Angewandte Chemie International Edition

Cover image for Vol. 48 Issue 50

December 7, 2009

Volume 48, Issue 50

Pages 9377–9565

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Obituary
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. Cover Picture: Gemini-Surfactant-Directed Self-Assembly of Monodisperse Gold Nanorods into Standing Superlattices (Angew. Chem. Int. Ed. 50/2009) (page 9377)

      Andrés Guerrero-Martínez, Jorge Pérez-Juste, Enrique Carbó-Argibay, Gloria Tardajos and Luis M. Liz-Marzán

      Version of Record online: 11 NOV 2009 | DOI: 10.1002/anie.200905605

      Thumbnail image of graphical abstract

      Self-assembled two- and three-dimensional highly ordered aggregates of standing gold nanorods were obtained over unprecedentedly large superlattice domains. In their Communication on page 9484 ff., A. Guerrero-Martínez, L. M. Liz-Marzán, and co-workers report how the use of gemini surfactants was crucial for the growth of monodisperse nanorods and induction of the self-assembled structures into extended superlattices, which also display anisotropic optical response.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Obituary
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. Inside Cover: Design and Synthesis of a Homogeneous Erythropoietin Analogue with Two Human Complex-Type Sialyloligosaccharides: Combined Use of Chemical and Bacterial Protein Expression Methods (Angew. Chem. Int. Ed. 50/2009) (page 9378)

      Kiriko Hirano, Derek Macmillan, Katsunari Tezuka, Takashi Tsuji and Yasuhiro Kajihara

      Version of Record online: 11 NOV 2009 | DOI: 10.1002/anie.200905761

      Thumbnail image of graphical abstract

      Bioengineering of proteins using mammalian cells has facilitated the development of potential pharmaceutical erythropoietins (EPOs) that bear N-linked oligosaccharides. In their Communication on page 9557 ff., Y. Kajihara and co-workers report the chemical synthesis of a homogeneous bioactive EPO analogue, which was prepared by native chemical ligation between a synthetic glycopeptide-α-thioester with two complex-type sialyloligosaccharides and a large polypeptide chain, obtained by expression in E. coli.

  3. Graphical Abstract

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Obituary
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. You have free access to this content
      Palladium-Catalyzed Hydroxylation of Aryl Halides under Ambient Conditions (page 9391)

      Alexey G. Sergeev, Thomas Schulz, Christian Torborg, Anke Spannenberg, Helfried Neumann and Matthias Beller

      Version of Record online: 30 NOV 2009 | DOI: 10.1002/anie.200990250

      This article corrects:

      Palladium-Catalyzed Hydroxylation of Aryl Halides under Ambient Conditions1

      Vol. 48, Issue 41, 7595–7599, Version of Record online: 8 SEP 2009

  5. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Obituary
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. Gérard Férey (pages 9398–9400)

      Version of Record online: 15 OCT 2009 | DOI: 10.1002/anie.200904041

      Thumbnail image of graphical abstract

      “If I could be anyone for a day, I would be the conductor of a symphonic orchestra. When I was eighteen I wanted to be a teacher. …” This and more about Gérard Férey can be found on page 9398.

  7. Obituary

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Obituary
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. Ralph F. Hirschmann (19222009) (pages 9402–9403)

      Luis Moroder

      Version of Record online: 4 NOV 2009 | DOI: 10.1002/anie.200905975

  8. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Obituary
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. Ab Initio Molecular Dynamics. Basic Theory and Advanced Methods. By Dominik Marx and Jürg Hutter. (pages 9404–9405)

      Saman Alavi

      Version of Record online: 30 NOV 2009 | DOI: 10.1002/anie.200904748

      Thumbnail image of graphical abstract

      Cambridge University Press 2009. 578 pp., hardcover £ 45.00.—ISBN 978-0521898638

  9. Highlights

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

      Evolution of DNA Origami (pages 9406–9408)

      Álvaro Somoza

      Version of Record online: 17 NOV 2009 | DOI: 10.1002/anie.200904802

      Thumbnail image of graphical abstract

      DNA folding as an extended art form: Long strands of DNA can be folded in a controlled manner to yield 3D shapes. Moreover, twisted and curved shapes can be created with excellent control (see schematic representation). The key to these developments is the use of Holliday junctions, which connect different parts of the array and also create tension in the honeycomb system so that the DNA structure is forced to fold into the desired shape.

