Angewandte Chemie International Edition

Cover image for Vol. 49 Issue 15

April 1, 2010

Volume 49, Issue 15

Pages 2639–2801

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
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    1. Cover Picture: 1H DOSY Spectra of Ligands for Highly Enantioselective Reactions—A Fast and Simple NMR Method to Optimize Catalytic Reaction Conditions (Angew. Chem. Int. Ed. 15/2010) (page 2639)

      Katrin Schober, Evelyn Hartmann, Hongxia Zhang and Ruth M. Gschwind

      Article first published online: 23 MAR 2010 | DOI: 10.1002/anie.201000866

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      A fast and easy DOSY screening of ligands that affords high enantioselectivities in catalysis allows the aggregation trends of their transition-metal complexes to be predicted. In their Communication on page 2794 ff., R. Gschwind and co-workers present the first aggregation study of selected phosphoramidites and their complexes. This method is useful for catalyst optimization as no knowledge of the complex structure is necessary and the temperature range applicable to the desired catalytic reaction can be quickly determined.

  2. Inside Cover

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
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    1. Inside Cover: Imaging MoS2 Nanocatalysts with Single-Atom Sensitivity (Angew. Chem. Int. Ed. 15/2010) (page 2640)

      Christian Kisielowski, Quentin M. Ramasse, Lars P. Hansen, Michael Brorson, Anna Carlsson, Alfons M. Molenbroek, Henrik Topsøe and Stig Helveg

      Article first published online: 16 MAR 2010 | DOI: 10.1002/anie.201000960

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      Atoms at work!MoS2–based nanocatalysts are used for the hydrodesulfurization processes in oil refineries. In their Communication on page 2708 ff., S. Helveg and co-workers demonstrate how the nanocatalysts can be imaged with single-atom sensitivity by using recent advances in high-resolution transmission electron microscopy and that the atomic arrangement of the nanocatalysts can be visualized. Picture courtesy of P. Møller and S. Nygaard, Haldor Topsøe A/S.

  3. Graphical Abstract

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
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    1. Graphical Abstract: Angew. Chem. Int. Ed. 15/2010 (pages 2643–2651)

      Article first published online: 31 MAR 2010 | DOI: 10.1002/anie.201090043

  4. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
    11. Preview
  5. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
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    1. Comprehensive Organic Name Reactions and Reagents. By Zerong Wang. (pages 2659–2660)

      Lukas Hintermann

      Article first published online: 31 MAR 2010 | DOI: 10.1002/anie.201000292

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      John Wiley & Sons, Hoboken 2009. 3824 pp., hardcover € 489.00.—ISBN 978-0471704508

  6. Highlights

    1. Top of page
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    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
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    1. Polymerization Catalysis

      Exploitation of a Chain-End-Control Mechanism for the Synthesis of Alternating Copolymers (pages 2662–2663)

      Jean-François Carpentier

      Article first published online: 5 MAR 2010 | DOI: 10.1002/anie.200906974

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      Smart catalysts for new materials: A syndiospecific yttrium catalyst that operates by a chain-end-control mechanism enabled the highly alternating ring-opening polymerization of a mixture of two different enantiomerically pure 4-substituted β-propiolactones of opposite absolute configuration (see scheme). This strategy offers access to original sequentially controlled poly(β-hydroxyalkanoate)s.

    2. Polymer Carriers

      Triggering Release of Encapsulated Cargo (pages 2664–2666)

      Angus P. R. Johnston, Georgina K. Such and Frank Caruso

      Article first published online: 5 MAR 2010 | DOI: 10.1002/anie.200906840

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      Specific stimuli can be used to trigger the release of cargo encapsulated in polymer carriers in applications ranging from drug delivery to catalysis. Current approaches can be categorized in two classes: application of an external stimulus, such as light, and exploitation of environmental changes, such as chemical and enzymatic degradation (see picture).

  7. Minireview

    1. Top of page
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    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
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    1. Asymmetric Catalysis

      Asymmetric Organocatalysis with Sulfones (pages 2668–2679)

      Martin Nielsen, Christian Borch Jacobsen, Nicole Holub, Marcio Weber Paixão and Karl Anker Jørgensen

      Article first published online: 5 MAR 2010 | DOI: 10.1002/anie.200906340

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      Sulfone groups play a significant role in asymmetric organocatalysis, which has become a powerful tool for the synthesis of optically active compounds. Sulfones have become important substrates in organocatalysis because of their ability to generate both nucleophilic and electrophilic reaction partners, and because they serve as a precursor to many functional groups (see scheme; E=electrophile).

