Angewandte Chemie International Edition

Cover image for Vol. 49 Issue 32

July 26, 2010

Volume 49, Issue 32

Pages 5389–5581

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Cover Picture: Design and Folding of [GluA4(OβThrB30)]Insulin (“Ester Insulin”): A Minimal Proinsulin Surrogate that Can Be Chemically Converted into Human Insulin (Angew. Chem. Int. Ed. 32/2010) (page 5389)

      Youhei Sohma, Qing-Xin Hua, Jonathan Whittaker, Michael A. Weiss and Stephen B. H. Kent

      Article first published online: 20 JUL 2010 | DOI: 10.1002/anie.201002659

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      The efficient total chemical synthesis … … of insulin has been a challenge for more than 40 years. In their Communication on page 5489 ff., Y. Sohma, S. B. H. Kent, and co-workers show that a ‘zero length’ ester-linked precursor folds as efficiently as full length proinsulin and can be simply converted into fully active insulin by saponification. (The artwork for the cover picture was prepared by D. Kent and is based on a concept by Y. Sohma).

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Inside Cover: Supported Gold and Silver Nanoparticles for Catalytic Deoxygenation of Epoxides into Alkenes (Angew. Chem. Int. Ed. 32/2010) (page 5390)

      Takato Mitsudome, Akifumi Noujima, Yusuke Mikami, Tomoo Mizugaki, Koichiro Jitsukawa and Kiyotomi Kaneda

      Article first published online: 22 JUL 2010 | DOI: 10.1002/anie.201002977

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      Silver and gold nanoparticles were shown to efficiently catalyze deoxygenation of epoxides into alkenes using alcohols as reductants, as described by K. Kaneda and co-workers in their Communication on page 5545 ff. The selectivity for the product alkenes was high and the catalysts were recyclable.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Graphical Abstract: Angew. Chem. Int. Ed. 32/2010 (pages 5393–5403)

      Article first published online: 22 JUL 2010 | DOI: 10.1002/anie.201090099

  4. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Kim Renée Dunbar (page 5408)

      Article first published online: 20 JUL 2010 | DOI: 10.1002/anie.201002716

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      „My favorite subjects at school were chemistry and mathematics. If I could have dinner with three famous scientists from history, they would be Marie Curie, Louis Pasteur, and Alfred Werner …” This and more about Kim Renée Dunbar can be found on page 5408.

  6. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. On Solar Hydrogen & Nanotechnology. Edited by Lionel Vayssieres. (page 5409)

      Thomas Nann

      Article first published online: 12 JUL 2010 | DOI: 10.1002/anie.201003557

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      John Wiley & Sons, Hoboken 2010. 704 pp., hardcover € 212.00.—ISBN 978-0470823972

  7. Highlights

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

      The Molecular Mechanism of Spider-Silk Formation (pages 5410–5412)

      Robert Silvers, Florian Buhr and Harald Schwalbe

      Article first published online: 28 JUN 2010 | DOI: 10.1002/anie.201003033

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      How spiders enmesh their prey: The NMR spectroscopic determination of the C-terminal non-repeat domain of Araneus diadematus fibroin 3 (ADF-3), a spider silk protein, was recently reported. At the same time, the X-ray structure determination of the N-terminal non-repeat domain was reported. Both structures provide key insights into fiber formation upon shear stress and pH changes, including the templating effect on fiber morphology.

    2. Fenton Polishing

      A Golden Episode Continues Fenton’s Colorful Story (pages 5413–5415)

      George Z. Chen

      Article first published online: 29 JUN 2010 | DOI: 10.1002/anie.201001449

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      Stimulating new studies using Fenton's reagent to selectively dissolve asperities and hence knock out catalytic sites on the surface of gold, may present unknown fundamental and applied opportunities; for example, modification of the surfaces of micro- and nanoparticles of gold and other metals to enhance catalytic activity, thereby making the process more affordable (see figure).

