Angewandte Chemie International Edition

Cover image for Vol. 47 Issue 21

May 13, 2008

Volume 47, Issue 21

Pages 3843–4027

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
    10. Preview
    1. Cover Picture: Designed Synthesis of POM–Organic Frameworks from {Ni6PW9} Building Blocks under Hydrothermal Conditions (Angew. Chem. Int. Ed. 21/2008) (page 3843)

      Shou-Tian Zheng, Jie Zhang and Guo-Yu Yang

      Version of Record online: 6 MAY 2008 | DOI: 10.1002/anie.200890095

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      Rigid carboxylate linkers allow the orientated aggregation of Ni6-substituted polyoxotungstates under hydrothermal conditions, as G.-Y. Yang et al. describe in their Communication on page 3909 ff. The syntheses lead to unusual one, two, and three-dimensional organic polyoxometallte structures formed of monomeric, dimeric, or polymeric helical secondary structural units.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
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    1. Inside Cover: Supramolecular Block Copolymers with Cucurbit[8]uril in Water (Angew. Chem. Int. Ed. 21/2008) (page 3844)

      Urs Rauwald and Oren A. Scherman

      Version of Record online: 6 MAY 2008 | DOI: 10.1002/anie.200890096

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      Supramolecular diblock copolymers can be easily formed using the container molecule cucurbit[8]uril, which functions as a supramolecular “handcuff” by “shackling up” the chain ends of two homopolymers. O. A. Scherman and U. Rauwald describe in their Communication on page 3950 ff. how polymer chains can be bound by a stimulus-responsive ternary host–guest complex and thus form dynamic block copolymers. Amphiphilic polymer blocks can result in self-organization to more highly ordered, compartmentalized structures, such as micelles and vesicles.

  3. Graphical Abstract

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

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

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

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    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
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    1. Fluorous Tags Catching on Microarrays (pages 3868–3870)

      Nicola L. Pohl

      Version of Record online: 17 APR 2008 | DOI: 10.1002/anie.200704801

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      Tag team: Not only hydrophilic carbohydrates but also hydrophobic compounds such as histone deacetylase inhibitors and biotin can be incorporated into fluorous-based small-molecule microarrays. A range of fluorous-tagged molecules can be patterned and screened for bioactivity on a fluorous surface with hit rates comparable to those seen by solution-based and surface plasmon resonance-based bioassays.

    2. Rational Engineering of Dynamic DNA Systems (pages 3871–3873)

      Udo Feldkamp and Christof M. Niemeyer

      Version of Record online: 21 APR 2008 | DOI: 10.1002/anie.200800675

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      Opening time: A method for the systematic and automatable design of DNA hybridization networks was recently introduced, which was based on the catalytic opening of metastable hairpin loops (see scheme). This technique has various applications in nanobiotechnology, such as the stepwise self-assembly of DNA scaffolds and the engineering of dynamic DNA devices.

  7. Review

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    9. Communications
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    1. How Is Oxygen Incorporated into Oxides? A Comprehensive Kinetic Study of a Simple Solid-State Reaction with SrTiO3 as a Model Material (pages 3874–3894)

      Rotraut Merkle and Joachim Maier

      Version of Record online: 21 APR 2008 | DOI: 10.1002/anie.200700987

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      O, how does it go? Equilibration of an oxide with the surrounding oxygen partial pressure is one of the simplest gas–solid reactions. Nevertheless, it is a complex process comprising a (multistep) surface reaction, chemical bulk diffusion, and transport across or along grain boundaries. This Review gives a detailed phenomenological as well as mechanistic description of these processes for the model perovskite oxide SrTiO3 emphasizing their relevance for electrochemical devices.