    2. Nitrogen Radicals

      N2.3−: Filling a Gap in the N2n Series (pages 9409–9411)

      Wolfgang Kaim and Biprajit Sarkar

      Version of Record online: 7 NOV 2009 | DOI: 10.1002/anie.200904968

      Thumbnail image of graphical abstract

      The unexpected stability of the exotic N2.3− species has been observed in its complexes with Dy3+ and Y3+. The three-electron reduction product of N2 is isoelectronic with superoxide O2.− (see scheme) and is a possible bound intermediate in the conversion of N2 into NH3.

  10. Minireview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Obituary
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. Palladium(IV) Catalysis

      High-Oxidation-State Palladium Catalysis: New Reactivity for Organic Synthesis (pages 9412–9423)

      Kilian Muñiz

      Version of Record online: 30 OCT 2009 | DOI: 10.1002/anie.200903671

      Thumbnail image of graphical abstract

      The higher, the better! The emergence in recent years of catalysis with high-oxidation-state palladium complexes has enabled the functionalization of alkyl and aryl compounds in a series of new reactions (see general scheme). Reaction processes and mechanistic aspects of these catalytic transformations are discussed in this Minireview.

  11. Review

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

      The Renaissance of α-Methylene-γ-butyrolactones: New Synthetic Approaches (pages 9426–9451)

      Russell R. A. Kitson, Alessia Millemaggi and Richard J. K. Taylor

      Version of Record online: 24 NOV 2009 | DOI: 10.1002/anie.200903108

      Thumbnail image of graphical abstract

      Flower power: The structures, biological activities, and biosynthesis of α-methylene-γ-butyrolactone and α-alkylidene-γ-butyrolactone natural products—which are found, for example, in arnica, feverfew, and, peony—are reviewed, as are recent synthetic approaches.

  12. Communications

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

      Unfolded-State Structure and Dynamics Influence the Fibril Formation of Human Prion Protein (pages 9452–9456)

      Christian Gerum, Robert Silvers, Julia Wirmer-Bartoschek and Harald Schwalbe

      Version of Record online: 30 OCT 2009 | DOI: 10.1002/anie.200903771

      Thumbnail image of graphical abstract

      Rigid bridges: NMR studies of the unfolded state (U) of the human prion protein (PrP) show that in the oxidized form the native disulfide bridge between two cysteine residues rigidifies the surrounding amino acids. This area is a hotspot region of the protein in terms of disease-related mutations that promote aggregation and formation of the abnormal “scrapie” form (PrPSc).

    2. Porous Organic Frameworks

      Targeted Synthesis of a Porous Aromatic Framework with High Stability and Exceptionally High Surface Area (pages 9457–9460)

      Teng Ben, Hao Ren, Shengqian Ma, Dapeng Cao, Jianhui Lan, Xiaofei Jing, Wenchuan Wang, Jun Xu, Feng Deng, Jason M. Simmons, Shilun Qiu and Guangshan Zhu

      Version of Record online: 17 NOV 2009 | DOI: 10.1002/anie.200904637

      Thumbnail image of graphical abstract

      Diamonds are forever: A diamond-like framework in which the C–C bonds are replaced with rigid phenyl rings (see picture) is not only structurally stable but also has a large internal surface area. This porous aromatic framework (PAF-1) demonstrates high uptake capacities of hydrogen and carbon dioxide as well as benzene and toluene vapors, and has an unprecedented surface area of 7100 m2 g−1.