  8. Minireview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. IR Spectroscopy on Biomolecules

      Thinner, Smaller, Faster: IR Techniques To Probe the Functionality of Biological and Biomimetic Systems (pages 5416–5424)

      Kenichi Ataka, Tilman Kottke and Joachim Heberle

      Article first published online: 16 JUN 2010 | DOI: 10.1002/anie.200907114

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      Good vibes: Novel spectroscopic methodologies have been devised for the analysis of biomolecules. Recent developments in vibrational spectroscopy meet the need to measure in thinner (single monolayers), smaller (single molecules), and faster (femtoseconds) regimes. In this Minireview applications of surface techniques such as SEIRAS, SFG, and SNIM, and ultrafast techniques such as time-resolved 1D and 2D IR are described.

  9. Review

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

      Targeted Metabolomics for Biomarker Discovery (pages 5426–5445)

      William J. Griffiths, Therese Koal, Yuqin Wang, Matthias Kohl, David P. Enot and Hans-Peter Deigner

      Article first published online: 13 JUL 2010 | DOI: 10.1002/anie.200905579

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      An indication of interest: In metabolomics, questions from the areas of pathobiochemistry, systems biology, medicine, and molecular diagnostics can be addressed by using analytical chemistry and statistical data analysis. The focus of this Review is the identification and qualification of biomarkers as well as the mass spectrometric approach to targeted metabolomics.

  10. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Engineering the Genetic Code

      In Vivo Double and Triple Labeling of Proteins Using Synthetic Amino Acids (pages 5446–5450)

      Sandra Lepthien, Lars Merkel and Nediljko Budisa

      Article first published online: 23 JUN 2010 | DOI: 10.1002/anie.201000439

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      Three in one: A new method has been developed for the simultaneous in vivo incorporation of two or three different synthetic amino acids in a protein in a single expression experiment using polyauxotrophic Escherichia coli strains. The picture shows the model protein ψ-b* used and the synthetic amino acids incorporated.

    2. Frustrated Lewis Pairs

      Highly Selective Metalations of Pyridines and Related Heterocycles Using New Frustrated Lewis Pairs or tmp-Zinc and tmp-Magnesium Bases with BF3⋅OEt2 (pages 5451–5455)

      Milica Jaric, Benjamin A. Haag, Andreas Unsinn, Konstantin Karaghiosoff and Paul Knochel

      Article first published online: 7 JUL 2010 | DOI: 10.1002/anie.201002031

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      Efficient and selective: Frustrated Lewis pairs based on BF3⋅OEt2 and LiCl-complexed tmpMg or tmpZn amides (tmp=2,2,6,6-tetramethylpiperidyl) allow the efficient and regioselective metalation of various functionalized N heterocycles (see scheme for examples). Moreover, such metalations carried out in the presence or absence of BF3⋅OEt2 enable a complete switch of regioselectivity, thus allowing complementary functionalization.

    3. Photoswitchable Proteins

      Fused-Gene Approach to Photoswitchable and Fluorescent Biliproteins (pages 5456–5458)

      Juan Zhang, Xian-Jun Wu, Zhi-Bin Wang, Yu Chen, Xing Wang, Ming Zhou, Hugo Scheer and Kai-Hong Zhao

      Article first published online: 25 JUN 2010 | DOI: 10.1002/anie.201001094

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      Lighting up and changing color: Genes coding for apoprotein and chromophore biosynthesis from heme were combined in a single fused construct, thereby providing access, in vivo, to biliproteins. Persistently fluorescent biliproteins, as well as red–green photoswitchable biliproteins derived from a cyanobacteriochrome that have well-separated absorption and fluorescence maxima of the two states, were produced in E. coli.

    4. Reactive Intermediates

      Isolation of the Triplet Ground State Aminyl Diradical (pages 5459–5462)

      Przemysław J. Boratyński, Maren Pink, Suchada Rajca and Andrzej Rajca

      Article first published online: 2 JUL 2010 | DOI: 10.1002/anie.201002811

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      Spin cycle: A high-spin nitrogen-centered (aminyl) diradical with a triplet (S=1) ground state (see picture) has a large singlet-triplet energy gap (ΔEST). Effective shielding of the reactive aminyl radical centers provides stability at room temperature and maintains the planarity of the π system required for the triplet ground state and large ΔEST value. The diradical assembles in solution to form a π-dimer-like structure with weak exchange coupling.

