Angewandte Chemie International Edition

Cover image for Angewandte Chemie International Edition

June 27, 2011

Volume 50, Issue 27

Pages 5973–6181

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Cover Picture: Soluble Synthetic Analogues of Malaria Pigment: Structure of Mesohematin Anhydride and its Interaction with Chloroquine in Solution (Angew. Chem. Int. Ed. 27/2011) (page 5973)

      Prof.  D. Scott Bohle, Erin L. Dodd, Aaron J. Kosar, Lauren Sharma, Peter W. Stephens, Liliana Suárez and Dagobert Tazoo

      Article first published online: 7 JUN 2011 | DOI: 10.1002/anie.201103664

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      Transmission, invasion, digestion, crystallization, and reproduction are all critical parts of the life cycle of the malaria parasite. With the onset of drug-resistant strains, new antimalarial drugs are urgently needed, and all aspects of the parasite's unique lifecycle and biochemistry need to be exploited. D. S. Bohle, P. W. Stephens, et al. describe in their Communication on page 6151 ff. new soluble malaria pigment derivatives and characterize their interactions with the quinoline antimalarials.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Inside Cover: Hierarchical Selectivity in Fullerenes: Site-, Regio-, Diastereo-, and Enantiocontrol of the 1,3-Dipolar Cycloaddition to C70 (Angew. Chem. Int. Ed. 27/2011) (page 5974)

      Enrique E. Maroto, Dr. Abel de Cózar, Dr. Salvatore Filippone, Dr. Ángel Martín-Domenech, Prof. Dr. Margarita Suarez, Prof. Dr. Fernando P. Cossío and Prof. Dr. Nazario Martín

      Article first published online: 7 JUN 2011 | DOI: 10.1002/anie.201103579

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      Selectivity is still a major challenge in fullerene research. In their Communication on page 6060 ff. N. Martín, F. Cossío, and co-workers describe how the use of a suitable chiral catalyst controls the addition of fullerenes to both faces of a 1,3-dipole, thus determining the stereochemical outcome. The careful choice of the experimental conditions affords chiral [70]fullerene derivatives with unusually high site- and regioselectivity.

  3. Back Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Back Cover: Bioinspired Functionalization of Silica-Encapsulated Yeast Cells (Angew. Chem. Int. Ed. 27/2011)

      Dr. Sung Ho Yang, Eun Hyea Ko, Prof. Dr. Young Hwan Jung and Prof. Dr. Insung S. Choi

      Article first published online: 7 JUN 2011 | DOI: 10.1002/anie.201103446

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      Single-cell encapsulation with artificial inorganic shells can be coupled with shell-surface functionalization. In their Communication on page 6115 ff., I. S. Choi and co-workers report the individual encapsulation of living yeast cells within thiol-functionalized silica shells (yellow shells). The silica shells are functionalized with biotin (green), and then are either spatioselectively immobilized onto a defined surface or complexed with streptavidin in solution (brown).

  4. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Graphical Abstract: Angew. Chem. Int. Ed. 27/2011 (pages 5977–5987)

      Article first published online: 21 JUN 2011 | DOI: 10.1002/anie.201190053

  5. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Hans-Dieter Arndt (page 5994)

      Article first published online: 8 JUN 2011 | DOI: 10.1002/anie.201102744

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      “Guaranteed to make me laugh is a ridiculous accumulation of buzzwords. Science really can be fun at times! What I look for first in a publication are the figures …” This and more about Hans-Dieter Arndt can be found on page 5994.

