Angewandte Chemie International Edition

Cover image for Vol. 50 Issue 16

April 11, 2011

Volume 50, Issue 16

Pages 3575–3816

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Correspondence
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    15. Back Cover
    1. Cover Picture: Enantioselective Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters: Methodology and Applications (Angew. Chem. Int. Ed. 16/2011) (page 3575)

      Dr. Ravindra P. Sonawane, Dr. Vishal Jheengut, Dr. Constantinos Rabalakos, Dr. Robin Larouche-Gauthier, Helen K. Scott and Prof. Varinder K. Aggarwal

      Version of Record online: 18 MAR 2011 | DOI: 10.1002/anie.201101504

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      The combination of two reactions lithiation/borylation and subsequent one-carbon homologation or vinylation to deliver functionalized compounds having quaternary centers in very high enantioselectivity is described by V. Aggarwal et al. in their Communication on page 3760 ff. Bristol's International Balloon Festival and the Clifton suspension bridge act as the backdrop of this chemistry.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Correspondence
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    15. Back Cover
    1. Inside Cover: Crystalline Lipid Domains: Characterization by X-Ray Diffraction and their Relation to Biology (Angew. Chem. Int. Ed. 16/2011) (page 3576)

      Roy Ziblat, Prof. Leslie Leiserowitz and Prof. Lia Addadi

      Version of Record online: 4 MAR 2011 | DOI: 10.1002/anie.201101208

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      Saturated lipid molecules may spontaneously form crystalline lipid domains. X-ray diffraction studies performed on artificial lipid vesicles, monolayers, and supported bilayers have provided substantial information on the lipid organization in these domains. In their Minireview on page 3620 ff., R. Ziblat, L. Leiserowitz, and L. Addadi discuss various X-ray methods and the derived structural motifs of the crystalline lipid domains.

  3. Graphical Abstract

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

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Correspondence
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    15. Back Cover
    1. Anthony K. Cheetham (pages 3596–3598)

      Version of Record online: 25 MAR 2011 | DOI: 10.1002/anie.201100130

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      “My favorite subject at school was chemistry, though I was not particularly good at it at the time! My greatest achievement has been mentoring a large number of very successful young scientists …” This and more about Anthony K. Cheetham can be found on page 3598.

  6. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Correspondence
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    15. Back Cover
    1. Modern Drug Synthesis. Edited by Jie Jack Li and Douglas S. Johnson. (page 3600)

      Philippe Dauban

      Version of Record online: 29 MAR 2011 | DOI: 10.1002/anie.201101165

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      John Wiley & Sons, Hoboken 2010. 356 pp., hardcover, € 95.90.—ISBN 978-0470525838

  8. Highlights

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

      Photothermal Contrast Reaches Single-Molecule Sensitivity (pages 3602–3604)

      Prof. Dr. Thomas Basché

      Version of Record online: 4 MAR 2011 | DOI: 10.1002/anie.201100401

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      The detection of single-molecule absorption under ambient conditions is a very challenging task, because the tiny change in transmission is difficult to discriminate against the noise from the light beam and from scattering. By pushing the detection limits of photothermal contrast imaging, single-molecule absorption has been measured by the refraction index change induced in the environment by the heat released from the molecule (see image).

    2. One-Pot Reactions

      One-Pot Reactions Accelerate the Synthesis of Active Pharmaceutical Ingredients (pages 3605–3607)

      Dr. Carine Vaxelaire, Philipp Winter and Prof. Mathias Christmann

      Version of Record online: 4 MAR 2011 | DOI: 10.1002/anie.201100059

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      All in one: A one-pot synthesis of the dipeptidylpeptidase IV selective inhibitor ABT-341 (see structure) by using an “uninterrupted sequence of reactions” has been developed. This strategy broadens the spectrum of one-pot reactions and is poised to speed up the synthesis of medicinally relevant drug compounds.

