C13 (AB Spiroacetal) and C17–C28 Fragments (CD Spiroacetal) of Spongistatin 1 and 2 through Double Chain-Elongation Reactions (pages 14074–14082)

      Dr. Christopher L. Flowers and Prof. Dr. Pierre Vogel

      Version of Record online: 20 OCT 2010 | DOI: 10.1002/chem.201002204

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      Spiroacetal out of control! A unique and practical synthetic sequence to allow rapid access to polyketides and further to the spiroacetals derived from them is reported (see scheme). The synthesis utilizes a bidirectional Hosomi–Sakurai allylation approach around key allylsilanes in the synthesis of the AB and CD ring systems of spongistatin 1 and 2.

    11. Natural Products

      Total Syntheses of the Thiopeptides Amythiamicin C and D (pages 14083–14093)

      Dr. Carolin Ammer and Prof. Dr. Thorsten Bach

      Version of Record online: 19 OCT 2010 | DOI: 10.1002/chem.201002144

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      Cross-coupling reactions paved the way to two short syntheses of amythiamicin C (1) and D (2; see scheme). In the former synthesis, the sequence A–C–B was followed to give access to the title compound 1. In the latter synthesis, the sequence C–B–A was probed and led successfully to amythiamicin D (2) in an extremely short, but less selective, synthetic sequence.

    12. Fluorescent Molecules

      Controlling Optical Properties and Function of BODIPY by Using Asymmetric Substitution Effects (pages 14094–14105)

      Dr. Jorge Bañuelos-Prieto, Prof. Antonia R. Agarrabeitia, Dr. Inmaculada Garcia-Moreno, Dr. Iñigo Lopez-Arbeloa, Dr. Angel Costela, Dr. Lourdes Infantes, M. Eugenia Perez-Ojeda, Marta Palacios-Cuesta and Prof. María J. Ortiz

      Version of Record online: 19 OCT 2010 | DOI: 10.1002/chem.201002095

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      It's all under control: A strategy to modulate the photophysical and optical properties of BODIPYs by using asymmetric substitution effects has been developed. New asymmetric BODIPY–indene and BODIPY–fluorene dyes have been synthesized (see figure) by a simple protocol.

    13. Antioxidants

      Preparation and Investigation of Vitamin B6-Derived Aminopyridinol Antioxidants (pages 14106–14114)

      Dr. Remigiusz Serwa, Dr. Tae-gyu Nam, Dr. Luca Valgimigli, Dr. Sean Culbertson, Dr. Christopher L. Rector, Prof. Dr. Byeong-Seon Jeong, Prof. Dr. Derek A. Pratt and Prof. Dr. Ned A. Porter

      Version of Record online: 22 OCT 2010 | DOI: 10.1002/chem.201001382

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      Oxidatively stressed? Take a vitamin! An efficient and highly practical synthetic route for pyridinol-based antioxidants from vitamin B6 is reported. Antioxidant properties for new members of this family of radical scavengers have been investigated. It was discovered that these amino-pyridinols are able to not only inhibit lipid peroxidation in direct reaction with peroxyradicals but also act as co-antioxidants in the presence of vitamin E as previously reported for vitamin C (see scheme).

    14. Cyanoacetylene

      On the Trimerization of Cyanoacetylene: Mechanism of Formation of Tricyanobenzene Isomers and Laboratory Detection of Their Radio Spectra (pages 14115–14123)

      Prof. Dr. Henning Hopf, Cornelia Mlynek, Prof. Dr. Robert J. McMahon, Jessica L. Menke, Prof. Dr. Alberto Lesarri, Dr. Michael Rosemeyer and Prof. Dr. Jens-Uwe Grabow

      Version of Record online: 22 OCT 2010 | DOI: 10.1002/chem.201001648

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      The final frontier: To better understand the chemistry of cyanoacetylene—a known constituent of planetary atmospheres and interstellar space—theoretical and spectroscopic studies address the mechanism of its di- and trimerization, and provide high-resolution rotational spectra of two of the trimers: 1,2,3- and 1,2,4-tricyanobenzene (see picture).

    15. Cope Reaction

      On the Origin of Altered Diastereomeric Ratios for Anionic versus Neutral Reaction Conditions in the Oxy-Cope/Ene Reaction: An Interplay of Experiment and Computational Modeling (pages 14124–14130)

      James Hooper, Effiette L. O. Sauer, Steve Arns, Prof. Tom K. Woo and Prof. Louis Barriault

      Version of Record online: 18 OCT 2010 | DOI: 10.1002/chem.201001302

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      Carbanions at play: A sequential oxy-Cope/ene reaction, engineered to produce decalin skeleton structures for further applications in natural product synthesis, was found to give altered product distributions under anionic conditions. With DFT calculations and ab initio molecular dynamics simulations, its altered diastereoselectivity is shown to be the result of a hitherto unexpected isomerization of the enolate olefin (see scheme).

    16. Organic Light-Emitting Diodes

      Synthesis, Photophysical and Electrophosphorescent Properties of Fluorene-Based Platinum(II) Complexes (pages 14131–14141)

      Dr. Mai-Yan Yuen, Dr. Steven C. F. Kui, Dr. Kam-Hung Low, Dr. Chi-Chung Kwok, Dr. Stephen Sin-Yin Chui, Chun-Wah Ma, Nianyong Zhu and Prof. Chi-Ming Che

      Version of Record online: 19 OCT 2010 | DOI: 10.1002/chem.201001570

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      Molecularly doped PLEDs, based on poly(9-vinylcarbazole) (PVK) blended with phosphorescent fluorene-substituted cyclometalated platinum(II) complexes as dopants (see figure), exhibit excellent performance and good efficiency. A polymer light-emitting diode (PLED) containing 5 % fluorene-based platinum(II) complex shows a high current efficiency of 9.2 cd A−1 with a brightness of 3500 cd m−2.