    3. Metal–Organic Nanotubes

      Self-Assembled Arrays of Single-Walled Metal–Organic Nanotubes (pages 9461–9464)

      Tzuoo-Tsair Luo, Huang-Chun Wu, Yu-Chen Jao, Sheng-Ming Huang, Tien-Wen Tseng, Yuh-Sheng Wen, Gene-Hsiang Lee, Shie-Ming Peng and Kuang-Lieh Lu

      Version of Record online: 10 NOV 2009 | DOI: 10.1002/anie.200904501

      Thumbnail image of graphical abstract

      Dragon's lair: A large, single-walled metal–organic nanotube (MONT) with an exterior diameter of up to 3.2 nm and an internal channel diameter of 1.4 nm is presented. The tube can be depicted as hexastranded helices consisting of three right-handed and three left-handed helical chains, and resembles a rolled-up dragon column (see picture). The MONTs are held together by alkaline ions to form unique nanotubular arrays.

    4. Self-Assembly

      Confining Molecules within Aqueous Coordination Nanoparticles by Adaptive Molecular Self-Assembly (pages 9465–9468)

      Ryuhei Nishiyabu, Carole Aimé, Ryosuke Gondo, Takao Noguchi and Nobuo Kimizuka

      Version of Record online: 17 NOV 2009 | DOI: 10.1002/anie.200904124

      Thumbnail image of graphical abstract

      Dying on the inside: Functional dye molecules can be adaptively encapsulated in coordination nanoparticles (CNPs) of nucleotides and lanthanide ions in the course of their formation in water (see picture). Dyes confined in CNPs are conformationally restricted and surprisingly stable against molecular oxygen. These properties should be favorable for the development of light-harvesting CNPs.

    5. Prion Misfolding

      Cholesterol Secosterol Adduction Inhibits the Misfolding of a Mutant Prion Protein Fragment that Induces Neurodegeneration (pages 9469–9472)

      Johanna C. Scheinost, Daniel P. Witter, Grant E. Boldt, John Offer and Paul Wentworth Jr.

      Version of Record online: 6 NOV 2009 | DOI: 10.1002/anie.200904524

      Thumbnail image of graphical abstract

      Aldehyde is critical: Atheronal-B, a cholesterol secosterol aldehyde (see structure), completely inhibits the misfolding of a prion protein fragment from its α to β form through a mechanism that involves adduction to the protein. This result offers a fresh view of lipid aldehyde-induced protein misfolding and provides a promising molecular scaffold on which to develop potential prion disease therapeutics.

    6. Water Oxidation

      Catalytic and Surface-Electrocatalytic Water Oxidation by Redox Mediator–Catalyst Assemblies (pages 9473–9476)

      Javier J. Concepcion, Jonah W. Jurss, Paul G. Hoertz and Thomas J. Meyer

      Version of Record online: 10 NOV 2009 | DOI: 10.1002/anie.200901279

      Thumbnail image of graphical abstract

      All-in-one assemblies containing single-site water oxidation catalysts (red and blue) and redox mediators (green and blue) act as stable, robust catalysts toward water oxidation, both in solution and anchored to metal oxide surfaces by phosphonate linkers on the mediator. More than 28 000 turnovers have been achieved with >95 % Faradaic efficiency for oxygen production without reduced catalytic activity.

    7. Nanoparticles

      Making Use of Bond Strength and Steric Hindrance in Nanoscale “Synthesis” (pages 9477–9480)

      Yanhu Wei, Kyle J. M. Bishop, Jiwon Kim, Siowling Soh and Bartosz A. Grzybowski

      Version of Record online: 7 NOV 2009 | DOI: 10.1002/anie.200903864

      Thumbnail image of graphical abstract

      The chemical concepts of bond strength and steric hindrance are extended to the nanoscale to control “reactions” of composite nanoparticles into primitive “nanomolecules” of well-defined shapes and sizes. The progress of these nanoscale transformations is controlled by an interplay between the strength of bonding between particles' reactive domains and the entropic effects because of the bulkiness of the unreactive parts.