  9. Correspondence

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

      Limitations of the s(E+N) and Related Equations: Solvent Dependence of Electrophilicity (pages 3608–3611)

      Dr. T. William Bentley

      Version of Record online: 9 MAR 2011 | DOI: 10.1002/anie.201005816

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      Solvent matters: Cations are reference substrates in the equation log k=s(E+N); neglect of solvent effects (see picture; TS=transition state) on their electrophilicity (E) leads to unreliable values of the nucleophilicity (N) and slope (s) parameters that characterize nucleophiles (k is the rate constant). Consequently, these parameters are not recommended for a general scale of nucleophilicity as suggested by Mayr and co-workers.

    2. Reply to T. W. Bentley: Limitations of the s(E+N) and Related Equations (pages 3612–3618)

      Prof. Dr. Herbert Mayr

      Version of Record online: 17 MAR 2011 | DOI: 10.1002/anie.201007923

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      Simple and unambiguous: In the equation log k=s(E+N), the nucleophilicity N is obtained through the intercepts on the abscissa of linear log k versus E (electrophilicity) correlations. This approach places nucleophiles that differ by more than 30 orders of magnitude in reactivity on a single scale that can be used as a guide for designing organic syntheses. The equation in question is not only more practical but is also more precise than Bentley's alternatives.

  10. Minireview

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

      Crystalline Lipid Domains: Characterization by X-Ray Diffraction and their Relation to Biology (pages 3620–3629)

      Roy Ziblat, Prof. Leslie Leiserowitz and Prof. Lia Addadi

      Version of Record online: 25 FEB 2011 | DOI: 10.1002/anie.201004470

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      Are we all on the same raft? Membrane lipids segregate into domains. During the past two decades the structural organization of such lipid domains has been studied by several X-ray diffraction techniques. The correlation between crystalline lipid domains and lipid phases, and their relevance to functional domains in biological membranes are discussed in this Minireview.

  11. Review

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

      Zintl Ions, Cage Compounds, and Intermetalloid Clusters of Group 14 and Group 15 Elements (pages 3630–3670)

      Dr. Sandra Scharfe, Dr. Florian Kraus, Saskia Stegmaier, Dr. Annette Schier and Prof. Dr. Thomas F. Fässler

      Version of Record online: 31 MAR 2011 | DOI: 10.1002/anie.201001630

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      Zintl ions go intermetalloid: Zintl phases are mainly at home in solid-state chemistry, but their soluble representatives open fascinating possibilities as precursors for intermetalloid clusters and cage compounds. The recent upsurge of research activity in this field has now provided a rich plethora of new compounds, for example Zintl ions functionalized with organic groups, by oxidative coupling reactions, or by encapsulation of metal ions with the formation of endohedral clusters and intermetalloid compounds.

  12. Communications

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

      Enantioselective Total Synthesis of (−)-Jiadifenolide (pages 3672–3676)

      Dr. Jing Xu, Lynnie Trzoss, Weng K. Chang and Prof. Dr. Emmanuel A. Theodorakis

      Version of Record online: 11 MAR 2011 | DOI: 10.1002/anie.201100313

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      Neurofunk: Highlights of the synthesis of 1, a potent modulator of neurotrophic factors, include construction of the B ring through an asymmetric Robinson annulation, assembly of the E ring lactone through a novel acid-induced cascade reaction, and Pd0-mediated carbomethoxylation and methylation reactions for the construction of the C and A rings, respectively.

    2. Synthetic Methods

      One-Step Catalytic Asymmetric Synthesis of Configurationally Stable Tröger Bases (pages 3677–3680)

      Ankit Sharma, Dr. Laure Guénée, Dr. Jean-Valère Naubron and Prof. Jérôme Lacour

      Version of Record online: 18 MAR 2011 | DOI: 10.1002/anie.201100134

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      Bridging the gap: Configurationally stable ethano-bridged Tröger bases have been prepared in a single step by the direct rhodium(II)-catalyzed reaction of methano-bridged Tröger bases and diazo esters (see scheme). The process is general, enantiospecific, diastereoselective (with introduction of a new quaternary carbon center), and regioselective.