    5. Supramolecular Chemistry

      Amidinium Carboxylate Salt Bridges as a Recognition Motif for Mechanically Interlocked Molecules: Synthesis of an Optically Active [2]Catenane and Control of Its Structure (pages 5463–5467)

      Yuji Nakatani, Yoshio Furusho and Eiji Yashima

      Article first published online: 25 JUN 2010 | DOI: 10.1002/anie.201002382

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      Salty catenane: An optically active [2]catenane was synthesized by utilizing an amidinium carboxylate salt bridge (see picture). The relative motion of the two macrocyclic components was completely controlled by an acid/base or Zn2+/cryptand couple.

    6. Main-Group Chemistry

      Monomeric Organoantimony(I) and Organobismuth(I) Compounds Stabilized by an NCN Chelating Ligand: Syntheses and Structures (pages 5468–5471)

      Petr Šimon, Frank de Proft, Roman Jambor, Aleš Růžička and Libor Dostál

      Article first published online: 2 JUL 2010 | DOI: 10.1002/anie.201002209

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      One on one: A combination of steric effects and M[BOND]N interactions of a rigid NCN pincer ligand allows the isolation and characterization of monomeric stibinidene and bismuthinidene compounds. The structure and bonding was confirmed by crystallographic studies (see picture; Sb or Bi yellow, N blue) and calculations.

    7. Nanotechnology

      Side-by-Side and End-to-End Gold Nanorod Assemblies for Environmental Toxin Sensing (pages 5472–5475)

      Libing Wang, Yingyue Zhu, Liguang Xu, Wei Chen, Hua Kuang, Liqiang Liu, Ashish Agarwal, Chuanlai Xu and Nicholas A. Kotov

      Article first published online: 2 JUL 2010 | DOI: 10.1002/anie.200907357

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      Parallel or angle parked: Gold nanorods (see picture) were selectively modified either on the sides or ends using complementary microcystin (MC-LR) antibody and antigen (blue). Fast detection of MC-LR (green) was successfully achieved with these assemblies, and both sensitivity and detection ranges were markedly better for the end-to-end motif (right) than the side-to-side variant (left).

    8. Chemical Imaging

      Label-Free, Real-Time Monitoring of Biomass Processing with Stimulated Raman Scattering Microscopy (pages 5476–5479)

      Brian G. Saar, Yining Zeng, Christian W. Freudiger, Yu-San Liu, Michael E. Himmel, X. Sunney Xie and Shi-You Ding

      Article first published online: 29 JUN 2010 | DOI: 10.1002/anie.201000900

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      Label-free “chemical movies” of lignin and cellulose in fresh plant tissue were recorded during a step in the breakdown of biomass to produce biofuels by using stimulated Raman scattering microscopy. The technique allows the degradation of lignin in the cell wall to be monitored with high sensitivity, sub-micrometer spatial resolution, and high temporal resolution.

    9. Rational Catalyst Design

      Phosphorus Ligand Imaging with Two-Photon Fluorescence Spectroscopy: Towards Rational Catalyst Immobilization (pages 5480–5484)

      Fabrizio Marras, Alexander M. Kluwer, Joanna R. Siekierzycka, Alessandro Vozza, Albert M. Brouwer and Joost N. H. Reek

      Article first published online: 2 JUL 2010 | DOI: 10.1002/anie.201000907

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      Spotless catalysts: Ligand immobilization was studied by two-photon fluorescence microscopy with a fluorescent nixantphos ligand as probe (see picture). In the immobilization process ligand aggregates form in solution and are deposited on the support, where they appear as bright spots in fluorescence images. Preventing their formation leads to “spotless” catalysts with superior catalytic properties.

    10. Charged Phosphiranes

      Synthesis, Structure, and Reactivity of a Stabilized Phosphiranylium Salt (pages 5485–5488)

      Helen Jansen, Florian B. Läng, J. Chris Slootweg, Andreas W. Ehlers, Martin Lutz, Koop Lammertsma and Hansjörg Grützmacher

      Article first published online: 2 JUL 2010 | DOI: 10.1002/anie.201000901

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      Charged! Combining MeBABAR-Phos and methyl triflate affords an amino-stabilized phosphiranylium ion (see picture; C gray, N blue, P orange), which undergoes various nucleophilic addition reactions to give P-substituted phosphiranes and an N-heterocyclic carbene stabilized phosphiranylium cation.