  8. Communications

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
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    1. An All-Inorganic, Stable, and Highly Active Tetraruthenium Homogeneous Catalyst for Water Oxidation (pages 3896–3899)

      Yurii V. Geletii, Bogdan Botar, Paul Kögerler, Daniel A. Hillesheim, Djamaladdin G. Musaev and Craig L. Hill

      Version of Record online: 19 MAR 2008 | DOI: 10.1002/anie.200705652

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      Oxidation without organics: A tetraruthenium polyoxometalate (see picture; Ru blue, O red, Si yellow, W black) catalyzes the rapid oxidation of H2O to O2 in water at ambient temperature, and shows considerable stability under turnover conditions. The complex was characterized by several methods, including X-ray crystallography and cyclic voltammetry.

    2. Clockwork PCR Including Sample Preparation (pages 3900–3904)

      Juergen Pipper, Yi Zhang, Pavel Neuzil and Tseng-Ming Hsieh

      Version of Record online: 15 APR 2008 | DOI: 10.1002/anie.200705016

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      For whom the bell tolls: Surface-functionalized superparamagnetic particles emulsified in mineral oil turn a free-standing droplet into a flexible virtual laboratory with (sub)microliter volumes. By using magnetic forces, rare acute monocytic leukaemia cells are extracted from blood, preconcentrated, purified, lysed, and subjected to a real-time PCR in minutes. The PCR works like a clockwork by rotating the droplet over different temperature zones.

    3. Two-Phase (Bio)Catalytic Reactions in a Table-Top Centrifugal Contact Separator (pages 3905–3908)

      Gerard N. Kraai, Floris van Zwol, Boelo Schuur, Hero J. Heeres and Johannes G. de Vries

      Version of Record online: 15 APR 2008 | DOI: 10.1002/anie.200705426

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      A new spin on catalysis: A table-top centrifugal contact separator allows for fast continuous two-phase reactions to be performed by intimately mixing two immiscible phases and then separating them. Such a device has been used to produce biodiesel from sunflower oil and MeOH/NaOMe. A lipase-catalyzed esterification of oleic acid with nBuOH (see picture) also proceeds with high conversion and can be run for up to 13 h.

    4. Designed Synthesis of POM–Organic Frameworks from {Ni6PW9} Building Blocks under Hydrothermal Conditions (pages 3909–3913)

      Shou-Tian Zheng, Jie Zhang and Guo-Yu Yang

      Version of Record online: 20 MAR 2008 | DOI: 10.1002/anie.200705709

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      Directed combination of {Ni6PW9} building blocks with various rigid carboxylate linkers under hydrothermal conditions yields a series of unprecedented polyoxometalate–organic frameworks (POMOFs) with remarkable structural diversity including 1D, 2D, and 3D structures based on monomers, dimers, or infinite helical chains (see picture for 3D structure: WO6: red; NiO6: green; PO4: yellow; 1,2,4-benzenetricarboxylate: gold).

    5. Kinetic Gate-Opening Process in a Flexible Porous Coordination Polymer (pages 3914–3918)

      Daisuke Tanaka, Keiji Nakagawa, Masakazu Higuchi, Satoshi Horike, Yoshiki Kubota, Tatsuo C. Kobayashi, Masaki Takata and Susumu Kitagawa

      Version of Record online: 11 APR 2008 | DOI: 10.1002/anie.200705822

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      Open the gate! A porous coordination polymer shows abrupt changes in its adsorption isotherm with guest-dependent gate-opening pressure (see picture). Kinetic analysis reveals that adsorption with structure transformation follows a gate-opening model, in which adsorption proceeds through the formation of an intermediate by a gate-opening process. This process provides a significant difference in onset pressure between similar gas molecules.

    6. Cholesterol seco-Sterol-Induced Aggregation of Methylated Amyloid-β Peptides—Insights into Aldehyde-Initiated Fibrillization of Amyloid-β (pages 3919–3922)

      Johanna C. Scheinost, Hong Wang, Grant E. Boldt, John Offer and Paul Wentworth Jr.

