Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 29

July 16, 2012

Volume 51, Issue 29

Pages 7051–7332

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Obituary
    8. Book Reviews
    9. Highlights
    10. Essay
    11. Minireviews
    12. Review
    13. Communications
    14. Preview
    1. Cover Picture: Sialyl Lewisx: A “Pre-Organized Water Oligomer”? (Angew. Chem. Int. Ed. 29/2012) (page 7051)

      Dr. Florian P. C. Binder, Dr. Katrin Lemme, Roland C. Preston and Prof. Dr. Beat Ernst

      Article first published online: 2 JUL 2012 | DOI: 10.1002/anie.201204559

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      A surrogate for clustered water molecules attached to a scaffold is how the “pre-organized water oligomer” sialyl Lewisx can be described. The impetus for its binding to E-selectin is investigated by B. Ernst et al. in their Communication on page 7327 ff. Using isothermal titration calorimetry they show the key factors are the high degree of pre-organization allowing an array of directed hydrogen bonds, and the entropic benefit on releasing water molecules from the large binding interface.

    2. Inside Cover: Cmath image[BOND]H Bond Activation Triggered by Formation of Metallacycles: Rhodium(I)-Catalyzed Cyclopropanation/Cyclization of Allenynes (Angew. Chem. Int. Ed. 29/2012) (page 7052)

      Dr. Yoshihiro Oonishi, Yoshitaka Kitano and Prof. Dr. Yoshihiro Sato

      Article first published online: 4 JUL 2012 | DOI: 10.1002/anie.201204860

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      Transition-metal-catalyzed activations of Cmath image[BOND]H bonds usually need the assistance of directing groups for site-selective activation. In their Communication on page 7305 ff., Y. Oonishi, Y. Sato, and co-workers describe a new method for the activation of Cmath image[BOND]H bonds; this activation is triggered by the formation of a metallacycle. In the picture, the statue of Dr. William S. Clark points out the hydrogen that should be activated in the key step of this reaction.

    3. Inside Back Cover: Copper Catalyst Activation Driven by Photoinduced Electron Transfer: A Prototype Photolatent Click Catalyst (Angew. Chem. Int. Ed. 29/2012) (page 7333)

      Lydie Harmand, Sarah Cadet, Dr. Brice Kauffmann, Dr. Luca Scarpantonio, Dr. Pinar Batat, Dr. Gediminas Jonusauskas, Dr. Nathan D. McClenaghan, Dr. Dominique Lastécouères and Dr. Jean-Marc Vincent

      Article first published online: 6 JUL 2012 | DOI: 10.1002/anie.201204564

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      As light changes night (yin) into day (yang), irradiation of the click-inactive copper(II) tren ketoprofenate complex triggers an efficient photoinduced electron-transfer process to provide a highly active copper(I) tren click catalyst. In their Communication on page 7137 ff., J.-M. Vincent et al. also show that by simply introducing air into the reaction medium the catalysis can be switched off, and then on again by bubbling argon followed by irradiation.

    4. Back Cover: Rhodium(III)-Catalyzed C[BOND]H Activation of Arenes Using a Versatile and Removable Triazene Directing Group (Angew. Chem. Int. Ed. 29/2012) (page 7334)

      Chengming Wang, Hu Chen, Zhaofeng Wang, Jiean Chen and Prof. Dr. Yong Huang

      Article first published online: 26 JUN 2012 | DOI: 10.1002/anie.201204565

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      C[BOND]H activation/functionalization is one of the most effective ways to assemble complex organic scaffolds. A vital limitation is the need for a directing group that remains in the product architecture and restricts structural diversity. In their Communication on page 7242 ff., Y. Huang et al. describe a triazine directing group for Cmath image[BOND]H activation/functionalization. This group exhibits substantial post-functionalization synthetic versatility, thus allowing for a range of further transformations.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Obituary
    8. Book Reviews
    9. Highlights
    10. Essay
    11. Minireviews
    12. Review
    13. Communications
    14. Preview
  3. Corrigendum

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Obituary
    8. Book Reviews
    9. Highlights
    10. Essay
    11. Minireviews
    12. Review
    13. Communications
    14. Preview
    1. You have free access to this content
      Corrigendum: Highly Luminescent Nanocrystals From Removal of Impurity Atoms Residual From Ion-Exchange Synthesis (page 7069)

      Dr. Prashant K. Jain, Brandon J. Beberwyck, Lam-Kiu Fong, Dr. Mark J. Polking and Prof. A. Paul Alivisatos

      Article first published online: 11 JUL 2012 | DOI: 10.1002/anie.201204566

      This article corrects:

      Highly Luminescent Nanocrystals From Removal of Impurity Atoms Residual From Ion-Exchange Synthesis1

      Vol. 51, Issue 10, 2387–2390, Article first published online: 25 JAN 2012

  4. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Obituary
    8. Book Reviews
    9. Highlights
    10. Essay
    11. Minireviews
    12. Review
    13. Communications
    14. Preview
  5. Author Profile

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Obituary
    8. Book Reviews
    9. Highlights
    10. Essay
    11. Minireviews
    12. Review
    13. Communications
    14. Preview
    1. Barry M. Trost (pages 7074–7076)

      Article first published online: 12 MAR 2012 | DOI: 10.1002/anie.201201017

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      “What I first look for in a publication is to learn something I did not know. The most important thing I learned from my parents is self-reliance. …” This and more about Barry M. Trost can be found on page 7074.