    3. Supramolecular Catalysis

      Controlled Assembly of Chiral Tetraaminophosphonium Aryloxide–Arylhydroxide(s) in Solution (pages 3681–3683)

      Dr. Daisuke Uraguchi, Yusuke Ueki and Prof. Dr. Takashi Ooi

      Version of Record online: 16 MAR 2011 | DOI: 10.1002/anie.201007752

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      As you like it: Low-temperature 31P NMR spectroscopic and X-ray crystallographic analyses have revealed that chiral P-spiro triaminoiminophosphorane 1 and 3,5-dichlorophenol (2) selectively assemble into three types of discrete molecular structures, 1⋅[2]n (n=1–3; see picture) depending on the stoichiometry of 2.

    4. Self-Assembly

      Hierarchical Assembly of a Phthalhydrazide-Functionalized Helicene (pages 3684–3687)

      Takahiro Kaseyama, Dr. Seiichi Furumi, Dr. Xuan Zhang, Prof. Ken Tanaka and Prof. Masayuki Takeuchi

      Version of Record online: 17 MAR 2011 | DOI: 10.1002/anie.201007849

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      High in fiber: 1D fibrous superstructures are formed by an enantiopure phthalhydrazide-functionalized helicene in nonpolar solvents. Trimeric disks are formed by hydrogen-bonding interactions of phthalhydrazide units that are longitudinally interlocked for optimal packing (see picture). The resulting supramolecular assemblies exhibited large circularly polarized luminescence in solution.

    5. Natural Product Synthesis

      A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide D (pages 3688–3691)

      Hosea M. Nelson, Kei Murakami, Dr. Scott C. Virgil and Prof. Dr. Brian M. Stoltz

      Version of Record online: 25 MAR 2011 | DOI: 10.1002/anie.201008003

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      In a flash: The total synthesis of transtaganolide and basiliolide natural products is achieved in three steps from achiral, monocyclic esters (see scheme). Featured in the syntheses are an Ireland-Claisen/Diels–Alder cascade and a novel methoxyacetylide coupling/cyclization sequence.

    6. Molecular Coolers

      Large Magnetocaloric Effect in a Wells–Dawson Type {Ni6Gd6P6} Cage (pages 3692–3695)

      Dr. Yan-Zhen Zheng, Dr. Marco Evangelisti and Prof. Dr. Richard E. P. Winpenny

      Version of Record online: 25 MAR 2011 | DOI: 10.1002/anie.201008074

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      Cool stuff: The usage of phosphonates has led to formation of a family of 3d–4f heterometallic cages with a Wells–Dawson-like structure (see picture; Gd, Dy, or Y purple; Ni cyan; P green; O orange; C gray). Magnetic studies show ferromagnetic interactions within the oxo-centered nickel triangle and huge entropy change in the Gd analogue, which, in principle, can be used as an ultralow-temperature coolant.

    7. Functional Coordination Polymers

      Phosphorescent Nanoscale Coordination Polymers as Contrast Agents for Optical Imaging (pages 3696–3700)

      Demin Liu, Rachel C. Huxford and Prof. Wenbin Lin

      Version of Record online: 17 MAR 2011 | DOI: 10.1002/anie.201008277

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      Seeing is believing: Phosphorescent nanoscale coordination polymers (NCPs) with unprecedentedly high dye loadings were coated with thin silica shells to tune the dye release kinetics (see picture). Further functionalization of the NCP/silica particles with poly(ethylene glycol) (PEG) and PEG-anisamide enhanced their biocompatibility and targeting ability, allowing cancer-specific imaging of human lung cancer H460 cells.

    8. Boron Nitride Monolayers

      Formation of Boron-Based Films and Boron Nitride Layers by CVD of a Boron Ester (pages 3701–3705)

      Priv.-Doz. Dr. Hermann Sachdev, Dr. Frank Müller and Prof. Dr. Stefan Hüfner

      Version of Record online: 18 MAR 2011 | DOI: 10.1002/anie.201003012

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      Directing films: The chemical vapor deposition of (MeO)3B on a multilayered Rh(111) substrate results in selective precursor decomposition leading to a boride-type film. This film can be oxidized into a well-ordered boron nitride monolayer (see picture with model structure), thus opening up a new approach to BN systems.