      Version of Record online: 11 APR 2008 | DOI: 10.1002/anie.200705922

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      Hot spot on amyloid-β? Atheronal-B-induced aggregation of amyloid-β (Aβ) involves a site-specific adduction of the aldehyde to the ε-amino group of Lys 16, suggesting that Lys 16 is a hot spot for atheronal-induced fibrillization of Aβ (see scheme). This process can be inhibited by molecules like cholesterol that compete for the central hydrophobic cluster binding domain.

    7. Color Change of Proteorhodopsin by a Single Amino Acid Replacement at a Distant Cytoplasmic Loop (pages 3923–3926)

      Maiko Yoshitsugu, Mikihiro Shibata, Daisuke Ikeda, Yuji Furutani and Hideki Kandori

      Version of Record online: 11 APR 2008 | DOI: 10.1002/anie.200705989

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      Switching from red to pink: It has been believed that only the amino acids near the retinal chromophore are responsible for the color tuning of rhodopsins. Herein is reported a color change of proteorhodopsin, an archaeal-type rhodopsin in marine bacteria, by mutation of Ala178 to Arg at the E–F loop. The red shift at a neutral pH value amounts to 20 nm (see graph).

    8. Optical Analysis of Hg2+ Ions by Oligonucleotide–Gold-Nanoparticle Hybrids and DNA-Based Machines (pages 3927–3931)

      Di Li, Agnieszka Wieckowska and Itamar Willner

      Version of Record online: 11 APR 2008 | DOI: 10.1002/anie.200705991

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      Strand and deliver: Two different optical methods to analyze Hg2+ ions based on the formation of thymine–Hg2+ complexes are developed. These methods include the analysis of Hg2+ ions by using aggregated gold nanoparticles and by using a DNA-based machine (see scheme).

    9. The Molecular Cluster [Bi10Au2](SbBi3Br9)2 (pages 3932–3935)

      Bernhard Wahl, Lars Kloo and Michael Ruck

      Version of Record online: 15 APR 2008 | DOI: 10.1002/anie.200800142

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      A multitude of new binding modes: A [Bi10Au2]6+ heteroicosahedron and two (SbBi3Br9)3− hemispheres form molecular cluster [Bi10Au2](SbBi3Br9)2 (see picture: Bi blue, Au yellow, Sb green, Br dark red). The [Bi10Au2]6+ polycation involves significant bismuth–gold interactions. The molecule also exhibits a rare interpnicogen covalent bond between bismuth and antimony and a complex donor–acceptor bond between the anionic caps and the polycation.

    10. Mutasynthesis of Fluorosalinosporamide, a Potent and Reversible Inhibitor of the Proteasome (pages 3936–3938)

      Alessandra S. Eustáquio and Bradley S. Moore

      Version of Record online: 14 APR 2008 | DOI: 10.1002/anie.200800177

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      A knockout result: Fluorine substituents give drugs beneficial properties. By using a rational combination of genetic engineering and precursor-directed biosynthesis, fluorosalinosporamide (see scheme) was generated in a fermentation-based approach. The anticancer lead compound and marine natural product salinosporamide A is chlorinated. A comparison of the biological activity of these proteasome inhibitors is presented.

    11. Substituent Effects, Reactant Preorganization, and Ligand Exchange Control the Reactivity in RhI-Catalyzed (5+2) Cycloadditions between Vinylcyclopropanes and Alkynes (pages 3939–3941)

      Peng Liu, Paul Ha-Yeon Cheong, Zhi-Xiang Yu, Paul A. Wender and Kendall N. Houk

      Version of Record online: 15 APR 2008 | DOI: 10.1002/anie.200800420

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      Heteroatom and bulky alkyl substituents dramatically increase the rate of RhI-catalyzed (5+2) cycloadditions of 1. This fact could be attributed to steric effects which ease the reactant preorganization, and to the stabilization of the allyl intermediate by (hyper)conjugation with the substituents. The methoxy- and isopropyl-substituted 1 have an activation energy 5 and 7 kcal mol−1, respectively, lower than the unsubstituted vinylcyclopropane.