    8. RNA Probes

      An Activatable siRNA Probe: Trigger-RNA-Dependent Activation of RNAi Function (pages 9481–9483)

      Hiroki Masu, Atsushi Narita, Takeshi Tokunaga, Masayoshi Ohashi, Yasuhiro Aoyama and Shinsuke Sando

      Version of Record online: 10 NOV 2009 | DOI: 10.1002/anie.200903925

      Thumbnail image of graphical abstract

      Catch and release: A hairpin-shaped sense strand (red)/antisense strand (blue) siRNA probe was designed to be activated by a trigger RNA molecule. In the presence of the trigger RNA, clear OFF-to-ON switching of RNAi activity was observed with high sequence dependency (see schematic illustration).

    9. Nanorod Assembly

      Gemini-Surfactant-Directed Self-Assembly of Monodisperse Gold Nanorods into Standing Superlattices (pages 9484–9488)

      Andrés Guerrero-Martínez, Jorge Pérez-Juste, Enrique Carbó-Argibay, Gloria Tardajos and Luis M. Liz-Marzán

      Version of Record online: 2 OCT 2009 | DOI: 10.1002/anie.200904118

      Thumbnail image of graphical abstract

      A super lattice: The title system allows the spontaneous formation of self-assembled 2D and 3D highly ordered aggregates of standing nanorods on large superlattice domains (see picture). The hexagonal close packing of nanorods perpendicular to the substrate resembles smectic-B liquid-crystalline phases. Optical characterization of the aggregates demonstrates their anisotropic optical response.

    10. Single-Molecule Magnets

      A Polynuclear Lanthanide Single-Molecule Magnet with a Record Anisotropic Barrier (pages 9489–9492)

      Po-Heng Lin, Tara J. Burchell, Liviu Ungur, Liviu F. Chibotaru, Wolfgang Wernsdorfer and Muralee Murugesu

      Version of Record online: 17 NOV 2009 | DOI: 10.1002/anie.200903199

      Thumbnail image of graphical abstract

      Magnetic measurements on a {Dy4} single-molecule magnet (SMM) with a defect-dicubane central core, synthesized using 1,2-bis(2-hydroxy-3-methoxybenzylidene) hydrazone and 3-methoxysalicylaldehyde hydrazone as chelating agents (see structure; yellow Dy, red O, blue N, green Cl), confirm SMM behavior and reveal hysteresis loops at 7 K. The anisotropic energy barrier of Ueff=170 K is the highest reported to date.

    11. Drug Delivery

      Genome-Free Viral Capsids as Multivalent Carriers for Taxol Delivery (pages 9493–9497)

      Wesley Wu, Sonny C. Hsiao, Zachary M. Carrico and Matthew B. Francis

      Version of Record online: 17 NOV 2009 | DOI: 10.1002/anie.200902426

      Thumbnail image of graphical abstract

      Delivery by Trojan horse: A water-soluble derivative of the chemotherapeutic agent taxol was synthesized with bioconjugation functionality and attached to capsids of the bacteriophage MS2 (see picture). The modified capsids retained their form and released taxol when incubated with MCF-7 cells. The resulting cell-viability levels were similar to those observed upon treatment with free taxol in solution.

    12. Energy Transfer

      Nanoscale Integration of Sensitizing Chromophores and Porphyrins with Bacteriophage MS2 (pages 9498–9502)

      Nicholas Stephanopoulos, Zachary M. Carrico and Matthew B. Francis

      Version of Record online: 17 NOV 2009 | DOI: 10.1002/anie.200902727

      Thumbnail image of graphical abstract

      Harnessing energy from within: Energy transfer from the inside to the outside of MS2 capsids modified by positioning fluorescent dyes and a photocatalytic zinc porphyrin on their surfaces (see picture) enabled sensitization of the porphyrin at multiple wavelengths and thus broad-spectrum catalytic activity.