    9. Fingerprint Recognition

      A Release-Induced Response for the Rapid Recognition of Latent Fingerprints and Formation of Inkjet-Printed Patterns (pages 3706–3709)

      Shengyang Yang, Dr. Cai-Feng Wang and Prof. Su Chen

      Version of Record online: 17 MAR 2011 | DOI: 10.1002/anie.201006537

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      Enter the dragon: An electrospun nanofiber mat is used to identify latent fingerprints on various surfaces within 30 seconds and produce inkjet-printed patterns. In contrast to classical approaches, the method is easy-to-operate, environmentally friendly, and has implications in other applied systems including chemical sensors, drug delivery, biological detection, and microreactors.

    10. Attomolar DNA Detection

      Label-Free Detection of Few Copies of DNA with Carbon Nanotube Impedance Biosensors (pages 3710–3714)

      Tetiana Kurkina, Dr. Alexis Vlandas, Dr. Ashraf Ahmad, Prof. Klaus Kern and Dr. Kannan Balasubramanian

      Version of Record online: 18 MAR 2011 | DOI: 10.1002/anie.201006806

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      Finding that needle in the haystack: A label-free on-chip detection strategy based on carbon nanotubes (see picture) was used to detect an oligonucleotide target sequence of which less than 2000 copies were present in a 30 μL sample droplet, without the need for PCR. Instead, sensitive low-noise impedance measurement coupled to field-effect detection enabled attomolar DNA detection in a heterogeneous environment.

    11. Peptide Self-Assembly

      Morphological Transformation between Nanofibers and Vesicles in a Controllable Bipyridine–Tripeptide Self-Assembly (pages 3715–3719)

      Damei Ke, Dr. Chuanlang Zhan, Prof. Dr. Alexander D. Q. Li and Prof. Dr. Jiannian Yao

      Version of Record online: 15 FEB 2011 | DOI: 10.1002/anie.201006897

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      Tuning structures: Stimulus-responsive peptide self-assembly requires a balance of conformational change and structural continuity of stable β sheets. In an amphiphilic bipyridine–tripeptide model, temperature, and ultrasound switch a reversible morphological transformation between vesicles and nanofibers (see picture) through the synergistic effects of terminal β-sheet-forming peptides, flexible linkers, and rotatable bipyridine groups.

    12. Organic–Inorganic Hybrid Materials

      Real-Time Observation of the Self-Assembly of Hybrid Polyoxometalates Using Mass Spectrometry (pages 3720–3724)

      Dr. Elizabeth F. Wilson, Dr. Haralampos N. Miras, Mali H. Rosnes and Prof. Leroy Cronin

      Version of Record online: 24 MAR 2011 | DOI: 10.1002/anie.201006938

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      Catching a glimpse: Electrospray ionization mass spectrometry (ESI-MS) allows monitoring of the real-time, “in-solution” formation of an organic–inorganic polyoxometalate hybrid system (see picture). This has provided insight into the rearrangement involved in the formation of the manganese-Anderson cluster coordinated with tris(hydroxymethyl)aminomethane ligands, through the rearrangement of the [α-Mo8O26]4− cluster in the presence of Mn(CH3CO2)3.

    13. Heterogeneous Catalysis

      Mesoporous Multicomponent Nanocomposite Colloidal Spheres: Ideal High-Temperature Stable Model Catalysts (pages 3725–3729)

      Chen Chen, Caiyun Nan, Dr. Dingsheng Wang, Qiao Su, Haohong Duan, Xiangwen Liu, Lesheng Zhang, Deren Chu, Prof. Weiguo Song, Dr. Qing Peng and Prof. Yadong Li

      Version of Record online: 21 MAR 2011 | DOI: 10.1002/anie.201007229

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      A caged catalyst: Noble-metal and oxide nanoparticles can be assembled to obtain high-temperature-stable mesoporous multicomponent nanocomposite colloidal spheres (MMNCSs; see picture). CO oxidation and cyclohexene hydroconversion were selected to examine the catalytic activity, selectivity, and thermal stability of these MMNCSs. The exhibited catalytic properties suggest that the reported MMNCSs are ideal model catalysts for high-temperature reactions.