  6. Obituary

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Obituary
    8. Book Reviews
    9. Highlights
    10. Essay
    11. Minireviews
    12. Review
    13. Communications
    14. Preview
  7. Book Reviews

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Obituary
    8. Book Reviews
    9. Highlights
    10. Essay
    11. Minireviews
    12. Review
    13. Communications
    14. Preview
    1. Molecular Cluster Magnets. Edited by Richard Winpenny. (pages 7079–7080)

      Rodolphe Clérac

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201202869

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      World Scientific Books, Singapore 2011. 312 pp., hardcover, $ 95.00.—ISBN 978-9814322942

    2. Kinetics of Chemical Reactions. Decoding Complexity. By Guy Marin and Gregory S. Yablonsky. (pages 7080–7081)

      Frerich J. Keil

      Article first published online: 22 JUN 2012 | DOI: 10.1002/anie.201203510

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      Wiley-VCH, Weinheim, 2011. 428 pp., hardcover, € 79.00.—ISBN 978-3527317639

  8. Highlights

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Obituary
    8. Book Reviews
    9. Highlights
    10. Essay
    11. Minireviews
    12. Review
    13. Communications
    14. Preview
    1. Geodesic Polynuclear Arene

      Synthesis of Geodesic Polynuclear Arenes and Fullerenes by Intramolecular Aryl–Aryl Coupling (pages 7082–7084)

      Prof. Carlo Thilgen

      Article first published online: 6 JUL 2012 | DOI: 10.1002/anie.201204181

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      Bending over backwards to build buckybowls and -balls? For the last two decades, flash vacuum pyrolysis of chloro- and bromoarenes has been the method of choice for intramolecular aryl–aryl couplings that afford geodesic polynuclear arenes (“buckybowls”) including fullerene C60. Recently, even fluoroarenes were subjected under relatively mild conditions to intramolecular CAr[BOND]CAr couplings by combining the cleavage of CAr[BOND]F with the formation of very strong Si[BOND]F or Al[BOND]F bonds (see picture; green C, white H).

    2. Cyclopropanes

      One Pot, Two Phases: Iron-Catalyzed Cyclopropanation with In Situ Generated Diazomethane (pages 7085–7086)

      Dipl.-Chem. Johannes Kaschel, Dipl.-Chem. Tobias F. Schneider and Dr. Daniel B. Werz

      Article first published online: 14 JUN 2012 | DOI: 10.1002/anie.201203829

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      Tamed! The safe handling of diazomethane can be accomplished by a two-phase reaction. After being generated in aqueous media, the highly reactive species transfers to the organic phase and directly converts alkenes into cyclopropanes (see scheme). An air-stable iron(III) porphyrin complex serves as the catalyst.

  9. Essay

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Obituary
    8. Book Reviews
    9. Highlights
    10. Essay
    11. Minireviews
    12. Review
    13. Communications
    14. Preview
    1. Philosophy of Science

      Modern Science: A Case of Collective Intelligence? On the Role of Thought Economy and Gratifying Attention in Knowledge Production (pages 7088–7092)

      Prof. Dr. Georg Franck

      Article first published online: 15 JUN 2012 | DOI: 10.1002/anie.201201013

      Your attention please: Phenomenal conciousness, that is, how something feels, does not exist for an observer. As science relies on observations, it is not aware of the nature of subjectivity and thus science is not often defined as a collective intelligence. In this Essay, the roles of intelligence and attention are discussed, as well as an analysis of scientific communication and citation, in order to evaluate whether science is a case of collective intelligence.

  10. Minireviews

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Obituary
    8. Book Reviews
    9. Highlights
    10. Essay
    11. Minireviews
    12. Review
    13. Communications
    14. Preview
    1. Carbon Nanotubes

      para-Connected Cyclophenylenes and Hemispherical Polyarenes: Building Blocks for Single-Walled Carbon Nanotubes? (pages 7094–7101)

      Prof. Uwe H. F. Bunz, Dipl.-Chem. Sebastian Menning and Prof. Nazario Martín

      Article first published online: 30 APR 2012 | DOI: 10.1002/anie.201201494

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      Carbon nanotubes by design? Cyclo-para-phenylenes are monomers for the synthesis of armchair carbon nanotubes (see picture, right), and are also attractive fluorophores that display size-dependent emission properties. Geodesic polyarenes represent a realistic alternative for the rational design of carbon nanotubes through the chemical elongation of the hydrocarbon template (left).

    2. Smart Materials

      Functional Organic Materials Based on Polymerized Liquid-Crystal Monomers: Supramolecular Hydrogen-Bonded Systems (pages 7102–7109)

      Prof. Dr. Dirk J. Broer, Prof. Dr. Cees M. W. Bastiaansen, Dr. Michael G. Debije and Dr. Albertus P. H. J. Schenning

      Article first published online: 15 MAY 2012 | DOI: 10.1002/anie.201200883

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      Get smart: The self-assembly of liquid crystals can be used to prepare well-defined nanostructured functional materials. The picture shows a polymer film composed of hydrogen-bonded dimers and a cross-linker that curls and straightens in response to changes in the relative humidity.

  11. Review

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Obituary
    8. Book Reviews
    9. Highlights
    10. Essay
    11. Minireviews
    12. Review
    13. Communications
    14. Preview
    1. Biochemistry

      Structure and Function of Noncanonical Nucleobases (pages 7110–7131)

      Prof. Dr. Thomas Carell, MChem. Caterina Brandmayr, Dipl.-Chem. Antje Hienzsch, Dr. Markus Müller, Dr. David Pearson, Dipl.-Chem. Veronika Reiter, M. Sc. Ines Thoma, M. Sc. Peter Thumbs and Dipl.-Chem. Mirko Wagner

      Article first published online: 28 JUN 2012 | DOI: 10.1002/anie.201201193

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      Besides their four canonical nucleobases, DNA and RNA contain a variety of highly modified nucleosides including the epigenetic bases mC, hmC, fC, and caC (see scheme), which are able to increase the chemical information content. The function of these modified bases is to generate a second level of chemical complexity in RNA and DNA in addition to the first coding level provided by the sequence of the canonical Watson–Crick bases.