    13. DNA Detection

      Nanoparticle-Based, Fluorous-Tag-Driven DNA Detection (pages 9503–9506)

      Min Hong, Xin Zhou, Zhiqiang Lu and Jin Zhu

      Version of Record online: 12 NOV 2009 | DOI: 10.1002/anie.200905267

      Thumbnail image of graphical abstract

      Tagging along: A DNA detection method has been developed that relies on the interfacial assembly of gold nanoparticles. The fluorous-tag-driven formation of nanoparticle networks (see scheme) at the gas/liquid, liquid/liquid, or solid/liquid interface is such that a single type of assembly architecture is suitable for an array of detection formats.

    14. Homogeneous Catalysis

      A Convenient and General Iron-Catalyzed Reduction of Amides to Amines (pages 9507–9510)

      Shaolin Zhou, Kathrin Junge, Daniele Addis, Shoubhik Das and Matthias Beller

      Version of Record online: 25 SEP 2009 | DOI: 10.1002/anie.200904677

      Thumbnail image of graphical abstract

      While the iron is hot: The first general and efficient iron-catalyzed reduction of secondary and tertiary amides into amines using polymethylhydrosiloxane (PMHS) has been developed (see scheme).

    15. Iron-Catalyzed Reduction

      Hydrosilane Reduction of Tertiary Carboxamides by Iron Carbonyl Catalysts (pages 9511–9514)

      Yusuke Sunada, Hiroko Kawakami, Tsuyoshi Imaoka, Yukihiro Motoyama and Hideo Nagashima

      Version of Record online: 10 NOV 2009 | DOI: 10.1002/anie.200905025

      Thumbnail image of graphical abstract

      Fox in the carboxamide: Reduction of tertiary carboxamides to their corresponding amines is catalyzed by [Fe(CO)5] or [Fe3(CO)12], using 1,1,3,3-tetramethyldisiloxane (TMDS) as the reducing agent. The reaction proceeds under either thermal or photochemical conditions. Unlike the hydrosilane reduction of amides using platinum or ruthenium catalysts, TMDS preferentially reduces a nitro group, even in the presence of competing amides.

    16. Heterogeneous Catalysis

      Hydrogen Dissociation by Gold Clusters (pages 9515–9518)

      Tadahiro Fujitani, Isao Nakamura, Tomoki Akita, Mitsutaka Okumura and Masatake Haruta

      Version of Record online: 12 NOV 2009 | DOI: 10.1002/anie.200905380

      Thumbnail image of graphical abstract

      The rate of H2–D2exchange increases in proportion to the inverse square of the mean diameter of gold particles supported on TiO2 (see picture), which indicates that hydrogen dissociation takes place on the perimeter interfaces between the gold and TiO2 and that the catalytic activity for H2 dissociation is correlated neither to a change in the fraction of edge or corner sites nor to a change in the electronic nature induced by the quantum size effect.

    17. Biomimetic Synthesis

      Total Synthesis of TK-57-164A, Isariotin F, and Their Putative Progenitor Isariotin E (pages 9519–9521)

      Jacob Y. Cha, Yaodong Huang and Thomas R. R. Pettus

      Version of Record online: 17 NOV 2009 | DOI: 10.1002/anie.200904716

      Thumbnail image of graphical abstract

      Keeping it simple: A simple strategy for the total synthesis of three complex natural products has been developed, while also confirming the putative generation of 1 and 2 from 3. The benefits of a simple dissymmetric 2,5-cyclohexadienone are illustrated and provide the foundation for rapid diastereoselective functionalization leading to the first total synthesis of these compounds.