    14. Natural Product Synthesis

      Synthesis of (−)-Viriditoxin: A 6,6′-Binaphthopyran-2-one that Targets the Bacterial Cell Division Protein FtsZ (pages 3730–3733)

      Dr. Young Sam Park, Charles I. Grove, Dr. Marcos González-López, Dr. Sameer Urgaonkar, Dr. James C. Fettinger and Prof. Jared T. Shaw

      Version of Record online: 16 MAR 2011 | DOI: 10.1002/anie.201007298

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      Remote control: Vanadium catalysts provide the key to synthesizing the bacteria-fighting natural product viriditoxin. An achiral catalyst shows modest levels of remote diastereocontrol induced by the lactone stereogenic center and chiral catalysts can be used to enhance or reverse this inherent selectivity.

    15. Nanoscale Tailoring

      Fine Characteristics Tailoring of Organic and Inorganic Nanowires Using Focused Electron-Beam Irradiation (pages 3734–3738)

      Dr. Young Ki Hong, Dr. Dong Hyuk Park, Seong Gi Jo, Min Ho Koo, Dae-Chul Kim, Prof. Jeongyong Kim, Joon-Sung Kim, Dr. Sung-Yeon Jang and Prof. Jinsoo Joo

      Version of Record online: 14 MAR 2011 | DOI: 10.1002/anie.201007358

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      Let your little light shine: Light-emitting organic poly(3-methylthiophene) (P3MT) and inorganic titanium dioxide single nanowires (NWs) treated with focused electron beams have multiple 1D serial compartments (see picture) similar to superlattice NWs, which are applicable to light-emitting color barcode NWs. The structural, optical, and electrical properties of the treated NW compartments can be controlled through the irradiation conditions.

    16. Microbubbles

      Tunable Synthesis of Encapsulated Microbubbles by Coupled Electrophoretic Stabilization and Electrochemical Inflation (pages 3739–3743)

      Yu-Wen Huang, Faisal A. Shaikh and Prof. Victor M. Ugaz

      Version of Record online: 25 MAR 2011 | DOI: 10.1002/anie.201007377

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      Visible to the naked eye: An interplay between microscale electrophoresis and electrochemistry was exploited to simultaneously confine macromolecular encapsulants near an electrode surface while inflating them with gases evolved from the electrochemical reactions localized there. The compacted film can be seen under ordinary white light even when samples are unlabeled thus enabling a label-free technique for the detection of a variety of macromolecules including DNA, proteins, and cyclodextrans.

    17. Homogeneous Catalysis

      cis/trans Isomerization of Phosphinesulfonate Palladium(II) Complexes (pages 3744–3746)

      Dr. Matthew P. Conley and Prof. Dr. Richard F. Jordan

      Version of Record online: 16 MAR 2011 | DOI: 10.1002/anie.201100065

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      With a little help from a friend: Chain growth in olefin polymerization by [{PO}PdR] catalysts is believed to occur by unimolecular cis-P,R- to trans-P,R-[{PO}PdR(olefin)] isomerization, with subsequent insertion. Studies with [{PO}Pd(py)2]+ (py=pyridine) and non-equilibrium cis/trans mixtures of [{PO}PdClP(O-o-tolyl)3] indicate that an external ligand is necessary for cis/trans isomerization of {PO}Pd complexes (see scheme). {PO}=2-Phosphinosulfonate.

    18. Magnetic Nanomaterials

      Magnetically Responsive Photonic Nanochains (pages 3747–3750)

      Yongxing Hu, Le He and Prof. Yadong Yin

      Version of Record online: 14 MAR 2011 | DOI: 10.1002/anie.201100290

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      Nano-peapods: Magnetically responsive photonic nanochains have been produced by inducing chain alignment of uniform magnetic particles during their silica coating process and then allowing additional deposited silica to wrap entire structures. The optical diffraction of these nanochains can be switched on and off by applying magnetic fields.