  12. Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Obituary
    8. Book Reviews
    9. Highlights
    10. Essay
    11. Minireviews
    12. Review
    13. Communications
    14. Preview
    1. Enzyme Catalysis

      Bio-Click Chemistry: Enzymatic Functionalization of PEGylated Capsules for Targeting Applications (pages 7132–7136)

      Melissa K. M. Leung, Dr. Christoph E. Hagemeyer, Dr. Angus P. R. Johnston, Catalina Gonzales, Marloes M. J. Kamphuis, Katie Ardipradja, Dr. Georgina K. Such, Prof. Karlheinz Peter and Prof. Frank Caruso

      Article first published online: 28 JUN 2012 | DOI: 10.1002/anie.201203612

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      All sorted: The enzyme Sortase A was used to catalyze functionalization of PEGylated capsules with an activation-specific anti-platelet single-chain antibody (scFv). This enzymatic method allows fast, covalent, and site-directed functionalization of delivery vehicles under mild conditions. Activation-specific anti-platelet scFv-coated PEGylated capsules exhibited a high level of selective binding to thrombi, thus suggesting their potential for thrombosis therapy.

    2. Switchable Catalyst

      Copper Catalyst Activation Driven by Photoinduced Electron Transfer: A Prototype Photolatent Click Catalyst (pages 7137–7141)

      Lydie Harmand, Sarah Cadet, Dr. Brice Kauffmann, Dr. Luca Scarpantonio, Dr. Pinar Batat, Dr. Gediminas Jonusauskas, Dr. Nathan D. McClenaghan, Dr. Dominique Lastécouères and Dr. Jean-Marc Vincent

      Article first published online: 6 JUL 2012 | DOI: 10.1002/anie.201203014

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      PET cat. While the copper(II) tren ketoprofenate precatalyst 1 (see picture) is inactive at room temperature in methanol, it is quantitatively and rapidly reduced to its cuprous state upon light irradiation to provide a highly reactive click catalyst. By simply introducing air into the reaction medium the catalysis can be switched off and then switched on again by bubbling argon followed by irradiation.

    3. Nanostructures

      Setting the Environmental Conditions for Controlling Gold Nanoparticle Assemblies (pages 7142–7145)

      Meital Orbach, Dr. Michal Lahav, Dr. Petr Milko, Dr. Sharon G. Wolf and Prof. Milko E. van der Boom

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201203291

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      Fundamental insights into the factors that control the properties and structure of gold nanoparticle (AuNP) based assemblies enable the design and construction of new materials. The dimensions (shape and size) and the optical properties of AuNP assemblies are affected by the electronic properties of the organic cross-linker and the nature of the AuNPs.

    4. Responsive Gels

      Local Switching of Chemical Patterns through Light-Triggered Unfolding of Creased Hydrogel Surfaces (pages 7146–7149)

      Jinhwan Yoon, Pei Bian, Jungwook Kim, Thomas J. McCarthy and Ryan C. Hayward

      Article first published online: 12 JUN 2012 | DOI: 10.1002/anie.201202692

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      Visible light induces switching of surface chemical patterns based on hybrid gels of thermally responsive poly(N-isopropyl acrylamide) copolymer networks containing iron oxide nanoparticles. The swelling of these hybrid gels is reduced upon illumination (see picture), allowing controlled unfolding of creased features formed owing to an elastic surface instability.

    5. Membrane Proteins

      A Highly Charged Voltage-Sensor Helix Spontaneously Translocates across Membranes (pages 7150–7153)

      Dr. Jing He, Dr. Kalina Hristova and Dr. William C. Wimley

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201202741

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      Moving freely: A recent model for voltage gating of potassium channels proposed that the four arginine residues of the voltage-sensing S4 helix (left) are in direct contact with the membrane lipids and move into the hydrocarbon core of the membrane during gating. It is demonstrated that the physical properties of the isolated S4 sequence (right) are sufficient to allow it to freely translocate across synthetic membranes.

    6. Organic Cages

      Porous Organic Alloys (pages 7154–7157)

      Dr. Tom Hasell, Dr. Samantha Y. Chong, Dr. Marc Schmidtmann, Dr. Dave J. Adams and Prof. Andrew I. Cooper

      Article first published online: 8 JUN 2012 | DOI: 10.1002/anie.201202849

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      Another brick in the wall: Porous ternary cocrystals were prepared by chiral recognition between organic cage modules. One module, CC1, is ordered on 50 % of the lattice positions with respect to two other modules, CC3 and CC4, that are disordered across the other 50 % of sites (see picture). There is a linear relationship between relative module composition and the cocrystal lattice parameters.

    7. Silicon Chemistry

      Synthesis and Characterization of an Isolable Base-Stabilized Silacycloprop-1-ylidene (pages 7158–7161)

      Dr. Ricardo Rodriguez, Thibault Troadec, Dr. Tsuyoshi Kato, Dr. Nathalie Saffon-Merceron, Dr. Jean-Marc Sotiropoulos and Dr. Antoine Baceiredo

      Article first published online: 27 APR 2012 | DOI: 10.1002/anie.201201581

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      Strained but stable: An isolable silacycloprop-1-ylidene stabilized by intramolecular complexation with an iminophosphorus ylide fragment was successfully synthesized and fully characterized. The formation of this small highly strained cyclic silylene involves an unprecedented SiIV[RIGHTWARDS ARROW]SiII rearrangement under very mild conditions.

    8. High-Temperature Superconductors

      Tuning the Critical Temperature of Cuprate Superconductor Films with Self-Assembled Organic Layers (pages 7162–7165)

      Dr. Itai Carmeli, Avraham Lewin, Erez Flekser, Itay Diamant, Qiang Zhang, Prof. Jingshan Shen, Dr. Michael Gozin, Dr. Shachar Richter and Prof. Yoram Dagan

      Article first published online: 12 APR 2012 | DOI: 10.1002/anie.201201606

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      Control over the Tc value of high-Tc superconductors by self-assembled monolayers is demonstrated (Tc=critical temperature). Molecular control was achieved by adsorption of polar molecules on the superconductor surface (see scheme) that change its carrier concentration through charge transport or light-induced polarization.

    9. Dynamic Membranes

      Dynamic Interactive Membranes with Pressure-Driven Tunable Porosity and Self-Healing Ability (pages 7166–7170)

      Prashant Tyagi, Dr. André Deratani, Dr. Denis Bouyer, Didier Cot, Valérie Gence, Dr. Mihail Barboiu, Dr. Trang N. T. Phan, Prof. Denis Bertin, Dr. Didier Gigmes and Dr. Damien Quemener

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201201686

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      When pressure is applied to dynamic interactive membranes consisting of micelles composed of a triblock copolymer, their morphologies can be fine-tuned. Membranes with a range of porosities are accessible which can regulate and thereby control filtration performance and also display effective autonomous healing.