  8. Review

    1. Top of page
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    4. Graphical Abstract
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    1. Proteomics/Metabolomics

      Natural Products and Their Biological Targets: Proteomic and Metabolomic Labeling Strategies (pages 2680–2698)

      Thomas Böttcher, Maximilian Pitscheider and Stephan A. Sieber

      Article first published online: 23 MAR 2010 | DOI: 10.1002/anie.200905352

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      A marked profile: Various methods have been developed in the field of proteomics and metabolomics in recent years to understand the action and function of proteins and small metabolites in organisms. These methods enable the identification of the targets of natural products in complex proteomes, the characterization of protein activity, and the determination of the function of specific metabolites.

  9. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
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    1. DNA Templates

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      DNA-Origami-Directed Self-Assembly of Discrete Silver-Nanoparticle Architectures (pages 2700–2704)

      Suchetan Pal, Zhengtao Deng, Baoquan Ding, Hao Yan and Yan Liu

      Article first published online: 16 MAR 2010 | DOI: 10.1002/anie.201000330

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      Noble decoration: DNA origami nanostructures (purple) were utilized as spatially addressable templates to organize noble-metal nanoparticles of silver (yellow balls) and gold (red ball) into well-defined discrete architectures (see examples of nanostructure designs and TEM images of the assembled structures).

    2. Molecular Recognition

      Supramolecular Interactions at the Inorganic–Organic Interface in Hybrid Nanomaterials (pages 2705–2707)

      Huibiao Liu, Zicheng Zuo, Yanbing Guo, Yongjun Li and Yuliang Li

      Article first published online: 9 MAR 2010 | DOI: 10.1002/anie.200906614

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      Pickpocket: Perylene can be detected by inorganic–organic nanomaterials comprising ZnO nanorods (gray cylinder) and perylene diimide derivatives (red rectangle). Intercalation of perylene (yellow rectangle) in a molecular pocket at the inorganic–organic interface results in fluorescence quenching of the three components with a detection limit as low as 10−12M.

    3. High-Resolution Microscopy

      Imaging MoS2 Nanocatalysts with Single-Atom Sensitivity (pages 2708–2710)

      Christian Kisielowski, Quentin M. Ramasse, Lars P. Hansen, Michael Brorson, Anna Carlsson, Alfons M. Molenbroek, Henrik Topsøe and Stig Helveg

      Article first published online: 15 MAR 2010 | DOI: 10.1002/anie.200906752

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      Close up: The atomic arrangement of industrial-style MoS2 nanocatalysts can be scrutinized by using single-atom-sensitive electron microscopy (see picture). This technique, which provides an excellent agreement between simulation and experiment, allows element detection in compound materials and permits the type and the concentration of the catalytically important edge sites to be estimated.

    4. Nanotechnology

      Gold Nanorods in Photodynamic Therapy, as Hyperthermia Agents, and in Near-Infrared Optical Imaging (pages 2711–2715)

      Wen-Shuo Kuo, Chich-Neng Chang, Yi-Ting Chang, Meng-Heng Yang, Yi-Hsin Chien, Shean-Jen Chen and Chen-Sheng Yeh

      Article first published online: 16 MAR 2010 | DOI: 10.1002/anie.200906927

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      The best of three worlds: Gold nanorods coated with poly(styrene-alt-maleic acid) (see picture; pink), the photosensitizer indocyanine green (black), and antibodies (green “Y”) serve not only as photodynamic therapy and hyperthermia agents to destroy malignant cells, but they also act as optical contrast agents to simultaneously to monitor cells by imaging in the near-IR region.

    5. Vinylborane Complexes

      η3-Vinylborane Complexes of Platinum and Nickel: Borataallyl- and Alkyl/Borataalkene-Like Coordination Modes (pages 2716–2719)

      Kristopher B. Kolpin and David J. H. Emslie

      Article first published online: 15 MAR 2010 | DOI: 10.1002/anie.200906931

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      Anyone for pi? The vinylborane PhHC[DOUBLE BOND]CH-B(C6F5)2 reacts with zero-valent Group 10 transition-metal precursors to form η3-vinylborane complexes. The platinum tri-tert-butylphosphine complex exhibits an η3-borataallyl-like coordination mode whereas the nickel bis(triphenylphosphine) complex tends towards alkyl/borataalkene coordination.