  7. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Classics in Total Synthesis III. Further Targets, Strategies, Methods. By K. C. Nicolaou and Jason S. Chen. (pages 5995–5996)

      Dirk Menche and Sebastian Essig

      Article first published online: 30 MAY 2011 | DOI: 10.1002/anie.201103334

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      Wiley-VCH, Weinheim, 2011. 746 pp., softcover, € 79.00.—ISBN 978-3527329571

  8. Highlights

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

      Construction of Asymmetric Quaternary Carbon Centers with High Enantioselectivity (pages 5998–6000)

      Prof.  Masaki Shimizu

      Article first published online: 24 MAY 2011 | DOI: 10.1002/anie.201101720

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      Taking another path: Three different methods for the homologation of boronates have been developed by Aggarwal and co-workers in a powerful new approach to the enantioselective construction of quaternary carbon centers (see scheme; Bpin=pinacolatoboryl). The starting enantiomerically enriched tert-alkyl boronates can be prepared with excellent enantioselectivity.

    2. Supramolecular Chemistry

      Coordination Polymer Nanostructures (pages 6001–6003)

      Prof. Antonio Facchetti

      Article first published online: 25 MAY 2011 | DOI: 10.1002/anie.201101640

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      All coordinated: Coordination polymers are an intriguing class of materials that combines classical and modern metal-coordination chemistry with the often complex formation of large supramolecular structures (see picture). A recent example is the formation of coordination nanotubes, in which the nature of the azine ligand profoundly defines the structure of the resulting assemblies.

  9. Minireview

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

      Selective Reduction of Carboxylic Acid Derivatives by Catalytic Hydrosilylation (pages 6004–6011)

      Dr. Daniele Addis, Shoubhik Das, Dr. Kathrin Junge and Prof. Dr. Matthias Beller

      Article first published online: 6 JUN 2011 | DOI: 10.1002/anie.201100145

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      Time for a change: Excellent chemoselectivity that is not attainable with traditional organometallic hydrides and hydrogenation catalysts is often observed in the catalytic hydrosilylation of carboxylic acid derivatives (see scheme). Moreover, hydrosilanes are easy-to-use reducing agents that can be activated under mild conditions. Until now, the potential of such reactions, which could be useful in complex organic synthesis, has been underestimated.

  10. Review

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

      Organocatalytic Enantioselective Acyl Transfer onto Racemic as well as meso Alcohols, Amines, and Thiols (pages 6012–6042)

      Dr. Christian E. Müller and Prof. Dr. Peter R. Schreiner

      Article first published online: 21 JUN 2011 | DOI: 10.1002/anie.201006128

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      Ode to the perfect pass: Acyl transfer is one of the most vibrant areas of organocatalysis. Such transfer reactions, in part mimicking nature, are steadily turning kinetic resolutions as well as enantioselective transformations into practical tools for the preparation of basic chiral building blocks.

  11. Communications

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

      Hopper-Like Single Crystals of Sodium Chloride Grown at the Interface of Metastable Water Droplets (pages 6044–6047)

      Jian Zhang, Dr. Shudong Zhang, Dr. Zhenyang Wang, Prof. Dr. Zhongping Zhang, Shuangshuang Wang and Prof. Dr. Suhua Wang

      Article first published online: 13 MAY 2011 | DOI: 10.1002/anie.201101704

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      Plain cubes are passé: Hopper-like single crystals of NaCl and KCl are successfully formed at the interface of metastable water microdroplets; these crystals then self-assemble (see picture). The growth mechanism and method for controlling the crystallization of the water-soluble species are proposed.

    2. Penrose Stairs

      Illusory Molecular Expression of “Penrose Stairs” by an Aromatic Hydrocarbon (pages 6048–6051)

      Dr. Waka Nakanishi, Taisuke Matsuno, Prof. Dr. Junji Ichikawa and Prof. Dr. Hiroyuki Isobe

      Article first published online: 23 MAY 2011 | DOI: 10.1002/anie.201102210

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      Ascending and Descending: A combination of two helical molecules and two twisting covalent axes in the form of a macrocycle conjures an illusory molecular object that has a seemingly impossible molecular structure, that is, an endlessly descending circle that consists of an sp2-carbon network, which can be regarded as the molecular expression of Penrose stairs (see picture).