    10. Graphite Nanoneedles

      Edge-Plane-Rich Nitrogen-Doped Carbon Nanoneedles and Efficient Metal-Free Electrocatalysts (pages 7171–7175)

      Rafael Silva, Dr. Jafar Al-Sharab and Prof. Dr. Tewodros Asefa

      Article first published online: 8 JUN 2012 | DOI: 10.1002/anie.201201742

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      CNN news: N-doped carbon nanoneedles (CNNs) are synthesized by self-assembling core–shell nanostructures and nanoreactors around cellulose nanoneedles, and subsequent graphitization. The resulting graphitic nanoneedles (see picture) have well-organized graphitic multi-layers and large proportions of N-doped edge planes. The materials serve as efficient metal-free electrocatalysts for hydrazine oxidation.

    11. Fluorescence Imaging

      DNA Polyfluorophores for Real-Time Multicolor Tracking of Dynamic Biological Systems (pages 7176–7180)

      Dr. Shenliang Wang, Dr. Jia Guo, Dr. Toshikazu Ono and Prof. Dr. Eric T. Kool

      Article first published online: 8 JUN 2012 | DOI: 10.1002/anie.201201928

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      Dye-ing to live: Spectral limitations of common organic dyes make it difficult or impossible to visualize and follow multiple biological components in rapidly moving systems. The development of a multispectral set of improved DNA-scaffolded fluorophores is described. Their use in multicolor cellular imaging (see scheme) and in tracking of biological motions on the subsecond timescale is demonstrated.

    12. Biosynthetic Engineering

      Introduction of a Non-Natural Amino Acid into a Nonribosomal Peptide Antibiotic by Modification of Adenylation Domain Specificity (pages 7181–7184)

      Dr. Jenny Thirlway, Dr. Richard Lewis, Laura Nunns, Dr. Majid Al Nakeeb, Matthew Styles, Dr. Anna-Winona Struck, Prof. Colin P. Smith and Prof. Jason Micklefield

      Article first published online: 18 JUN 2012 | DOI: 10.1002/anie.201202043

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      Calcium-dependent antibiotics (CDA) are cyclic lipopeptides assembled by nonribosomal peptide synthetase (NRPS) enzymes. Active site modification of the 3-methyl glutamate activating adenylation (A) domain of the CDA NRPS enables the incorporation of synthetic 3-methyl glutamine into CDA. This provides the first example of how A-domains can be engineered to introduce synthetic “non-natural” amino acids into nonribosomal peptides.

    13. Bioimaging

      Carbon-Dot-Based Dual-Emission Nanohybrid Produces a Ratiometric Fluorescent Sensor for In Vivo Imaging of Cellular Copper Ions (pages 7185–7189)

      Anwei Zhu, Qiang Qu, Xiangling Shao, Biao Kong and Prof. Dr. Yang Tian

      Article first published online: 8 MAR 2012 | DOI: 10.1002/anie.201109089

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      A sensitive biosensor: A strategy for the intracellular imaging of Cu2+ ions has been developed by integrating a recognition molecule, N-(2-aminoethyl)-N,N,N′tris(pyridin-2-ylmethyl)ethane-1,2-diamine (AE-TPEA), into a hybrid system composed of carbon and CdSe/ZnS quantum dots.

    14. Fischer–Tropsch Synthesis

      Suppression of Carbon Deposition in the Iron-Catalyzed Production of Lower Olefins from Synthesis Gas (pages 7190–7193)

      Dr. Ard C. J. Koeken, Hirsa M. Torres Galvis, Dr. Thomas Davidian, Dr. Matthijs Ruitenbeek and Prof. Dr. Krijn P. de Jong

      Article first published online: 12 JUN 2012 | DOI: 10.1002/anie.201200280

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      Pressure leverage: A tapered-element oscillating microbalance was used to evaluate carbon deposition on a highly selective and active supported iron catalyst for the production of lower olefins. With increasing pressure, the H2/CO ratio had a profound effect on the carbon deposition rate and accordingly, conditions leading to minimal carbon deposition, low methane selectivity, and high olefin selectivity were identified.

    15. Polyoxometalates

      Aiding the Self-Assembly of Supramolecular Polyoxometalates under Hydrothermal Conditions To Give Precursors of Complex Functional Oxides (pages 7194–7197)

      Dr. Maricruz Sanchez Sanchez, Dr. Frank Girgsdies, Mateusz Jastak, Pierre Kube, Prof. Dr. Robert Schlögl and Dr. Annette Trunschke

      Article first published online: 8 JUN 2012 | DOI: 10.1002/anie.201200746

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      In situ Raman spectroscopy allows insight into molecular processes under hydrothermal conditions during synthesis of complex nanostructured MoVTeNb oxides (see picture: Nb yellow, Mo blue, V/Mo pale blue, Te red). Based on the knowledge acquired, the synthesis can be more efficiently directed towards the desired product with improved functionality.

    16. DNA Recognition and Scission

      G-Rich Sequence-Specific Recognition and Scission of Human Genome by PNA/DNA Hybrid G-Quadruplex Formation (pages 7198–7202)

      Dr. Takumi Ishizuka, Jie Yang, Prof. Dr. Makoto Komiyama and Prof. Dr. Yan Xu

      Article first published online: 14 JUN 2012 | DOI: 10.1002/anie.201201176

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      Hole in one: A single peptide nucleic acid (PNA) effectively targets the G-rich region in double-stranded DNA through formation of a PNA/DNA hybrid G-quadruplex. Only one target site in the whole human genome was selectively cleaved by the hybrid G-quadruplex. Such site-selective scission of DNA is central to gene manipulation for molecular biology, biotechnology, and therapy.