    6. Nanobiotechnology

      Isothermal Detection of DNA by Beacon-Assisted Detection Amplification (pages 2720–2723)

      Ashley R Connolly and Matt Trau

      Article first published online: 15 MAR 2010 | DOI: 10.1002/anie.200906992

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      Not bad at all: A simple biological circuit composed of two integrated molecular switches was developed for the detection and amplification of a specific nucleic acid in a biological extract. The nucleic acid is recognized by a molecular beacon, then a DNA polymerase and nicking endonuclease are used to rapidly amplify the signal for sensitive detection of the nucleic acid.

    7. Drug Delivery

      Synthetic Skin-Permeable Proteins Enabling Needleless Immunization (pages 2724–2727)

      Yongzhuo Huang, Yoon Shin Park, Cheol Moon, Allan E. David, Hee Sun Chung and Victor C. Yang

      Article first published online: 15 MAR 2010 | DOI: 10.1002/anie.200906153

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      More than skin-deep: Synthetic skin-permeable antigens are constructed by conjugation of the cell-penetrating low-molecular-weight protamine (LMWP) peptide to protein antigens through cleavable disulfide bonds. Such artificial antigens can penetrate the stratum corneum barrier (see picture), thereby sensitizing the skin immune system to elicit robust immune responses.

    8. Tandem Reactions

      Diastereo- and Enantioselective Catalytic Tandem Michael Addition/Mannich Reaction: Access to Chiral Isoindolinones and Azetidines with Multiple Stereocenters (pages 2728–2731)

      Shengmei Guo, Yinjun Xie, Xinquan Hu, Chungu Xia and Hanmin Huang

      Article first published online: 9 MAR 2010 | DOI: 10.1002/anie.200907320

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      Michael and Mannich cooperate: A rapid and reliable approach to highly functionalized chiral isoindolindone and azetidine derivatives, possessing multiple contiguous stereogenic centers, has been achieved (see scheme).

    9. Bioorganic Chemistry

      Amide-to-Ester Substitution Allows Fine-Tuning of the Cyclopeptide Conformational Ensemble (pages 2732–2737)

      Tommaso Cupido, Jan Spengler, Javier Ruiz-Rodriguez, Jaume Adan, Francesc Mitjans, Jaume Piulats and Fernando Albericio

      Article first published online: 8 MAR 2010 | DOI: 10.1002/anie.200907274

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      Without affecting the overall 3D structure, amide-to-ester backbone substitution (or ester scan) exerts a pronounced influence on the conformational equilibrium of the RGD cyclopeptide cilengitide and its derivatives (see figure; RGD=Arg-Gly-Asp). The appropriate substitution, which stabilized the receptor-complementary conformations, improved the biological activity of this integrin antagonist.

    10. Quadruplex Sensors

      DNA-Templated Synthesis of Trimethine Cyanine Dyes: A Versatile Fluorogenic Reaction for Sensing G-Quadruplex Formation (pages 2738–2742)

      Kamel Meguellati, Girish Koripelly and Sylvain Ladame

      Article first published online: 12 MAR 2010 | DOI: 10.1002/anie.201000291

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      A healthy glow: Fluorogenic peptide nucleic acids (PNAs) functionalized with indoline derivatives are used to specifically sense G-quadruplex formation. Upon hybridization of both PNAs to the single-stranded flanking arms of quadruplex DNA (see scheme), the synthesis of a trimethine cyanine dye is templated. Dye formation can be detected by the appearance of a characteristic fluorescence signal.

    11. Multicomponent Reactions

      General and Efficient Copper-Catalyzed Three-Component Coupling Reaction towards Imidazoheterocycles: One-Pot Synthesis of Alpidem and Zolpidem (pages 2743–2746)

      Natalia Chernyak and Vladimir Gevorgyan

      Article first published online: 8 MAR 2010 | DOI: 10.1002/anie.200907291

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      Three is not a crowd: A method for the construction of imidazopyridine, imidazoquinoline, and imidazoisoquinoline frameworks has been developed. The synthetic utility of this method was demonstrated in a highly efficient one-pot synthesis of the drugs alpidem and zolpidem (see scheme).