    19. Biosensors

      Fluorogenic DNAzyme Probes as Bacterial Indicators (pages 3751–3754)

      Dr. M. Monsur Ali, Sergio D. Aguirre, Dr. Hadeer Lazim and Prof. Dr. Yingfu Li

      Version of Record online: 15 MAR 2011 | DOI: 10.1002/anie.201100477

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      Lighting up bacteria: An RNA-cleaving fluorescent DNAzyme (RFD) can produce a fluorescent signal in the crude extracellular mixture generated by live bacterial cells (see picture). These DNAzymes cleave a lone RNA linkage (R) embedded in a DNA chain and flanked by nucleotides labeled with a fluorophore (F) and a quencher (Q).

    20. NMR Spectroscopy

      Structure, Dynamics, and Kinetics of Weak Protein–Protein Complexes from NMR Spin Relaxation Measurements of Titrated Solutions (pages 3755–3759)

      Dr. Loïc Salmon, Dr. José-Luis Ortega Roldan, Dr. Ewen Lescop, Antoine Licinio, Prof. Nico van Nuland, Dr. Malene Ringkjøbing Jensen and Dr. Martin Blackledge

      Version of Record online: 18 MAR 2011 | DOI: 10.1002/anie.201100310

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      Making the invisible visible: Weak protein–protein interactions play a key role in a range of essential biological processes. However, transient or ultraweak complexes cannot be studied in detail by many biophysical techniques. A method based on the measurement of 15N relaxation rates can be used to study weak protein complexes (see picture; Dzz=diffusion tensor).

    21. Quaternary Centers

      Enantioselective Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters: Methodology and Applications (pages 3760–3763)

      Dr. Ravindra P. Sonawane, Dr. Vishal Jheengut, Dr. Constantinos Rabalakos, Dr. Robin Larouche-Gauthier, Helen K. Scott and Prof. Varinder K. Aggarwal

      Version of Record online: 4 MAR 2011 | DOI: 10.1002/anie.201008067

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      Pin it down: A range of substrates that bear versatile functional groups with quaternary stereogenic centers have been prepared with very high enantioselectivity from tertiary boronic esters (see scheme; Cb=N,N-diisopropylcarbamoyl, pin=pinacolato). The preparation of allylboronic esters bearing contiguous quaternary and tertiary stereogenic centers, and applications to natural product synthesis are also reported.

    22. High-Index Facets

      Anatase TiO2 Crystals with Exposed High-Index Facets (pages 3764–3768)

      Dr. Hai Bo Jiang, Qian Cuan, Ci Zhang Wen, Jun Xing, Di Wu, Prof. Dr. Xue-Qing Gong, Prof. Dr. Chunzhong Li and Prof. Dr. Hua Gui Yang

      Version of Record online: 17 MAR 2011 | DOI: 10.1002/anie.201007771

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      Put your best face forward: The performance of TiO2 anatase crystals in energy and environmental applications is normally correlated with the TiO2 crystal facets exposed, and increasing the percentage of highly reactive surfaces is extremely important. A new gas-phase oxidation process using TiCl4 as precursor now yields anatase TiO2 single crystals with primarily high-index {105} facets, which can cleave water photocatalytically.

    23. Oxygen Heterocycles

      Transition-Metal-Free Intramolecular Ullmann-Type O-Arylation: Synthesis of Chromone Derivatives (pages 3769–3773)

      Jie Zhao, Prof. Dr. Yufen Zhao and Prof. Dr. Hua Fu

      Version of Record online: 17 MAR 2011 | DOI: 10.1002/anie.201007302

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      Expect the upexpected: A transition-metal-free approach to access chromone derivatives has been developed. The intramolecular O-arylation of substituted 1-(2-haloaryl)-propane-1,3-diones in DMF in the presence of K2CO3 gave the corresponding target products in good to excellent yields (see scheme; DMF=N,N′-dimethylformamide).