    11. Protein Folding

      Design and Folding of [GluA4(OβThrB30)]Insulin (“Ester Insulin”): A Minimal Proinsulin Surrogate that Can Be Chemically Converted into Human Insulin (pages 5489–5493)

      Youhei Sohma, Qing-Xin Hua, Jonathan Whittaker, Michael A. Weiss and Stephen B. H. Kent

      Article first published online: 27 MAY 2010 | DOI: 10.1002/anie.201001151

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      Insulin folding: An ester-linked polypeptide proinsulin surrogate folded efficiently with concomitant disulfide bond formation, and saponification gave native insulin having full biological activity. This strategy overcomes the low yield combination of individual insulin A and B chains, and provides a simple and effective approach to the total chemical synthesis of human insulin and its analogues.

    12. Carbohydrate Detection

      Assessment of Tumor Metastasis by the Direct Determination of Cell-Membrane Sialic Acid Expression (pages 5494–5497)

      Akira Matsumoto, Horacio Cabral, Naoko Sato, Kazunori Kataoka and Yuji Miyahara

      Article first published online: 23 JUN 2010 | DOI: 10.1002/anie.201001220

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      In a world without labels… A self-assembled phenylboronic acid monolayer on the surface of a gold electrode enabled the potentiometric detection of cell-membrane sialic acid (SA; see diagram) and differentiation of healthy pneumocytes from metastatic melanoma cells on the basis of altered SA expression. This approach to the diagnosis of tumoral malignancy or the degree of metastasis holds promise for label-free, noninvasive, real-time cytology.

    13. Biomolecule Detection

      Ultrasensitive Detection of microRNAs by Exponential Isothermal Amplification (pages 5498–5501)

      Hongxia Jia, Zhengping Li, Chenghui Liu and Yongqiang Cheng

      Article first published online: 2 JUL 2010 | DOI: 10.1002/anie.201001375

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      Tiny amounts of a given miRNA (0.1 zmol) can be detected accurately and quantitatively by a real-time method based on an exponential amplification reaction (see picture). The proposed method has a wide dynamic range of more than 10 orders of magnitude, can be carried out within 30 minutes under isothermal conditions, and requires no modified DNA probes. It clearly discriminates miRNA sequences that differ by one base.

    14. Coherent Quenching

      Coherent Quenching of a Fluorophore for the Design of a Highly Sensitive In-Stem Molecular Beacon (pages 5502–5506)

      Yuichi Hara, Taiga Fujii, Hiromu Kashida, Koji Sekiguchi, Xingguo Liang, Kosuke Niwa, Tomokazu Takase, Yasuko Yoshida and Hiroyuki Asanuma

      Article first published online: 2 JUL 2010 | DOI: 10.1002/anie.201001459

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      Excitonic interaction was utilized to design a highly sensitive in-stem molecular beacon (ISMB) in which both a fluorophore and a quencher on D-threoninols are incorporated as a pseudo base pair (see scheme; optimized combination with Cy3 and modified Methyl Red). Minimization of the difference between λmax of the fluorophore and quencher maximized quenching efficiency.

    15. Photoisomerization

      The Catalytic Z to E Isomerization of Stilbenes in a Photosensitizing Porous Coordination Network (pages 5507–5509)

      Kazuaki Ohara, Yasuhide Inokuma and Makoto Fujita

      Article first published online: 28 JUN 2010 | DOI: 10.1002/anie.201001902

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      One way only: The Z[RIGHTWARDS ARROW]E photoisomerization of stilbene under visible light occurs within a porous coordination network (see picture). The reaction proceeds through the photoexcitation of a charge-transfer complex between the highly electron-deficient ligand and the stilbene in the pore. The in situ formed E isomer rapidly exchanges with unreacted Z isomer in solution, hence a catalytic amount of the network is sufficient to promote the reaction.