    17. siRNA Delivery

      Tumor-Homing Poly-siRNA/Glycol Chitosan Self-Cross-Linked Nanoparticles for Systemic siRNA Delivery in Cancer Treatment (pages 7203–7207)

      So Jin Lee, Dr. Myung Sook Huh, Seung Young Lee, Solki Min, Dr. Seulki Lee, Dr. Heebeom Koo, Dr. Jun-Uk Chu, Dr. Kyung Eun Lee, Dr. Hyesung Jeon, Dr. Yongseok Choi, Dr. Kuiwon Choi, Dr. Youngro Byun, Dr. Seo Young Jeong, Dr. Kinam Park, Dr. Kwangmeyung Kim and Dr. Ick Chan Kwon

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201201390

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      The condensed version: Thiolated glycol chitosan can form stable nanoparticles with polymerized siRNAs through charge–charge interactions and self-cross-linking (see scheme). This poly-siRNA/glycol chitosan nanoparticles (psi-TGC) provided sufficient in vivo stability for systemic delivery of siRNAs. Knockdown of tumor proteins by psi-TGC resulted in a reduction in tumor size and vascularization.

      Corrected by:

      Corrigendum: Corrigendum: Tumor-Homing Poly-siRNA/Glycol Chitosan Self-Cross-Linked Nanoparticles for Systemic siRNA Delivery in Cancer Treatment

      Vol. 51, Issue 47, 11661, Article first published online: 14 NOV 2012

    18. Supramolecular Chemistry

      Europium-Directed Self-Assembly of a Luminescent Supramolecular Gel from a Tripodal Terpyridine-Based Ligand (pages 7208–7212)

      Dr. Oxana Kotova, Dr. Ronan Daly, Dr. Cidália M. G. dos Santos, Dr. Markus Boese, Prof. Paul E. Kruger, Prof. John J. Boland and Prof. Thorfinnur Gunnlaugsson

      Article first published online: 11 JUN 2012 | DOI: 10.1002/anie.201201506

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      EuIII, the last piece in the puzzle: Europium-induced self-assembly of ligands having a C3-symmetrical benzene-1,3,5-tricarboxamide core results in the formation of luminescent gels. Supramolecular polymers are formed through hydrogen bonding between the ligands. The polymers are then brought together into the gel assembly through the coordination of terpyridine ends by EuIII ions (blue dashed arrow: distance between two ligands in the strand direction).

    19. Pt Electrocatalysts

      Self-Supported Interconnected Pt Nanoassemblies as Highly Stable Electrocatalysts for Low-Temperature Fuel Cells (pages 7213–7216)

      Dr. Bao Yu Xia, Wan Theng Ng, Hao Bin Wu, Prof. Xin Wang and Prof. Xiong Wen (David) Lou

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201201553

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      In it for the long haul: Clusters of Pt nanowires (3D Pt nanoassemblies, Pt NA) serve as an electrocatalyst for low-temperature fuel cells. These Pt nanoassemblies exhibit remarkably high stability following thousands of voltage cycles (see graph) and good catalytic activity, when compared with a commercial Pt catalyst and 20 % wt Pt catalyst supported on carbon black (20 % Pt/CB).

    20. Metallopeptides

      Hybrid Organic–Inorganic Inhibitors of a PDZ Interaction that Regulates the Endocytic Fate of CFTR (pages 7217–7220)

      Rituparna Kundu, Dr. Patrick R. Cushing, Dr. Brian V. Popp, Yu Zhao, Prof. Dean R. Madden and Prof. Zachary T. Ball

      Article first published online: 14 JUN 2012 | DOI: 10.1002/anie.201202291

      Thumbnail image of graphical abstract

      Together strong: Cooperative binding of organic (see picture, red) and inorganic fragments provides a strategy for the potent inhibition of protein–protein interactions. By targeting specific Lewis basic side chains in peripheral regions of the binding site for coordination to a rhodium(II) center, the affinity of otherwise weak ligands is improved.

    21. Topological Insulators

      Topological Insulators from a Chemist’s Perspective (pages 7221–7225)

      Lukas Müchler, Dr. Haijun Zhang, Dr. Stanislav Chadov, Dr. Binghai Yan, Dr. Frederick Casper, Prof. Jürgen Kübler, Prof. Shou-Cheng Zhang and Prof. Claudia Felser

      Article first published online: 8 JUN 2012 | DOI: 10.1002/anie.201202480

      Thumbnail image of graphical abstract

      Heavy stuff: Topological insulators are formed of heavy atoms and host special surface or edge states. The electronic structure is characterized by a Dirac cone within a bulk band gap (see picture) that is generated by strong spin–orbit coupling. A chemist's perspective in terms of bonds, bands, symmetry, and nuclear charge is provided.

    22. Catalysis

      Redox Reactions in Palladium Catalysis: On the Accelerating and/or Inhibiting Effects of Copper and Silver Salt Additives in Cross-Coupling Chemistry Involving Electron-rich Phosphine Ligands (pages 7226–7230)

      Marialuisa Aufiero, Fabien Proutiere and Prof. Dr. Franziska Schoenebeck

      Article first published online: 11 JUN 2012 | DOI: 10.1002/anie.201202504

      Thumbnail image of graphical abstract

      Challenging a catalytic cycle: Pd0 catalysts are readily oxidized by Cu and Ag salts to give dinuclear PdI complexes and CuI or AgI cubanes (see scheme). The reactivities of the resulting PdI dimers are consistent with several observations of additive effects in cross-coupling chemistry. The results indicate the possibility for alternative catalytic cycles involving dinuclear PdI complexes over the currently accepted synergistic cycles involving Pd0/PdII intermediates and Cu or Ag.