    24. Organocatalysis

      Asymmetric One-Pot Four-Component Coupling Reaction: Synthesis of Substituted Tetrahydropyrans Catalyzed by Diphenylprolinol Silyl Ether (pages 3774–3779)

      Dr. Hayato Ishikawa, Satoshi Sawano, Yusuke Yasui, Yusuke Shibata and Prof. Dr. Yujiro Hayashi

      Version of Record online: 24 MAR 2011 | DOI: 10.1002/anie.201005386

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      Domino effect: The title reaction uses an asymmetric Michael/Henry reaction/acetalization/Lewis acid mediated allylation reaction to provide highly substituted tetrahydropyrans with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). All the carbon atoms in the tetrahydropyran ring are substituted with different groups, and the relative and absolute stereochemistry of the five contiguous carbon centers are completely controlled.

    25. Ferromagnetic Materials

      Spaced Heterometallic 3d–4f Magnetic Chains from the Pseudo-One-Dimensional Na2LnMnO(AsO4)2 Series: Stepped Magnetization in the Na2GdMnO(AsO4)2 Ferromagnet (pages 3780–3783)

      J. Palmer West, Dr. Wendy L. Queen, Dr. Shiou-Jyh Hwu and Katherine E. Michaux

      Version of Record online: 17 MAR 2011 | DOI: 10.1002/anie.201006672

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      Step it up: The Na2LnMnO(AsO4)2 series contains Ln-capped [MnO4] ferromagnetic chains, and the species with Ln=Gd reveals intriguing magnetic anomalies thought to be attributed to better structural confinement of the magnetic chains. It exhibits stepped magnetization and multiple-spin dynamics (see picture; Mn blue, Gd maroon, O red), two phenomena never before observed in a quasi-one-dimensional, 3d–4f condensed solid.

    26. Hypervalent Compounds

      Discovery of Stabilized Bisiodonium Salts as Intermediates in the Carbon–Carbon Bond Formation of Alkynes (pages 3784–3787)

      Dr. Toshifumi Dohi, Daishi Kato, Ryo Hyodo, Daisuke Yamashita, Dr. Motoo Shiro and Prof. Dr. Yasuyuki Kita

      Version of Record online: 21 MAR 2011 | DOI: 10.1002/anie.201007640

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      Ways and means to spirocycles: Pseudocyclic bisiodonium salts 1 stabilized by a secondary bonding interaction—an IIII⋅⋅⋅O⋅⋅⋅IIII pseudobridge linkage (circle) —were prepared by C[BOND]C bond formation between aryl alkynes and a μ-oxo-bridged hypervalent iodine compound. The synthetic utility of salts 1 was demonstrated by their facile conversion into functionalized spirocycles by treatment with a nucleophile.

    27. Reaction Optimization

      Self-Optimizing Continuous Reactions in Supercritical Carbon Dioxide (pages 3788–3792)

      Andrew J. Parrott, Dr. Richard A. Bourne, Dr. Geoffrey R. Akien, Dr. Derek J. Irvine and Prof. Martyn Poliakoff

      Version of Record online: 25 MAR 2011 | DOI: 10.1002/anie.201100412

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      Hands-free optimization: A combination of an automated flow reactor, online analysis, and a control algorithm leads to efficient optimization of reactions to a given product without the need for human intervention.

    28. Trifluoromethylation

      A Broadly Applicable Copper Reagent for Trifluoromethylations and Perfluoroalkylations of Aryl Iodides and Bromides (pages 3793–3798)

      Dr. Hiroyuki Morimoto, Tetsu Tsubogo, Dr. Nichole D. Litvinas and Prof. Dr. John F. Hartwig

      Version of Record online: 25 MAR 2011 | DOI: 10.1002/anie.201100633

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      Well compatible: The trifluoromethylations and perfluoroalkylations of aryl iodides and some aryl bromides with trifluoromethyl and perfluoroalkylcopper(I) phenanthroline complexes occur with broad scope at 25–50 °C (see scheme). The trifluoromethyl complex is prepared from inexpensive reagents and can be used in situ or isolated. The reactions tolerate a range of substituents and also occur with heteroaromatic systems.