    16. Biorefinery

      Selective and Flexible Transformation of Biomass-Derived Platform Chemicals by a Multifunctional Catalytic System (pages 5510–5514)

      Frank M. A. Geilen, Barthel Engendahl, Andreas Harwardt, Wolfgang Marquardt, Jürgen Klankermayer and Walter Leitner

      Article first published online: 28 JUN 2010 | DOI: 10.1002/anie.201002060

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      A sustainable supply chain: The controlled transformation of the biomass-derived platform compounds levulinic acid (LA) and itaconic acid (IA) into the corresponding lactones, diols, or cyclic ethers (see picture) by using a multifunctional molecular catalyst is described.

    17. Nanostructures

      Combining Metallasupramolecular Chemistry with Dynamic Covalent Chemistry: Synthesis of Large Molecular Cages (pages 5515–5518)

      Anton Granzhan, Thomas Riis-Johannessen, Rosario Scopelliti and Kay Severin

      Article first published online: 6 JUL 2010 | DOI: 10.1002/anie.201002748

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      Ru-built cube: By combining metallasupramolecular chemistry with dynamic covalent chemistry, complex nanostructures can be formed. Large cages are synthesized by reaction of trinuclear metallamacrocycles containing pendant aldehyde groups (see picture; Ru blue, aldehyde linkers green) with triamines (red).

    18. Gold Catalysis

      Gold-Catalyzed Intramolecular Aminoarylation of Alkenes: C[BOND]C Bond Formation through Bimolecular Reductive Elimination (pages 5519–5522)

      William E. Brenzovich Jr., Diego Benitez, Aaron D. Lackner, Hunter P. Shunatona, Ekaterina Tkatchouk, William A. Goddard III and F. Dean Toste

      Article first published online: 2 JUL 2010 | DOI: 10.1002/anie.201002739

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      Gold-ilocks and the 3 mol % catalyst: Bimetallic gold bromides allow the room temperature aminoarylation of unactivated terminal olefins with aryl boronic acids using Selectfluor as an oxidant. A catalytic cycle involving gold(I)/gold(III) and a bimolecular reductive elimination for the key C[BOND]C bond-forming step is proposed. dppm= bis(diphenylphosphanyl)methane.

    19. Fused-Ring Systems

      Fused Pyrene–Diporphyrins: Shifting Near-Infrared Absorption to 1.5 μm and Beyond (pages 5523–5526)

      Vyacheslav V. Diev, Kenneth Hanson, Jeramy D. Zimmerman, Stephen R. Forrest and Mark E. Thompson

      Article first published online: 2 JUL 2010 | DOI: 10.1002/anie.201002669

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      Sticking together: Direct fusion of pyrene rings with diporphyrins can be achieved without prior activation of aromatic rings. This simple method gives pyrene–diporphyrin hybrids (see picture, C (pyrene) red, C (porphyrin) dark blue, N light blue, Zn green) with a high near-infrared (NIR) absorption that reaches the wavelengths required for use in telecommunications.

    20. Total Synthesis

      Stereoselective Total Synthsis of (±)-Urechitol A (pages 5527–5528)

      Tatsunobu Sumiya, Ken Ishigami and Hidenori Watanabe

      Article first published online: 2 JUL 2010 | DOI: 10.1002/anie.201002505

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      I want to ride my tricycle: Urechitol A was synthesized as a racemate by using a [4+3] cycloaddition reaction and methanol assisted intramolecular epoxide opening as the key steps for the efficient construction of the core tricyclic framework. The overall yield was 2.3 % over 12 steps. Bn=benzyl, TES=triethylsilyl.

    21. Oxidative Amination

      Modular Synthesis of 1,2-Diamine Derivatives by Palladium-Catalyzed Aerobic Oxidative Cyclization of Allylic Sulfamides (pages 5529–5532)

      Richard I. McDonald and Shannon S. Stahl

      Article first published online: 25 JUN 2010 | DOI: 10.1002/anie.200906342

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      Allylic sulfamides undergo aerobic oxidative cyclization at room temperature, mediated by a Pd(O2CCF3)2/DMSO catalyst system in tetrahydrofuran. The cyclic sulfamide products are readily converted into 1,2-diamines, and substrates derived from chiral allylic amines cyclize with very high diastereoselectivity.