    18. Peptide Binding

      Deprotonation of the Asp1[BOND]Ala2 Peptide Bond Induces Modification of the Dynamic Copper(II) Environment in the Amyloid-β Peptide near Physiological pH (pages 9522–9525)

      Christelle Hureau, Yannick Coppel, Pierre Dorlet, Pier Lorenzo Solari, Stéphanie Sayen, Emmanuel Guillon, Laurent Sabater and Peter Faller

      Version of Record online: 10 NOV 2009 | DOI: 10.1002/anie.200904512

      Thumbnail image of graphical abstract

      Premium bonds: The pH-dependent coordination of CuII to the Alzheimer′s disease amyloid-β peptide has been studied by NMR spectroscopy. Several equivalent ligands are in equilibrium for CuII binding near pH 6.6 and 8.7. Fewer conformers are detected at high pH, in line with a reshuffling of the CuII binding site induced by deprotonation of the Asp1[BOND]Ala2 peptide bond (see picture).

    19. Nucleoside Complexes

      The Charge-Transfer Band of an Oxidized Watson–Crick Guanosine–Cytidine Complex (pages 9526–9528)

      Amedeo Capobianco, Maurizio Carotenuto, Tonino Caruso and Andrea Peluso

      Version of Record online: 10 NOV 2009 | DOI: 10.1002/anie.200904305

      Thumbnail image of graphical abstract

      The hole truth: A low-energy band in the absorption spectrum of the oxidized Watson–Crick complex of guanosine and cytidine derivatives (see scheme) is attributed to charge-transfer localizing the hole from one-electron oxidation on the cytidine moiety. The band provides an estimate of the energy of one of the low-lying electronic states of oxidized duplex DNA.

    20. Sonochemistry

      Sonochemical Disproportionation of Carbon Monoxide in Water: Evidence for Treanor Effect during Multibubble Cavitation (pages 9529–9532)

      Sergey I. Nikitenko, Philippe Martinez, Tony Chave and Isabelle Billy

      Version of Record online: 17 NOV 2009 | DOI: 10.1002/anie.200904275

      Thumbnail image of graphical abstract

      A sound reaction: The ultrasonically driven disproportionation of CO in water causes formation of hydrated polymer of carbon suboxide (C3O2)n (see picture) enriched with a heavy 13C isotope. This finding indicates the presence of vibrationally excited CO molecules with a non-equilibrium Treanor distribution inside the cavitating bubble.

    21. Alkylation

      Enantioselective Gold-Catalyzed Allylic Alkylation of Indoles with Alcohols: An Efficient Route to Functionalized Tetrahydrocarbazoles (pages 9533–9537)

      Marco Bandini and Astrid Eichholzer

      Version of Record online: 10 NOV 2009 | DOI: 10.1002/anie.200904388

      Thumbnail image of graphical abstract

      Breaking the taboo: The direct use of allylic alcohols in catalytic and enantioselective Friedel–Crafts alkylation is described for the first time in the presence of chiral gold complexes. This intramolecular Friedel–Crafts reaction was used to prepare a broad range of functionalized tetrahydrocarbazoles (see scheme; X=Me, F, Br, Cl, OMe; R=Me, Et, tBu; R′=H, Me).

    22. Sustainable Gold Catalysis

      Efficient and Selective Room-Temperature Gold-Catalyzed Reduction of Nitro Compounds with CO and H2O as the Hydrogen Source (pages 9538–9541)

      Lin He, Lu-Cun Wang, Hao Sun, Ji Ni, Yong Cao, He-Yong He and Kang-Nian Fan

      Version of Record online: 17 NOV 2009 | DOI: 10.1002/anie.200904647

      Thumbnail image of graphical abstract

      Taking hydrogen from water: Gold catalysis enabled the selective reduction of nitro compounds under very mild conditions with a combination of H2O and CO as the reductant (see scheme). This environmentally friendly reaction proceeded in high yield and with high chemoselectivity in the presence of a wide range of functional groups.