    23. Supramolecular Crystal Engineering

      Oligomeric Pseudorotaxanes Adopting Infinite-Chain Lattice Superstructures (pages 7231–7235)

      Dr. Zhixue Zhu, Hao Li, Dr. Zhichang Liu, Juying Lei, Dr. Huacheng Zhang, Dr. Youssry Y. Botros, Charlotte L. Stern, Dr. Amy A. Sarjeant, Prof. J. Fraser Stoddart and Prof. Howard M. Colquhoun

      Article first published online: 14 JUN 2012 | DOI: 10.1002/anie.201202513

      Thumbnail image of graphical abstract

      It's just an illusion: Above a critical chain length, where oligomers contain five or more recognition units, apparently infinite donor–acceptor polypseudorotaxanes are formed in the solid state (see picture). X-ray crystallographic analyses of three different examples have shown that although the oligomeric chains are undoubtedly discrete and monodisperse, they nevertheless appear to be infinite in the crystal.

    24. Electronic Structure

      Clar’s Aromatic Sextet and π-Electron Distribution in Nanographene (pages 7236–7241)

      Dr. Shintato Fujii and Prof. Toshiaki Enoki

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201202560

      Thumbnail image of graphical abstract

      Cut into pieces: The π-electron distribution in nanographene fragments isolated between oxidized graphene areas is investigated using scanning probe microscopy (see picture). The edge-shape-dependent localization and migration of the Clar sextet explains the observed π-state distributions and enables investigation of the electronic properties.

    25. Functionalizable Directing Groups

      Rhodium(III)-Catalyzed C[BOND]H Activation of Arenes Using a Versatile and Removable Triazene Directing Group (pages 7242–7245)

      Chengming Wang, Hu Chen, Zhaofeng Wang, Jiean Chen and Prof. Dr. Yong Huang

      Article first published online: 25 JUN 2012 | DOI: 10.1002/anie.201203230

      Thumbnail image of graphical abstract

      Diverse opportunities: A Rhodium(III)-catalyzed ortho-selective olefination of arenes using a novel triazene as a directing group is reported. This method exhibits substantial post-functionalization synthetic versatility, overcoming a vital limitation in Cmath image[BOND]H activation/functionalization products: restricted structural diversity.

    26. Post-Translational Modifications

      Site-Specific Incorporation of ε-N-Crotonyllysine into Histones (pages 7246–7249)

      Dr. Chan Hyuk Kim, Mingchao Kang, Dr. Hak Joong Kim, Dr. Abhishek Chatterjee and Prof. Peter G. Schultz

      Article first published online: 11 JUN 2012 | DOI: 10.1002/anie.201203349

      Thumbnail image of graphical abstract

      A novel post-translationally modified amino acid, crotonyllysine (Kcr), was genetically incorporated into proteins in bacterial and mammalian cells using an evolved pyrrolysyl-tRNA/synthetase-tRNA pair. The ability to produce histones with homogenous, site-specific Kcr modifications will be valuable in elucidating the biological role of this recently identified post-translational modification.

    27. Oxidative Amidation

      Manganese Oxide Promoted Liquid-Phase Aerobic Oxidative Amidation of Methylarenes to Monoamides Using Ammonia Surrogates (pages 7250–7253)

      Dr. Ye Wang, Dr. Kazuya Yamaguchi and Prof. Dr. Noritaka Mizuno

      Article first published online: 11 JUN 2012 | DOI: 10.1002/anie.201203098

      Thumbnail image of graphical abstract

      In the presence of amorphous MnO2, various methylarenes (even with two or more methyl groups) could be selectively converted into the corresponding primary monoamides in moderate to high yields. The observed catalysis was truly heterogeneous, and the retrieved amorphous MnO2 catalyst could be reused without an appreciable loss of its catalytic performance.

    28. Drug Delivery

      Glucocorticoid-Loaded Core-Cross-Linked Polymeric Micelles with Tailorable Release Kinetics for Targeted Therapy of Rheumatoid Arthritis (pages 7254–7258)

      Dr. Bart J. Crielaard, Dr. Cristianne J. F. Rijcken, Dr. Lingdong Quan, Steffen van der Wal, Isil Altintas, Martin van der Pot, Dr. John A. W. Kruijtzer, Prof. Rob M. J. Liskamp, Dr. Raymond M. Schiffelers, Dr. Cornelus F. van Nostrum, Prof. Wim E. Hennink, Prof. Dong Wang, Dr. Twan Lammers and Prof. Gert Storm

      Article first published online: 12 JUN 2012 | DOI: 10.1002/anie.201202713

      Thumbnail image of graphical abstract

      Polymerizable and hydrolytically cleavable dexamethasone (DEX, red dot in picture) derivatives were covalently entrapped in core-cross-linked polymeric micelles that were prepared from a thermosensitive block copolymer (yellow and gray building block). By varying the oxidation degree of the thioether in the drug linker, the release rate of DEX could be controlled. The DEX-loaded micelles were used for efficient treatment of inflammatory arthritis in two animal models.

    29. Radical-Cation Reactions

      Metal- and Chemical-Oxidant-Free C[BOND]H/C[BOND]H Cross-Coupling of Aromatic Compounds: The Use of Radical-Cation Pools (pages 7259–7262)

      Tatsuya Morofuji, Dr. Akihiro Shimizu and Prof. Jun-ichi Yoshida

      Article first published online: 11 JUN 2012 | DOI: 10.1002/anie.201202788

      Thumbnail image of graphical abstract

      Pool and couple: A method for oxidative C[BOND]H/C[BOND]H cross-coupling has been developed using “radical-cation pools”. Aromatic compounds react with aryl radical cations, which are generated and accumulated by low-temperature electrolysis (see scheme). This method avoids both the nonselective oxidation of substrates and oxidation of products and effects the C[BOND]H/C[BOND]H cross-coupling of aromatic compounds without metal complexes and chemical oxidants.

    30. Synthetic Methods

      Highly Diastereoselective Construction of Acyclic Systems with Two Adjacent Quaternary Stereocenters by Allylation of Ketones (pages 7263–7266)

      Prof. Dr. Takeshi Takeda, Masanori Yamamoto, Satoshi Yoshida and Dr. Akira Tsubouchi

      Article first published online: 8 JUN 2012 | DOI: 10.1002/anie.201202808

      Thumbnail image of graphical abstract

      Unsymmetrical ketones and allyltitanocenes generated by the desulfurizative titanation of γ,γ-disubstituted allyl phenyl sulfides react under highly diastereoselective construction of adjacent quaternary stereocenters (see scheme; RL=large group, RS=small group). The title reaction is stereospecific: the anti- and syn-homoallylic alcohols are obtained by the reaction of E- and Z-allylic sulfides, respectively.