    3. Nanoparticles

      Mixing an Aqueous Suspension of Pd or Au Nanocrystals with a Less Polar Solvent Can Cause Changes to Size, Morphology, or Both (pages 6052–6055)

      Dr. Byungkwon Lim, Dr. Taekyung Yu, Jinho Park, Yiqun Zheng and Prof. Younan Xia

      Article first published online: 5 MAY 2011 | DOI: 10.1002/anie.201101666

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      Easy control: Small Pd and Au nanocrystals exhibited a drastic change in size and/or morphology when their aqueous suspensions were mixed with a solvent (e.g., acetone or tetrahydrofuran) less polar than water. The morphological changes occurred through particle coalescence, which was triggered by the abrupt reduction in colloidal stability upon partial solvent exchange.

    4. Cross-Coupling

      Nickel-Catalyzed Cross-Coupling of Styrenyl Epoxides with Boronic Acids (pages 6056–6059)

      Daniel K. Nielsen and Prof. Abigail G. Doyle

      Article first published online: 13 MAY 2011 | DOI: 10.1002/anie.201101191

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      Let's get multicatalytic! A Ni0 catalyst complexed with a biaryldialkyl monophosphine ligand facilitates C[BOND]C bond formation between styrenyl epoxides and aryl boronic acids (see scheme). X-ray analysis of a catalytically active nickel/ligand complex supports a redox pathway involving Cmath image[BOND]O bond activation. A variety of α-substituted alcohols were generated with good reaction efficiency by a multicatalytic sequence.

    5. Fullerenes

      Hierarchical Selectivity in Fullerenes: Site-, Regio-, Diastereo-, and Enantiocontrol of the 1,3-Dipolar Cycloaddition to C70 (pages 6060–6064)

      Enrique E. Maroto, Dr. Abel de Cózar, Dr. Salvatore Filippone, Dr. Ángel Martín-Domenech, Prof. Dr. Margarita Suarez, Prof. Dr. Fernando P. Cossío and Prof. Dr. Nazario Martín

      Article first published online: 9 MAY 2011 | DOI: 10.1002/anie.201101246

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      Make your choice of stereochemistry: The first enantioselective cycloaddition of N-metalated azomethine ylides to the C70 molecule affords both pyrrolidino[70]fullerene enantiomers, with ee values over 90 %, depending on the chiral metal complex used (see picture). The high site- and regioselectivity observed has been accounted for by the nucleophilic and electrophilic Fukui indexes determined by theoretical calculations.

    6. Nanomaterials

      Ultrasmall Color-Tunable Copper-Doped Ternary Semiconductor Nanocrystal Emitters (pages 6065–6069)

      Suresh Sarkar, Niladri S. Karan and Narayan Pradhan

      Article first published online: 13 MAY 2011 | DOI: 10.1002/anie.201101572

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      Surface cation exchange of ZnII for InIII allows the emission of Cu-doped zinc indium selenide semiconductor nanocrystals to be tuned in the range of 660–540 nm, and thus the emission color to be varied from red to green (see picture; the arrow indicates increasing ZnII content).

    7. Protein Nanofibrils

      Photoelectric Protein Nanofibrils of α-Synuclein with Embedded Iron and Phthalocyanine Tetrasulfonate (pages 6070–6074)

      Yeon Sun Choi, Jehoon Kim, Ghibom Bhak, Dr. Daekyun Lee and Prof. Seung R. Paik

      Article first published online: 20 MAY 2011 | DOI: 10.1002/anie.201006859

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      Daylight saving: Hybrid protein nanofibrils were prepared by phthalocyanine tetrasulfonate (PcTS)-mediated unit assembly of iron-induced α-synuclein oligomers (see picture). The nanofibrils, which can be tightly packed into a 2D array, show the photoelectric properties of light harvesting and electrical conductivity.