    22. Homogeneous Catalysis

      Probing the Mechanism of Olefin Metathesis in Grubbs–Hoveyda and Grela Type Complexes (pages 5533–5536)

      Tim Vorfalt, Klaus-Jürgen Wannowius and Herbert Plenio

      Article first published online: 2 JUL 2010 | DOI: 10.1002/anie.201000581

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      The more the better: Kinetic data derived from UV/Vis spectroscopy (see picture) provide conclusive evidence for participation of the olefinic substrate in the rate-limiting step of the initiation reaction of Grubbs–Hoveyda type olefin metathesis catalysts, and for a second olefin-independent step, which is rate-limiting only at very high olefin concentrations.

    23. Electrets

      Selective Discharge of Electrostatic Charges on Electrets Using a Patterned Hydrogel Stamp (pages 5537–5540)

      Xinlei Ma, Dan Zhao, Mianqi Xue, Hai Wang and Tingbing Cao

      Article first published online: 2 JUL 2010 | DOI: 10.1002/anie.201000766

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      Paint with water: A topographically patterned agarose hydrogel stamp transfers and prints water onto uniformly charged PMMA electrets for selectively discharging electrostatic charges. The high-resolution electrostatic charge patterns produced by this simple approach can induce the reduction of metal ions and allow the fabrication of micro- and nanoscale metallic arrays.

    24. Polyarylated Methanes

      Synthesis of Polyarylated Methanes through Cross-Coupling of Tricarbonylchromium-Activated Benzyllithiums (pages 5541–5544)

      Genette I. McGrew, Jesada Temaismithi, Patrick J. Carroll and Patrick J. Walsh

      Article first published online: 2 JUL 2010 | DOI: 10.1002/anie.201000957

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      Support group: Coordinated to the tricarbonylchromium fragment, a typically unstable benzylic organolithium can participate directly in cross-coupling reactions with aryl bromides to form polyarylated methane derivatives (see scheme). Cr(CO)3 assistance leads to reactivity with a variety of coordinated substrates and—given multiple benzylic sites—can effect up to six coupling events per arene.

    25. Heterogeneous Catalysis

      Supported Gold and Silver Nanoparticles for Catalytic Deoxygenation of Epoxides into Alkenes (pages 5545–5548)

      Takato Mitsudome, Akifumi Noujima, Yusuke Mikami, Tomoo Mizugaki, Koichiro Jitsukawa and Kiyotomi Kaneda

      Article first published online: 12 MAY 2010 | DOI: 10.1002/anie.201001055

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      Taking the ′O′: Supported gold and silver nanoparticles (NPs), which are well-known epoxidation catalysts, were found to have intrinsic catalytic ability for the deoxygenation of epoxides into alkenes using alcohol as a reductant (see picture). The selectivity for all the alkenes were over 99 %, and an excellent turnover number was achieved. Furthermore, these supported gold and silver nanoparticles were recyclable.

    26. Nanoparticle Catalysis

      Hydrodeoxygenation of Lignin-Derived Phenols into Alkanes by Using Nanoparticle Catalysts Combined with Brønsted Acidic Ionic Liquids (pages 5549–5553)

      Ning Yan, Yuan Yuan, Ryan Dykeman, Yuan Kou and Paul J. Dyson

      Article first published online: 30 JUN 2010 | DOI: 10.1002/anie.201001531

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      Oxy-gone in a tandem: A catalytic system composed of metal nanoparticles (NPs) and a functionalized Brønsted acidic ionic liquid (IL), both of which are immobilized in a nonfunctionalized IL, is highly efficient in upgrading lignin-derived phenolic compounds into alkanes; the hydrogenation and dehydration reactions take place in tandem.

    27. Synthetic Biology

      Artificial Genetic Systems: Self-Avoiding DNA in PCR and Multiplexed PCR (pages 5554–5557)

      Shuichi Hoshika, Fei Chen, Nicole A. Leal and Steven A. Benner

      Article first published online: 28 JUN 2010 | DOI: 10.1002/anie.201001977

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      Discerning in their choice of partner: The DNA of a self-avoiding molecular-recognition system (SAMRS) binds to natural DNA but not to members of the same SAMRS. Multiplexed PCR with an SAMRS based on 2-aminopurine (A*), 2-thiothymine (T*), 2′-hypoxanthine (G*), and N4-ethylcytosine (C*; see examples) showed the benefits of such systems for clinical analysis, which requires many DNA molecules to interact with target DNA but not with each other.