    12. Cascade Reactions

      A Triple-Aldol Cascade Reaction for the Rapid Assembly of Polyketides (pages 2747–2749)

      Brian J. Albert and Hisashi Yamamoto

      Article first published online: 12 MAR 2010 | DOI: 10.1002/anie.200907076

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      Triple play: The title reaction of 1 with simple aldehydes gives 3,5,7-trisilyloxy aldehydes in high yields and diastereoselectivities with extremely low catalyst loading (see scheme). Iodobenzene facilitates the third aldol reaction by apparently acting as a Lewis base towards the silyl catalyst. Tf=trifluoromethanesulfonyl.

    13. Asymmetric Catalysis

      Chemoenzymatic Synthesis and Application of Bicyclo[2.2.2]octadiene Ligands: Increased Efficiency in Rhodium-Catalyzed Asymmetric Conjugate Additions by Electronic Tuning (pages 2750–2754)

      Yunfei Luo and Andrew J. Carnell

      Article first published online: 12 MAR 2010 | DOI: 10.1002/anie.200907033

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      On your bi(cycle)ke! A series of 1,4-dimethyl bicyclic [2.2.2] diene ligands with tunable substitution at the bridge positions was accessed using a lipase resolution and a high yielding six step sequence (see scheme). The bridgehead methyl groups improve efficiency allowing less aryl boronic acid to be used in the title reaction.

    14. Lipidlike Ionic Liquids

      The Fluid-Mosaic Model, Homeoviscous Adaptation, and Ionic Liquids: Dramatic Lowering of the Melting Point by Side-Chain Unsaturation (pages 2755–2758)

      Samuel M. Murray, Richard A. O'Brien, Kaila M. Mattson, Christopher Ceccarelli, Richard E. Sykora, Kevin N. West and James H. Davis Jr.

      Article first published online: 8 MAR 2010 | DOI: 10.1002/anie.200906169

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      Defying conventional wisdom: Ionic liquids (ILs) with long, unsaturated alkyl appendages (see top structure) defy established trends that link long ion-bound alkyl groups to higher melting points. The new ILs are also less viscous than a saturated standard (see bottom structure) at the same temperature. These features parallel those that underpin homeoviscous adaptation in certain organisms and are indirectly supportive of a fluid-mosaic-like nanoscale character.

    15. Metallacycles

      Synthesis and Characterization of Rhenabenzenes (pages 2759–2762)

      Ka Chun Poon, Liangxian Liu, Tongxun Guo, Juan Li, Herman H. Y. Sung, Ian D. Williams, Zhenyang Lin and Guochen Jia

      Article first published online: 12 MAR 2010 | DOI: 10.1002/anie.200907014

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      Do the Maca-Rhena: Although there are many known stable metallabenzenes that contain a late transition metal, there are no examples of the direct observation of metallabenzenes that contain an early or middle transition metal. The isolation and structural characterization of air-stable rhenabenzenes 1 and 2 (see scheme) are reported.

    16. Dendrimers

      High-Generation Second-Order Nonlinear Optical (NLO) Dendrimers: Convenient Synthesis by Click Chemistry and the Increasing Trend of NLO Effects (pages 2763–2767)

      Zhong'an Li, Wenbo Wu, Qianqian Li, Gui Yu, Li Xiao, Yunqi Liu, Cheng Ye, Jingui Qin and Zhen Li

      Article first published online: 9 MAR 2010 | DOI: 10.1002/anie.200906946

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      Click it in: Forth and fifth generation dendrimers (see structure), bearing 30 and 62 azobenzene chromophore moieties, respectively, are conveniently prepared in satisfactory yields through a combination of divergent and convergent approaches by using the powerful Sharpless “click” reaction.

    17. Decarboxylative C[BOND]H Activation

      Decarboxylative C[BOND]H Cross-Coupling of Azoles (pages 2768–2771)

      Fengzhi Zhang and Michael F. Greaney

      Article first published online: 16 MAR 2010 | DOI: 10.1002/anie.200906921

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      Côte d'Azole: The title reaction demonstrates the use of diverse oxazoles 2 as suitable substrates in cross-coupling reactions with azole-5-carboxylic acids 1 under palladium catalysis in the presence of copper carbonate. The reaction is successful for the synthesis of a range of bis(azole)s, and has been applied to the convergent synthesis of challenging poly azoles (dcpe=bis(dicyclohexylphosphino)ethane, DMSO=dimethyl sulfoxide, M.S.=molecular sieves).