    8. Enzyme Assays

      Profiling of Active Thrombin in Human Blood by Supramolecular Complexes (pages 6075–6078)

      Dr. Jens Müller, Tobias Becher, Jennifer Braunstein, Dr. Philipp Berdel, Dr. Sascha Gravius, Falk Rohrbach, Prof. Dr. Johannes Oldenburg, Prof. Dr. Günter Mayer and Prof. Dr. Bernd Pötzsch

      Article first published online: 17 MAY 2011 | DOI: 10.1002/anie.201007032

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      To clot or not to clot: The coagulation system is a multienzymatic network associated with bleeding or thrombosis in patients. A supramolecular oligonucleotide-adapted approach (see picture) makes thrombin, the key enzyme of this network, measurable in vivo. In patients undergoing hip-replacement surgery, thrombin was identified as a valuable biomarker to allow monitoring of the activity level of the coagulation system under clinical conditions.

    9. Heterodimers

      Quantum Dot–Bridge–Fullerene Heterodimers with Controlled Photoinduced Electron Transfer (pages 6079–6083)

      Dr. Zhihua Xu and Dr. Mircea Cotlet

      Article first published online: 10 MAY 2011 | DOI: 10.1002/anie.201007270

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      Link and gain: A series of donor–bridge–acceptor systems in the form of core/shell CdSe/ZnS quantum dot–bridge–fullerene heterodimers (see picture) with varying bridge length and varying quantum dot size were self-assembled by a surface-based stepwise method to demonstrate control of the rate and of the magnitude of fluctuations of photoinduced electron transfer at the single-molecule level.

    10. Carbohydrate Binding

      Solid-State NMR Spectroscopic Analysis of the Ca2+-Dependent Mannose Binding of Pradimicin A (pages 6084–6088)

      Dr. Yu Nakagawa, Dr. Yuichi Masuda, Keita Yamada, Takashi Doi, Prof. K. Takegoshi, Prof. Yasuhiro Igarashi and Dr. Yukishige Ito

      Article first published online: 19 MAY 2011 | DOI: 10.1002/anie.201007775

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      Aggregation facilitates analysis: The Ca2+-dependent mannose (Man) binding of the nonpeptidic carbohydrate binder pradimicin A (PRM-A) was investigated in the solid state. The use of PRM-A aggregates eliminated problems associated with the three-component equilibrium. A combination of 113Cd NMR spectroscopy and 2D dipolar-assisted rotational resonance revealed the mannose-binding site of PRM-A and the crucial role of the Ca2+ ion (see binding model).

    11. SERS Reporters

      Ultrasensitive Near-Infrared Raman Reporters for SERS-Based In Vivo Cancer Detection (pages 6089–6092)

      Animesh Samanta, Dr. Kaustabh Kumar Maiti, Kiat-Seng Soh, Xiaojun Liao, Dr. Marc Vendrell, Dr. U. S. Dinish, Dr. Seong-Wook Yun, Ramaswamy Bhuvaneswari, Hyori Kim, Shashi Rautela, Prof. Junho Chung, Prof. Malini Olivo and Prof. Young-Tae Chang

      Article first published online: 17 MAY 2011 | DOI: 10.1002/anie.201007841

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      Of good report: Synthesis and screening of an 80-member tricarbocyanine library identified CyNAMLA-381 as a near-IR surface-enhanced Raman spectroscopy (SERS) reporter with good signal stability and higher sensitivity than the standard. Encapsulation of CyNAMLA-381 on gold nanoparticles and conjugation to an antibody afforded SERS nanotags with excellent sensitivity, stability, and tumor specificity in xenograft models (see picture).

    12. Cell Imaging

      Long-Term Real-Time Tracking of Lanthanide Ion Doped Upconverting Nanoparticles in Living Cells (pages 6093–6097)

      Dr. Sang Hwan Nam, Yun Mi Bae, Yong Il Park, Dr. Jeong Hyun Kim, Dr. Hyung Min Kim, Prof. Dr. Joon Sig Choi, Dr. Kang Taek Lee, Prof. Dr. Taeghwan Hyeon and Dr. Yung Doug Suh

      Article first published online: 13 MAY 2011 | DOI: 10.1002/anie.201007979

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      A track record: Upconverting nanoparticles (UCNPs) were tracked in living HeLa cells and their active transport by motor proteins was visualized in real time. The remarkable photostability of the UCNPs and the noninvasiveness of near-infrared excitation allowed continuous observation of living cells for as long as 6 h.