    31. Hollow Structures

      Unusual Formation of Single-Crystal Manganese Sulfide Microboxes Co-mediated by the Cubic Crystal Structure and Shape (pages 7267–7270)

      Dr. Lei Zhang, Dr. Liang Zhou, Hao Bin Wu, Prof. Rong Xu and Prof. Xiong Wen (David) Lou

      Article first published online: 8 JUN 2012 | DOI: 10.1002/anie.201202877

      Thumbnail image of graphical abstract

      Kept cubic: MnS microboxes, which act as an anode material for lithium ion batteries, are synthesized by a simple H2S gas sulfidation approach (TEM images show porous and hollow microcubes and a microbox). The formation of the single crystals is aided by the intrinsic cubic crystal structure and the nearly cubic shape of the MnCO3 precursor.

    32. Natural Product Synthesis

      Concise Total Synthesis of (−)-Myxalamide A (pages 7271–7274)

      Kazuhiro Fujita, Dr. Ryosuke Matsui, Dr. Takahiro Suzuki and Prof. Dr. Susumu Kobayashi

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201203093

      Thumbnail image of graphical abstract

      The MIDA touch: A concise and highly convergent protecting-group-free total synthesis of (−)-myxalamide A involves a stereoselective vinylogous Mukaiyama aldol reaction of a vinylketene silyl N,O-acetal, together with a one-pot Stille/Suzuki–Miyaura cross-coupling reaction using Burke's N-methyliminodiacetic acid (MIDA) boronate to connect left- and right-hand fragments of the molecule (see scheme).

    33. Polyoxometalate Catalysis

      Chemo- and Regioselective Direct Hydroxylation of Arenes with Hydrogen Peroxide Catalyzed by a Divanadium-Substituted Phosphotungstate (pages 7275–7278)

      Dr. Keigo Kamata, Taiyo Yamaura and Prof. Dr. Noritaka Mizuno

      Article first published online: 8 JUN 2012 | DOI: 10.1002/anie.201201605

      Thumbnail image of graphical abstract

      Peroxide in, phenol out: The catalyst [γ-PW10O38V2(μ-OH)2]3− showed high activity in the hydroxylation of various aromatic compounds with aqueous H2O2. The system was regioselective, producing para-phenols from monosubstituted benzene derivatives. Furthermore, alkylarenes with reactive side-chain Cmath image[BOND]H bonds could be chemoselectively hydroxylated without significant formation of side-chain oxygenated products.

    34. Organocatalysis

      A Catalytic Asymmetric Ugi-type Reaction With Acyclic Azomethine Imines (pages 7279–7281)

      Dr. Takuya Hashimoto, Hidenori Kimura, Yu Kawamata and Prof. Dr. Keiji Maruoka

      Article first published online: 12 JUN 2012 | DOI: 10.1002/anie.201201905

      Thumbnail image of graphical abstract

      An unconventional Ugi: A catalytic asymmetric Ugi-type reaction can be realized by use of N′-alkylbenzohydrazide, instead of a conventional amine, in the presence of an axially chiral dicarboxylic acid. The reaction proceeds through a key acyclic azomethine imine intermediate, which has recently emerged as a promising electrophile in asymmetric catalysis.

    35. Cascade Reactions

      An Organocatalytic Cascade Approach toward Polysubstituted Quinolines and Chiral 1,4-Dihydroquinolines–Unanticipated Effect of N-Protecting Groups (pages 7282–7286)

      Xinshuai Zhang, Xixi Song, Prof. Dr. Hao Li, Dr. Shilei Zhang, Xiaobei Chen, Prof. Dr. Xinhong Yu and Prof. Dr. Wei Wang

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201202161

      Thumbnail image of graphical abstract

      A matter of protection: The outcome of a divergent organocatalytic aza-Michael/aldol cascade process toward quinolines and 1,4-dihydroquinolines depends on the choice of the N-protecting group (see scheme; TEA=triethylamine, TMS=trimethylsilyl). Use of an electron-donating sulfonyl group results in an unanticipated aza-Michael/aldol/aromatization cascade to give polysubstituted quinolines (right). In contrast, chiral 1,4-dihydroquinolines are obtained with an electron-withdrawing sulfonyl group (left).

    36. Micelle Formation

      Facile Synthesis of Multimeric Micelles (pages 7287–7291)

      Ung Yeol Lee, Nam Muk Oh, Dong Sup Kwag, Prof. Dr. Kyung Taek Oh, Prof. Dr. Young Taik Oh, Prof. Dr. Yu Seok Youn and Prof. Dr. Eun Seong Lee

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201202190

      Thumbnail image of graphical abstract

      Bringing it all together: Synthesis of a dimeric micelle (see scheme) is shown to produce specifically linked Janus-like micelles. The reaction conditions for dimeric micelle formation were optimized and the resulting micelles characterized. Trimeric, tetrameric, and multimeric micelles were also synthesized using the same technique.

    37. Quinolines

      Palladium-Catalyzed Sequential Formation of C[BOND]C Bonds: Efficient Assembly of 2-Substituted and 2,3-Disubstituted Quinolines (pages 7292–7296)

      Xiaochen Ji, Huawen Huang, Yibiao Li, Huoji Chen and Prof. Dr. Huanfeng Jiang

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201202412

      Thumbnail image of graphical abstract

      A series of substituted quinolines was prepared from arylamines, aldehydes, and terminal olefins (see scheme). The palladium-catalyzed sequential formation of C[BOND]C bonds proceeds smoothly with both electron-deficient and electron-rich olefins. When acrylic acid is used as terminal olefin, decarboxylation occurs to provide 2-substituted quinolines.