    18. Phase-Transfer Catalysis

      Reversal of Enantioselectivity by Tuning the Conformational Flexibility of Phase-Transfer Catalysts (pages 2772–2776)

      Ming-Qing Hua, Han-Feng Cui, Lian Wang, Jing Nie and Jun-An Ma

      Article first published online: 12 MAR 2010 | DOI: 10.1002/anie.200906814

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      Towards perfect asymmetric catalysis: When binol-derived N-spiro quaternary ammonium salts were used as phase-transfer catalysts in the conjugate addition of nitroalkanes to chalcones and its analogues, an intriguing reversal of enantioselectivity was observed. Novel chiral catalysts have been designed and synthesized (see structure).

    19. Doped Nanostructures

      Diluted Magnetic Semiconductor Nanowires Prepared by the Solution–Liquid–Solid Method (pages 2777–2781)

      Zhen Li, Lina Cheng, Qiao Sun, Zhonghua Zhu, Mark J. Riley, Muhsen Aljada, Zhenxiang Cheng, Xiaolin Wang, Graeme R. Hanson, Shizhang Qiao, Sean C. Smith and Gao Qing (Max) Lu

      Article first published online: 5 MAR 2010 | DOI: 10.1002/anie.200907021

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      Wiry frame: Manganese-doped cadmium selenide (Mn-CdSe) colloidal nanowires (see picture) exhibit ferromagnetism and good conductivity without any changed to their optical properties. The nanowires are synthesized by a novel solution–liquid–solid approach that offers a low-cost route towards magnetically active quantum wires with excellent potential applications in electronics, photonics, and spintronics.

    20. Homogeneous Catalysis

      Ruthenium(IV) Complexes Featuring P,O-Chelating Ligands: Regioselective Substitution Directly from Allylic Alcohols (pages 2782–2785)

      Basker Sundararaju, Mathieu Achard, Bernard Demerseman, Loic Toupet, Gangavaram V. M. Sharma and Christian Bruneau

      Article first published online: 12 MAR 2010 | DOI: 10.1002/anie.200907034

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      Branching out: A new ruthenium(IV) complex (1), containing a P,O-chelating ligand, is an efficient precatalyst for regioselective allylations starting from various allylic alcohol derivatives.

    21. Hypervalent Iodine Compounds

      A Versatile and Highly Reactive Polyfluorinated Hypervalent Iodine(III) Compound (pages 2786–2789)

      Sascha Schäfer and Thomas Wirth

      Article first published online: 16 MAR 2010 | DOI: 10.1002/anie.200907134

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      Hyper-reactive: A highly reactive, fully fluorinated hypervalent iodine reagent (see formula) mediates new transformations (e.g. the one-pot conversion of sulfides to sulfoximines) and serves as a stoichiometric oxidant in well-established reactions (e.g. C–C bond cleavage and the conversion of alcohols into aldehydes).

    22. N-Heterocyclic Carbenes

      Functionalized 4-Aminoquinolines by Rearrangement of Pyrazole N-Heterocyclic Carbenes (pages 2790–2793)

      Andreas Schmidt, Niels Münster and Andrij Dreger

      Article first published online: 12 MAR 2010 | DOI: 10.1002/anie.200905436

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      Thermal decarboxylation of 1-phenylpyrazolium-3-carboxylates from the mesomeric betaine class of substances leads to pyrazole-N-heterocyclic carbenes, which immediately rearrange to multiply substituted 4-aminoquinolines (see scheme). These species are of interest for the synthesis of heterocycles and pharmacologically active compounds.

    23. Catalyst Optimization

      1H DOSY Spectra of Ligands for Highly Enantioselective Reactions—A Fast and Simple NMR Method to Optimize Catalytic Reaction Conditions (pages 2794–2797)

      Katrin Schober, Evelyn Hartmann, Hongxia Zhang and Ruth M. Gschwind

      Article first published online: 23 MAR 2010 | DOI: 10.1002/anie.200907247

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      DOSY awakening: The aggregation trends of phosphoramidite transition-metal complexes, which can catalyze highly enantioselective reactions, can be predicted by a DOSY NMR screening of the free ligands (see picture). This method is valuable for catalyst optimization as no structural knowledge of the complexes is required.

  10. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
    11. Preview
    1. You have free access to this content
      Preview: Angew. Chem. Int. Ed. 16/2010 (page 2801)

      Article first published online: 31 MAR 2010 | DOI: 10.1002/anie.201090045

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