    13. Drug Delivery

      Self-Assembly of a Bifunctional DNA Carrier for Drug Delivery (pages 6098–6101)

      Dr. Kelong Wang, Mingxu You, Dr. Yan Chen, Da Han, Zhi Zhu, Jin Huang, Dr. Kathryn Williams, Prof. Chaoyong James Yang and Prof. Dr. Weihong Tan

      Article first published online: 18 MAY 2011 | DOI: 10.1002/anie.201008053

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      Speedy delivery: A self-assembled bifunctional unit incorporates a DNA aptamer for target recognition (see picture, green helix) and a G-quadruplex for drug loading. The modified DNA selectively delivered a photosensitizer (red bars) to cancer cells; irradiation with visible light generated high toxicity.

    14. Smart Materials

      Manipulating Sticky and Non-Sticky Properties in a Single Material (pages 6102–6104)

      Zhiqiang Cao, Norman Brault, Hong Xue, Andrew Keefe and Prof. Shaoyi Jiang

      Article first published online: 23 MAY 2011 | DOI: 10.1002/anie.201100004

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      Sticky and non-sticky, together? A newly developed zwitterionic material (CB-OH; blue structure in scheme) has an equilibrium counterpart (CB-Ring; red). This interchangeable material allows control over two distinct properties: “non-sticky” CB-OH (biomolecular resistance) and “sticky” CB-Ring (binding by covalent bonds).

    15. Porous Coordination Networks

      Ab Initio Powder Diffraction Structure Analysis of a Host–Guest Network: Short Contacts between Tetrathiafulvalene Molecules in a Pore (pages 6105–6108)

      Dr. Javier Martí-Rujas , Dr. Nazrul Islam, Dr. Daisuke Hashizume, Dr. Fujio Izumi, Prof. Dr. Makoto Fujita, Hyun Jae Song, Prof. Dr. Hee Cheul Choi and Prof. Dr. Masaki Kawano

      Article first published online: 19 MAY 2011 | DOI: 10.1002/anie.201100176

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      Synchrotron powder XRD analysis was used to solve the crystal structure of a kinetically controlled coordination network including tetrathiafulvalene (TTF) guests, which has a large unit cell (15 729(1) Å3). Very short S⋅⋅⋅S contacts among the TTF guests were achieved by confinement in the network pores (see picture).

    16. Functional Nanoparticles

      Tunable, Ultrasensitive pH-Responsive Nanoparticles Targeting Specific Endocytic Organelles in Living Cells (pages 6109–6114)

      Dr. Kejin Zhou, Dr. Yiguang Wang, Dr. Xiaonan Huang, Prof. Katherine Luby-Phelps, Prof. Baran D. Sumer and Prof. Jinming Gao

      Article first published online: 14 APR 2011 | DOI: 10.1002/anie.201100884

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      Switch it up: Tunable, pH-responsive nanoparticles can be selectively activated in different endocytic compartments. At high pH values, micelle formation (see picture, left) quenches fluorescence by Förster resonance energy transfer. The micelles disassemble at low pH values, leading to fluorescence emission. This nonlinear on/off nanoplatform offers many exciting opportunities in diagnostic imaging and drug-delivery applications.

    17. Biomimicry

      Bioinspired Functionalization of Silica-Encapsulated Yeast Cells (pages 6115–6118)

      Dr. Sung Ho Yang, Eun Hyea Ko, Prof. Dr. Young Hwan Jung and Prof. Dr. Insung S. Choi

      Article first published online: 30 MAY 2011 | DOI: 10.1002/anie.201102030

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      Tough shell: Living yeast cells can be simultaneously silica-encapsulated and thiol-functionalized by polycondensation of silicic acid and (3-mercaptopropyl)trimethoxysilane under mild conditions. Various functions such as fluorescent dyes (see picture; green: fluorescein, red: rhodamine), chemical moieties, or proteins, can be introduced to the artificial shell by using maleimide-based coupling reactions.