    29. Ligand Design

      Cyclopropenylylidene-Stabilized Diaryl and Dialkyl Phosphenium Cations: Applications in Homogeneous Gold Catalysis (pages 3799–3802)

      Jekaterina Petuškova, Hans Bruns and Dr. Manuel Alcarazo

      Version of Record online: 14 MAR 2011 | DOI: 10.1002/anie.201100338

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      Cationic but electron-rich: Cyclopropenylylidene-stabilized phosphenium cations exhibit the electron richness of classical trialkyl and triaryl phosphines even though they carry a positive charge stemming from a cationic substituent directly bonded to the phosphorous atom. These two facts have been exploited to synthesize gold catalysts that can be easily recycled after use.

    30. Asymmetric Hydrogenation

      Ligand-Controlled Highly Regioselective and Asymmetric Hydrogenation of Quinoxalines Catalyzed by Ruthenium N-Heterocyclic Carbene Complexes (pages 3803–3806)

      Slawomir Urban, Dr. Nuria Ortega and Prof. Dr. Frank Glorius

      Version of Record online: 25 MAR 2011 | DOI: 10.1002/anie.201100008

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      Inflating flat bicycles: Proper choice of the N-heterocyclic carbene (NHC) ligand in Ru NHC complexes allows the completely regioselective ligand-controlled hydrogenation of either the heterocyclic or the carbocyclic ring of a substituted quinoxaline in quantitative yields. Chiral NHC ligands allow the challenging asymmetric hydrogenation of the carbocyclic ring of quinoxalines, yielding enantioenriched 5,6,7,8-tetrahydroquinoxalines with an enantiomeric ratio of up to 94:6.

    31. Solvent-Mediated Folding

      Spectroscopic Characterization of Solvent-Mediated Folding in Dicarboxylate Dianions (pages 3807–3810)

      Torsten Wende, Marius Wanko, Ling Jiang, Gerard Meijer, Knut R. Asmis and Angel Rubio

      Version of Record online: 24 MAR 2011 | DOI: 10.1002/anie.201006485

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      The relationship between conformational changes of suberate dianions in water clusters and the corresponding spectroscopic characteristics were studied theoretically and by IR spectroscopy (see picture for the charge displacement associated with the excitation of the carboxylate symmetric stretching modes). Folded structures are stabilized by the formation of additional hydrogen bonds between the solvated dianion and H2O molecules and should thus be retained in larger, microhydrated clusters.

    32. Signal Transduction

      Photoactivatable and Cell-Membrane-Permeable Phosphatidylinositol 3,4,5-Trisphosphate (pages 3811–3814)

      Dr. Matthias Mentel, Dr. Vibor Laketa, Dr. Devaraj Subramanian, Dr. Hartmut Gillandt and Dr. Carsten Schultz

      Version of Record online: 14 MAR 2011 | DOI: 10.1002/anie.201007796

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      Unleashed inside cells: The signaling molecule PI(3,4,5)P3 is prepared in a form that allows its cellular uptake and subsequent activation by light (see picture). The rapid eight-step synthetic sequence yields a stable derivative of the signaling molecule with high biological activity after deprotection (“uncaging”) with a laser flash, in live cells.

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Correspondence
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    15. Back Cover
    1. Back Cover: Magnetically Responsive Photonic Nanochains (Angew. Chem. Int. Ed. 16/2011) (page 3816)

      Yongxing Hu, Le He and Prof. Yadong Yin

      Version of Record online: 18 MAR 2011 | DOI: 10.1002/anie.201101594

      Thumbnail image of graphical abstract

      Magnetically responsive photonic nanochains composed of superparamagnetic Fe3O4 particles fixed within a silica shell are the smallest diffracting units that can operate in the visible spectrum. As Y. Yin et al. describe in their Communication on page 3747 ff., the synthesis involves magnetically forming chains of particles during silica coating and then wrapping them with additional silica to give mechanically robust and optically active rods.

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