    28. C[BOND]H Activation

      Enantioselective Oxidative Cross-Coupling Reaction of 3-Indolylmethyl C[BOND]H Bonds with 1,3-Dicarbonyls Using a Chiral Lewis Acid-Bonded Nucleophile to Control Stereochemistry (pages 5558–5562)

      Chang Guo, Jin Song, Shi-Wei Luo and Liu-Zhu Gong

      Article first published online: 29 JUN 2010 | DOI: 10.1002/anie.201002108

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      A highly enantioselective C[BOND]H-activation-based oxidative coupling reaction of 3-arylmethylindole derivatives with dibenzyl malonate by using chiral Lewis acid bonded nucleophiles provided an approach to indole derivatives (see scheme; DDQ=2,3-dichloro-5,6-dicyano-1,4-benzoquinone, OTf=trifluoromethanesulfonate).

    29. Arynes

      Preparation and Regioselective Diels–Alder Reactions of Borylbenzynes: Synthesis of Functionalized Arylboronates (pages 5563–5566)

      Takashi Ikawa, Akira Takagi, Yurio Kurita, Kozumo Saito, Kenji Azechi, Masahiro Egi, Keisuke Kakiguchi, Yasuyuki Kita and Shuji Akai

      Article first published online: 2 JUL 2010 | DOI: 10.1002/anie.201002191

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      B+[4+2]: 3-Borylbenzynes undergo Diels–Alder reactions with substituted furans and pyrroles to give highly functionalized arylboronic acid derivatives with either good or exclusive regioselectivities (see picture). The effect of the boryl group on the regioselectivity arises from electronic rather than steric effects.

    30. Nucleophilic Catalysis

      Chiral Ammonium Betaines as Ionic Nucleophilic Catalysts (pages 5567–5569)

      Daisuke Uraguchi, Kyohei Koshimoto, Shuhei Miyake and Takashi Ooi

      Article first published online: 7 JUL 2010 | DOI: 10.1002/anie.201002315

      Thumbnail image of graphical abstract

      Catalyst debut: The chiral ammonium betaine 1 has been successfully applied to the asymmetric Steglich rearrangement as an ionic nucleophilic catalyst. The catalyzed reaction results in record levels of product enantioselectivity, and has a broad substrate scope. M.S.=molecular sieves, Troc=2,2,2-trichloroethoxycarbonyl.

    31. Planar Four-Coordinate Carbon

      A Monomeric Dilithio Methandiide with a Distorted trans-Planar Four-Coordinate Carbon (pages 5570–5573)

      Oliver J. Cooper, Ashley J. Wooles, Jonathan McMaster, William Lewis, Alexander J. Blake and Stephen T. Liddle

      Article first published online: 29 JUN 2010 | DOI: 10.1002/anie.201002483

      Thumbnail image of graphical abstract

      It's plain to see: A monomeric dilithio methandiide features a distorted trans-planar four-coordinate carbon atom. The nature of this compound as established by an X-ray diffraction study (see picture: C black, N blue, P magenta, Li red) and supported by calculations.

    32. Natural Product Synthesis

      Total Synthesis and Structural Reassignment of (+)-Dictyosphaeric Acid A: A Tandem Intramolecular Michael Addition/Alkene Migration Approach (pages 5574–5577)

      Alan R. Burns, Graeme D. McAllister, Stephen E. Shanahan and Richard J. K. Taylor

      Article first published online: 25 JUN 2010 | DOI: 10.1002/anie.201002416

      Thumbnail image of graphical abstract

      The acid test? The synthetic route to the title compound features a Z-selective ring-closing metathesis reaction and an E-selective tandem intramolecular Michael addition/alkene migration sequence as the key transformations. The stereochemical configuration of the product was reassigned based on NMR studies.

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      Preview: Angew. Chem. Int. Ed. 33/2010 (page 5581)

      Article first published online: 22 JUL 2010 | DOI: 10.1002/anie.201090101

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