    18. Photoredox Catalysis

      Photoredox Catalysis: A Mild, Operationally Simple Approach to the Synthesis of α-Trifluoromethyl Carbonyl Compounds (pages 6119–6122)

      Phong V. Pham, David A. Nagib and Prof. David W. C. MacMillan

      Article first published online: 23 MAY 2011 | DOI: 10.1002/anie.201101861

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      A facile and efficient method for the α-trifluoromethylation of carbonyl compounds and enolsilanes has been accomplished through application of a photoredox catalysis strategy. A one-flask procedure for the direct α-trifluoromethylation and α-perfluoroalkylation of ketone, amide, and ester substrates as well as silylketene acetals is described (see scheme).

      Corrected by:

      Corrigendum: Corrigendum: Photoredox Catalysis: A Mild, Operationally Simple Approach to the Synthesis of α-Trifluoromethyl Carbonyl Compounds

      Vol. 50, Issue 40, 9232, Article first published online: 21 SEP 2011

    19. Organocatalysis

      Dual Hydrogen-Bond/Enamine Catalysis Enables a Direct Enantioselective Three-Component Domino Reaction (pages 6123–6127)

      Dr. Hasibur Rahaman, Dr. Ádám Madarász, Dr. Imre Pápai and Prof. Dr. Petri M. Pihko

      Article first published online: 23 MAY 2011 | DOI: 10.1002/anie.201101835

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      It takes two to tango: A dual catalyst system, composed of a highly enantioselective enamine catalyst and a multiple-hydrogen-bond catalyst, enabled the chemoselective union of two aldehydes and a nitromethane unit with near-perfect enantioselectivities, excellent diastereoselectivities, and high yields under neutral conditions (see scheme).

    20. Palladium Catalysis

      Palladium-Catalyzed Elimination/Isomerization of Enol Triflates into 1,3-Dienes (pages 6128–6132)

      Ian T. Crouch, Timothy Dreier and Prof. Doug E. Frantz

      Article first published online: 13 MAY 2011 | DOI: 10.1002/anie.201101820

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      Dying to be Dienes: Substituted 1,3-dienes were synthesized by the title reaction (see scheme; Tf=trifluoromethanesulfonyl). Preliminary studies support a mechanistically distinct pathway that involves an initial β-hydride elimination from a cationic vinyl palladium(II) intermediate, a subsequent regiospecific hydropalladation of the corresponding allene intermediate, and a final β-hydride elimination.

    21. Homing Peptides

      Screening of a Combinatorial Homing Peptide Library for Selective Cellular Delivery (pages 6133–6136)

      Dr. Nina Svensen, Dr. Juan José Díaz-Mochón, Dr. Kevin Dhaliwal, Songsak Planonth, Dr. Michael Dewar, Dr. J. Douglas Armstrong and Prof. Mark Bradley

      Article first published online: 17 MAY 2011 | DOI: 10.1002/anie.201101804

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      To the point: The identification of peptides to optimize both the delivery and tumor penetration of existing cancer drugs in a cell-selective manner would be highly desirable. The screening of a peptide nucleic acid (PNA)-encoded peptide library (see picture) now allows the identification of versatile cell homing peptides for any cell type of interest.

    22. Protein Synthesis

      Total Chemical Synthesis of a 304 Amino Acid K48-Linked Tetraubiquitin Protein (pages 6137–6141)

      Dr. K. S. Ajish Kumar, Dr. Sudhir N. Bavikar, Liat Spasser, Tal Moyal, Shimrit Ohayon and Prof. Ashraf Brik

      Article first published online: 18 MAY 2011 | DOI: 10.1002/anie.201101920

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      A new record: The largest chemically synthesized polypeptide composed of 304 residues, which corresponds to folded K48-tetraubiquitin, has been achieved (see scheme). The presented synthetic method could be applied to any of the remaining tetraubiquitin chains, and should ultimately assist ongoing efforts to unravel how the remarkable diversity of ubiquitin signaling is achieved.