    38. Laser Spectroscopy

      Ultraviolet–Ultraviolet Hole Burning Spectroscopy in a Quadrupole Ion Trap: Dibenzo[18]crown-6 Complexes with Alkali Metal Cations (pages 7297–7300)

      Chang Min Choi, Dae Ho Choi, Prof. Jiyoung Heo, Prof. Nam Joon Kim and Prof. Seong Keun Kim

      Article first published online: 11 JUN 2012 | DOI: 10.1002/anie.201202640

      Thumbnail image of graphical abstract

      Conformation selective: A new technique of ultraviolet–ultraviolet hole burning spectroscopy that can be applied to ions stored in a quadrupole ion trap (QIT) is developed and used to obtain the conformation-selective electronic spectra of dibenzo[18]crown-6 complexes with alkali metal cations (M+, see picture; F+=fragment).

    39. N-Heterocycles

      Access to Electron-Rich Arene-Fused Hexahydroquinolizinones through a Gold-Catalysis-Initiated Cascade Process (pages 7301–7304)

      Dr. Lianzhu Liu and Prof. Dr. Liming Zhang

      Article first published online: 12 JUN 2012 | DOI: 10.1002/anie.201203303

      Thumbnail image of graphical abstract

      Golden Cascade: With a tethered, electron-rich arene as the internal nucleophile, a gold-catalyzed amide cyclization to an alkyne initiates a cascade process that ends with a Ferrier rearrangement. Electron-rich arene-bearing hexahydroquinolizin-2-ones are formed in good yields and can be converted into indole alkaloids in only a few steps.

    40. Homogeneous Catalysis

      Cmath image[BOND]H Bond Activation Triggered by Formation of Metallacycles: Rhodium(I)-Catalyzed Cyclopropanation/Cyclization of Allenynes (pages 7305–7308)

      Dr. Yoshihiro Oonishi, Yoshitaka Kitano and Prof. Dr. Yoshihiro Sato

      Article first published online: 27 JUN 2012 | DOI: 10.1002/anie.201203772

      Thumbnail image of graphical abstract

      Giving direction: An Cmath image[BOND]H bond activation directed by a rhodacycle intermediate has been found to occur in a RhI-catalyzed reaction between an allene moiety having a tert-butyl substituent, and tethered alkynes. Cyclic compounds containing a cyclopropane ring were obtained in good to high yields (up to 92%).

    41. Asymmetric Catalysis

      Catalytic Dynamic Kinetic Resolutions with N-Heterocyclic Carbenes: Asymmetric Synthesis of Highly Substituted β-Lactones (pages 7309–7313)

      Daniel T. Cohen, Dr. Chad C. Eichman, Eric M. Phillips, Emily R. Zarefsky and Prof. Karl A. Scheidt

      Article first published online: 14 JUN 2012 | DOI: 10.1002/anie.201203382

      Thumbnail image of graphical abstract

      New DKR type: An N-heterocyclic carbene (NHC)-catalyzed dynamic kinetic resolution of racemic α-substituted β-keto esters has been developed. This method relies on the epimerization of an NHC-enol intermediate before subsequent aldol/acylation events. Highly substituted β-lactones are produced in good yield with good to excellent selectivities (see scheme).

      Corrected by:

      Corrigendum: Corrigendum: Catalytic Dynamic Kinetic Resolutions with N-Heterocyclic Carbenes: Asymmetric Synthesis of Highly Substituted β-Lactones

      Vol. 52, Issue 20, 5203, Article first published online: 3 MAY 2013

    42. Diastereodivergent De-epimerization in Catalytic Asymmetric Allylic Alkylation (pages 7314–7317)

      Dr. Davide Audisio, Dr. Marco Luparia, Maria Teresa Oliveira, Dina Klütt and Dr. Nuno Maulide

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201202853

      Thumbnail image of graphical abstract

      Diastereomers made to order: In an unprecedented ligand-controlled process a racemic mixture of four stereoisomers can be converted with high selectivity into each one of the diastereomers of the product, at will (see scheme). The mechanism of this deracemization of epimers, that is, a de-epimerization, was also studied.

    43. C[BOND]H Activation

      Mild Rhodium(III)-Catalyzed C[BOND]H Activation and Intermolecular Annulation with Allenes (pages 7318–7322)

      Dr. Honggen Wang and Prof. Dr. Frank Glorius

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201201273

      Thumbnail image of graphical abstract

      All(enes) great! A novel RhIII-catalyzed oxidative coupling with allenes under mild conditions provides heterocycles with exocyclic double bonds. This reaction features low catalyst loadings, high regio- and stereoselectivity, and excellent substrate scope. The products were derivatized and preliminary mechanistic studies were conducted.

    44. Catalyzed CO2 Reduction

      Deoxygenative Reduction of Carbon Dioxide to Methane, Toluene, and Diphenylmethane with [Et2Al]+ as Catalyst (pages 7323–7326)

      Dr. Manish Khandelwal and Prof. Dr. Rudolf J. Wehmschulte

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201201282

      Thumbnail image of graphical abstract

      The strong Lewis acid [Et2Al]+ catalyzes the reduction of carbon dioxide with hydrosilanes under mild conditions to methane. In benzene solution, the side products toluene and diphenylmethane are also obtained through Lewis acid catalyzed benzene alkylation by reaction intermediates.

    45. Glycomimetics

      Sialyl Lewisx: A “Pre-Organized Water Oligomer”? (pages 7327–7331)

      Dr. Florian P. C. Binder, Dr. Katrin Lemme, Roland C. Preston and Prof. Dr. Beat Ernst

      Article first published online: 2 JUL 2012 | DOI: 10.1002/anie.201202555

      Thumbnail image of graphical abstract

      Organized and released: Sialyl Lewisx (sLex) represents a “pre-organized water oligomer”, that is, a surrogate for clustered water molecules attached to a scaffold. The impetus for sLex binding to E-selectin is shown to be the high degree of pre-organization allowing an array of directed hydrogen bonds, and the entropic benefit of the release of water molecules from the large binding interface to bulk water (see picture).

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      Article first published online: 11 JUL 2012 | DOI: 10.1002/anie.201290055

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