    17. Enzyme Catalysis

      Ostensible Enzyme Promiscuity: Alkene Cleavage by Peroxidases (pages 14142–14148)

      Dr. Francesco G. Mutti, Dr. Miguel Lara, Dr. Markus Kroutil and Prof. Dr. Wolfgang Kroutil

      Version of Record online: 27 OCT 2010 | DOI: 10.1002/chem.201002265

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      Go catalytic! It has been shown that peroxidases are able to cleave selected C[DOUBLE BOND]C double bonds adjacent to activated phenyl moieties at the expense of molecular oxygen at an acidic pH as a promiscuous activity (see scheme). We could unambiguously prove that exclusively the hemin moiety present in the enzyme is responsible for this activity.

    18. Epoxidation

      Generation and Reactions of Oxiranyllithiums by Use of a Flow Microreactor System (pages 14149–14158)

      Dr. Aiichiro Nagaki, Eiji Takizawa and Prof. Dr. Jun-ichi Yoshida

      Version of Record online: 28 OCT 2010 | DOI: 10.1002/chem.201000815

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      Flow microreactor system: An integrated flow microreactor system serves as a powerful method for the stereoselective synthesis of substituted epoxides (see figure).

    19. Supramolecular Systems

      Dynamic Octopus Amphiphiles as Powerful Activators of DNA Transporters: Differential Fragrance Sensing and Beyond (pages 14159–14166)

      Dr. Javier Montenegro, Pauline Bonvin, Dr. Toshihide Takeuchi and Prof. Stefan Matile

      Version of Record online: 29 OCT 2010 | DOI: 10.1002/chem.201001352

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      Fragrant multitail amphiphiles: The in situ product of hydrophobic odorant analytes, such as muscone (see figure), and cationic multihydrazide peptide dendrons are introduced as powerful activators of DNA transporters for application indifferential sensing, cellular uptake, slow release, and fluorescent labeling.

    20. Nanostructures

      Synthesis of Ag2O Nanocrystals with Systematic Shape Evolution from Cubic to Hexapod Structures and Their Surface Properties (pages 14167–14174)

      Lian-Ming Lyu, Wei-Ching Wang and Prof. Michael H. Huang

      Version of Record online: 19 OCT 2010 | DOI: 10.1002/chem.201000563

      Thumbnail image of graphical abstract

      Shaping the future: Ag2O crystals with shapes from cubic to edge- and corner-truncated cubic, rhombicuboctahedral, edge- and corner-truncated octahedral, octahedral, and hexapod structures have been synthesized. By adjusting the reaction conditions, octapods and elongated hexapods can be prepared. Octahedra and hexapods with {111} facets are sensitive to the molecular charges in the solution.

    21. Supramolecular Chemistry

      Endogenous Arene Hydroxylation Promoted by Copper(I) Cluster Helicates (pages 14175–14180)

      Miguel Martínez-Calvo, Dr. Miguel Vázquez López, Dr. Rosa Pedrido, Dr. Ana M. González-Noya, Prof. Dr. Manuel R. Bermejo, Dr. Enrico Monzani, Prof. Dr. Luigi Casella and Dr. Lorenzo Sorace

      Version of Record online: 22 OCT 2010 | DOI: 10.1002/chem.201001285

      Thumbnail image of graphical abstract

      Capable presence: Copper(I) cluster helicates derived from a thiosemicarbazone ligand can hydroxylate the arene linker of their supporting ligand strands in the presence of O2. The kinetic studies show values of ΔH=−70 kJ mol−1, similar to those mediated by the tyrosinase enzymes.

    22. DNA Condensation

      Reversible DNA Condensation Induced by a Tetranuclear Nickel(II) Complex (pages 14181–14189)

      Xindian Dong, Prof. Dr. Xiaoyong Wang, Yafeng He, Zhen Yu, Miaoxin Lin, Changli Zhang, Jing Wang, Yajie Song, Yangmiao Zhang, Zhipeng Liu, Prof. Dr. Yizhi Li and Prof. Dr. Zijian Guo

      Version of Record online: 22 OCT 2010 | DOI: 10.1002/chem.201001457

      Thumbnail image of graphical abstract

      Nonviral vector: A tetranuclear nickel(II) complex has been designed and prepared as a nonviral vector for gene therapy. The complex can induce the condensation of DNA into nanoparticles through electrostatic interactions. The release of DNA from the compact state has been realized using the chelator ethylenediaminetetraacetic acid (EDTA) for the first time (see graphic). Along with biocompatibility and nuclease-inactivity, the complex meets most of the prerequisites for a gene vector.

    23. Lanthanide Complexes

      [Ln(binolam)3]⋅(OTf)3, a New Class of Propeller-Shaped Lanthanide(III) Salt Complexes as Enantioselective Catalysts: Structure, Dynamics and Mechanistic Insight (pages 14190–14201)

      Prof. Lorenzo Di Bari, Sebastiano Di Pietro, Dr. Gennaro Pescitelli, Dr. Fernando Tur, Javier Mansilla and Prof. José M. Saá

      Version of Record online: 18 OCT 2010 | DOI: 10.1002/chem.201001683

      Thumbnail image of graphical abstract

      A class of their own: The solution structure (see picture) and dynamics of lanthanide–binaphthol amine compounds bearing Lewis acid, Brønsted acid and Brønsted base groups are determined with paramagnetic NMR spectroscopy and circular dichroism. The complexes are active as enantioselective catalysts in the nitroaldol reaction.

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      Preview: Chem. Eur. J. 48/2010 (page 14207)

      Version of Record online: 10 DEC 2010 | DOI: 10.1002/chem.201090237

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