    23. Biaryls

      Coupling of Quinone Monoacetals Promoted by Sandwiched Brønsted Acids: Synthesis of Oxygenated Biaryls (pages 6142–6146)

      Dr. Toshifumi Dohi, Naohiko Washimi, Tohru Kamitanaka, Kei-ichiro Fukushima and Prof. Dr. Yasuyuki Kita

      Article first published online: 23 MAY 2011 | DOI: 10.1002/anie.201101646

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      Unusual protons: Brønsted acids sandwiched between sheets of solid acids, such as montmorillonites, activated quinone monoacetals 1 to selectively react with aromatic nucleophiles 2 in an unprecedented substitution reaction. The synthetic utility of the strategy for obtaining highly oxygenated biaryls 3 is highlighted by the synthesis of gilvocarcin aglycones.

    24. Peptide Mimics

      Self-Activation in De Novo Designed Mimics of Cell-Penetrating Peptides (pages 6147–6150)

      Dr. Abhigyan Som, A. Ozgul Tezgel, Dr. Gregory J. Gabriel and Prof. Gregory N. Tew

      Article first published online: 17 MAY 2011 | DOI: 10.1002/anie.201101535

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      DIY transduction: Cell-penetrating peptides (CPPs) efficiently cross the nonpolar biological membrane, but activation by hydrophobic counterions is essential for transport activity. Polymeric mimics of CPPs are coupled with hydrophobic side chains; the “self-activation” in these species is demonstrated by transport of the fluorescent probe CF out of bilayer vesicles.

    25. Drug Interactions

      Soluble Synthetic Analogues of Malaria Pigment: Structure of Mesohematin Anhydride and its Interaction with Chloroquine in Solution (pages 6151–6154)

      Prof.  D. Scott Bohle, Erin L. Dodd, Aaron J. Kosar, Lauren Sharma, Peter W. Stephens, Liliana Suárez and Dagobert Tazoo

      Article first published online: 3 MAY 2011 | DOI: 10.1002/anie.201100910

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      Where the action is: Changing the vinyl groups of hematin anhydride to either ethyl or hydrogen groups results in increased solubility (see picture; Por=porphyrin). Determination of the weak binding constants of the antimalarial drug chloroquine to dimers of these hematin anhydride analogues suggests that solution-phase heme/drug interactions alone are unlikely to be the origin of the action of the drug.

    26. Synthetic Methods

      Palladium-Catalyzed Oxidative Borylative Carbocyclization of Enallenes (pages 6155–6159)

      Andreas K. Å. Persson, Tuo Jiang, Magnus T. Johnson and Prof. Jan-E. Bäckvall

      Article first published online: 17 MAY 2011 | DOI: 10.1002/anie.201008032

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      An efficient oxidative carbocyclization/borylation of enallenes uses Pd(OAc)2 as the catalyst, B2pin2 as the boron-transfer reagent, and 1,4-benzoquinone (BQ) as the oxidant (see scheme). The reaction seems to take place through activation of the allene by a PdII complex to give an alkenyl–PdII intermediate followed by carbopalladation of the olefin and subsequent cleavage of the intermediate palladium–carbon bond by the boron reagent.

    27. Bioorganic Chemistry

      A Microbiological–Chemical Strategy to Produce Chondroitin Sulfate A,C (pages 6160–6163)

      Dr. Emiliano Bedini, Dr. Cristina De Castro, Prof. Mario De Rosa, Annalida Di Nola, Dr. Alfonso Iadonisi, Dr. Odile F. Restaino, Prof. Chiara Schiraldi and Prof. Michelangelo Parrilli

      Article first published online: 18 MAY 2011 | DOI: 10.1002/anie.201101142

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      No pigs, no cows needed: Chondroitin sulfate for pharmacological uses is obtained from animal sources in low abundance and with a laborious downstream purification. It has now been synthesized for the first time by an innovative microbiological–chemical approach consisting of chondroitin production from E. coli K4 fed-batch fermentation and its subsequent regioselective sulfation in five steps and 61 % overall yield (see scheme).