    23. Cascade Reaction

      Construction of Fused Heterocyclic Architectures by Formal [4+1]/[3+2] Cycloaddition Cascade of Sulfur Ylides and Nitroolefins (pages 9542–9545)

      Liang-Qiu Lu, Fang Li, Jing An, Ji-Ji Zhang, Xiao-Lei An, Qiu-Lin Hua and Wen-Jing Xiao

      Version of Record online: 10 NOV 2009 | DOI: 10.1002/anie.200904766

      Thumbnail image of graphical abstract

      Under control: A formal [4+1]/[3+2] cycloaddition cascade of sulfur ylides and alkene-tethered nitroolefins has been developed, and provides an efficient synthesis of fused polycyclic heterocyclic compounds in good to excellent overall yields with excellent diastereocontrol (see scheme). A catalytic asymmetric variant of this reaction has also been disclosed.

    24. Enzymatic Synthesis

      Biocatalytic Friedel–Crafts Alkylation Using Non-natural Cofactors (pages 9546–9548)

      Harald Stecher, Martin Tengg, Bernhard J. Ueberbacher, Peter Remler, Helmut Schwab, Herfried Griengl and Mandana Gruber-Khadjawi

      Version of Record online: 6 NOV 2009 | DOI: 10.1002/anie.200905095

      Thumbnail image of graphical abstract

      A novel biocatalytic protocol for C[BOND]C bond formation is described and is an equivalent to Friedel–Crafts alkylation. S-Adenosyl-L-methionine (SAM), the major methyl donor for biological methylation catalyzed by methyltransferases (Mtases), can perform alkylations (see scheme). These enzymes can accept non-natural cofactors and transfer functionalities other than methyl onto aromatic substrates.

    25. Radical Reactions

      Radical Cyclization of α-Bromo Aluminum Acetals: An Easy Approach to γ-Lactols (pages 9549–9552)

      Anne Boussonnière, Fabrice Dénès and Jacques Lebreton

      Version of Record online: 10 NOV 2009 | DOI: 10.1002/anie.200905167

      Thumbnail image of graphical abstract

      Running rings around aluminum: An efficient procedure for radical cyclization of α-bromo esters is reported. Reduction of the esters by DIBAL-H at low temperature gives aluminum acetals, which are cyclized in the presence of nBu3SnH and Et3B (see scheme). These one-pot conditions lead to polysubstituted γ-lactols in high yields, and the mildness of the reaction conditions allows the preparation of acid-sensitive derivatives.

    26. C[BOND]H Bond Activation

      Copper as a Powerful Catalyst in the Direct Alkynylation of Azoles (pages 9553–9556)

      François Besselièvre and Sandrine Piguel

      Version of Record online: 9 NOV 2009 | DOI: 10.1002/anie.200904776

      Thumbnail image of graphical abstract

      Copper-bottomed catalysis! The direct alkynylation of azoles through a copper-based C[BOND]H bond activation, using alkynylbromides as the coupling partner, has been developed (see scheme). The method is very rapid, is functional-group tolerant, and provides a straightforward entry to diverse alkynyl heterocycles that is complementary to the Sonogashira reaction.

    27. Glycoprotein Synthesis

      Design and Synthesis of a Homogeneous Erythropoietin Analogue with Two Human Complex-Type Sialyloligosaccharides: Combined Use of Chemical and Bacterial Protein Expression Methods (pages 9557–9560)

      Kiriko Hirano, Derek Macmillan, Katsunari Tezuka, Takashi Tsuji and Yasuhiro Kajihara

      Version of Record online: 1 OCT 2009 | DOI: 10.1002/anie.200904376

      Thumbnail image of graphical abstract

      Highly expressive: Cell proliferation was observed with concentrations of an erythropoietin (EPO) analogue above 50 pg mL−1. The EPO analogue has two human complex-type sialyloligosaccharides (see picture) and was formed by the combined use of chemical synthesis and protein expression in E. coli. Both the 24- and 30-positions are glycosylated, but the two sialyloligosaccharides do not interfere with binding of the EPO analogue to a receptor.

  13. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Obituary
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. You have free access to this content

SEARCH

SEARCH BY CITATION