    28. Natural Products

      Total Synthesis of (−)-Isatisine A (pages 6164–6166)

      Xiao Zhang, Tong Mu, Fuxu Zhan, Lijuan Ma and Prof. Guangxin Liang

      Article first published online: 23 MAY 2011 | DOI: 10.1002/anie.201101621

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      Short and sweet: (−)-Isatisine A was constructed using common and inexpensive building blocks, such as indole and D-ribose (see scheme). The synthesis features an unprecedented intramolecular C glycosylation of an indole and an oxidative ring contraction.

    29. Asymmetric Synthesis

      Palladium-Catalyzed Diastereo- and Enantioselective Synthesis of Substituted Cyclopentanes through a Dynamic Kinetic Asymmetric Formal [3+2]-Cycloaddition of Vinyl Cyclopropanes and Alkylidene Azlactones (pages 6167–6170)

      Prof. Barry M. Trost and Patrick J. Morris

      Article first published online: 23 MAY 2011 | DOI: 10.1002/anie.201101684

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      An enantioselective preparation of vinylcyclopentanes has been achieved through the title reaction (see scheme). A range of aryl, heterocyclic, alkenyl, and alkyl substituted azlactone alkylidenes have been utilized, giving the cyclopentane products in good yield, diastereomeric ratio, and enantioselectivity.

    30. Nitrogen Heterocycles

      Synthesis with Perfect Atom Economy: Generation of Diazo Ketones by 1,3-Dipolar Cycloaddition of Nitrous Oxide at Cyclic Alkynes under Mild Conditions (pages 6171–6174)

      Prof. Dr. Klaus Banert and Oliver Plefka

      Article first published online: 25 MAY 2011 | DOI: 10.1002/anie.201101326

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      A cascade of five steps, transforms cyclooctynes in the presence of nucleophiles NuH and nitrous oxide, into the depicted products (see scheme). In another example, nitrous oxide was added at a cycloalkyne at −25 °C to generate the corresponding diazo ketone. In both cases, all three atoms of nitrous oxide were incorporated into the products.

    31. Protecting Groups

      Chelating Carboxylic Acid Amides as Robust Relay Protecting Groups of Carboxylic Acids and their Cleavage under Mild Conditions (pages 6175–6177)

      Dipl.-Chem. Manuel C. Bröhmer, Stephan Mundinger, Prof. Dr. Stefan Bräse and Prof. Dr. Willi Bannwarth

      Article first published online: 30 MAY 2011 | DOI: 10.1002/anie.201100271

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      Free choice: Carboxamides of bispicolylamine are alternative protecting groups for carboxylic acids (see scheme). As a consequence of their straightforward applicability, their high chemical stability towards a broad range of conditions, and their selective cleavage under mild conditions to give either carboxylic acids or their methyl esters, this new protection method should find widespread application in the realm of organic synthesis.

    32. Metastable Metals

      A Metastable Metal with Decagonal Local Symmetry Obtained by Low-Temperature Pseudomorphosis (pages 6178–6180)

      Martin Kaiser, Dr. Anna Isaeva and Prof. Dr. Michael Ruck

      Article first published online: 17 MAY 2011 | DOI: 10.1002/anie.201101248

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      Losing an I: The metastable metallic compound Bi28Ni25 is the product of the mild reduction of the solid precursor Bi28Ni25I5. In a pseudomorphosis the iodine is completely extracted while the macroscopic crystals are preserved. The unique structure is composed of decagonal nanorods, which consist of an outer Bi tube, an inner Ni tube, and additional Bi atoms along the central axis (see structure).

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      Preview: Angew. Chem. Int. Ed. 28/2011 (page 6181)

      Article first published online: 21 JUN 2011 | DOI: 10.1002/anie.201190054

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