    12. Self-Assembly of Supramolecular Luminescent AuI–CuI Complexes: “Wrapping” an Au6Cu6 Cluster in a [Au3(diphosphine)3]3+ “Belt” (pages 3942–3945)

      Igor O. Koshevoy, Laura Koskinen, Matti Haukka, Sergey P. Tunik, Pavel Yu. Serdobintsev, Alexey S. Melnikov and Tapani A. Pakkanen

      Version of Record online: 14 APR 2008 | DOI: 10.1002/anie.200800452

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      Belt and suspenders: A supramolecular gold–copper cluster has been synthesized by Cu+-assisted self-assembly of [Au(C2Ph)2] rods and a gold–diphosphine belt, which is suspended from the Au6Cu6 core by Au[BOND]Au bonds (see picture). The cluster displays strong orange luminescence on excitation at 308 nm which is more intense than that of either of its structural fragments, which were isolated and studied independently. P-P=Ph2PC6H4C6H4PPh2.

    13. A Supramolecular Catalyst for the Decarboxylative Hydroformylation of α,β-Unsaturated Carboxylic Acids (pages 3946–3949)

      Tomáš Šmejkal and Bernhard Breit

      Version of Record online: 16 APR 2008 | DOI: 10.1002/anie.200800956

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      Head 'em up, move 'em out, aldehyde! A catalytic transformation of α,β-unsaturated carboxylic acids into aldehydes through a hydroformylation–decarboxylation process has been developed (see scheme; Do=donor ligand, FG1 and FG2=complementary functional groups). The reaction proceeds at mild conditions, tolerates many functional groups, and liberates CO2 as the only stoichiometric by-product.

    14. Supramolecular Block Copolymers with Cucurbit[8]uril in Water (pages 3950–3953)

      Urs Rauwald and Oren A. Scherman

      Version of Record online: 28 APR 2008 | DOI: 10.1002/anie.200705591

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      Be my guest! A supramolecular amphiphilic diblock copolymer was prepared with a cucurbit[8]uril molecular “handcuff” (see picture). It subsequently undergoes a hierarchical self-assembly process, resulting in the formation of a tertiary, compartmentalized nanostructure.

    15. Exploring Crystal Morphology of Nanoporous Hosts from Time-Dependent Guest Profiles (pages 3954–3957)

      Despina Tzoulaki, Lars Heinke, Wolfgang Schmidt, Ursula Wilczok and Jörg Kärger

      Version of Record online: 21 APR 2008 | DOI: 10.1002/anie.200705597

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      The persistence of resistance: In the zeolite silicalite-1, the influence of transport barrier on the surface and between crystal segments, are negligibly small in comparison to the transport resistance of the intracrystalline pore system. Diffusion experiments are conducted with these zeolite crystals and intracrystalline diffusion coefficients of guest molecules determined.

    16. “Carbocation Watching” in Solvolysis Reactions (pages 3958–3961)

      Heike F. Schaller and Herbert Mayr

      Version of Record online: 28 APR 2008 | DOI: 10.1002/anie.200800354

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      The missing link between conventional SN1 reactions and the chemistry of stable carbocations has been found. When water is added to the colorless solution of the covalent compound Ar2CH-OAc (Ar=morpholinophenyl) in acetone, the appearance and disappearance of the intermediate carbocation ArCH+ can be observed with the naked eye!

    17. Controlled Generation of Hydrogen from Formic Acid Amine Adducts at Room Temperature and Application in H2/O2 Fuel Cells (pages 3962–3965)

      Björn Loges, Albert Boddien, Henrik Junge and Matthias Beller

      Version of Record online: 6 MAY 2008 | DOI: 10.1002/anie.200705972

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      Forever blowing bubbles: Hydrogen is generated from formic acid amine adducts at room temperature used directly in fuel cells (see picture for apparatus). Ruthenium phosphine systems act as catalysts in this transformation.

    18. A Viable Hydrogen-Storage System Based On Selective Formic Acid Decomposition with a Ruthenium Catalyst (pages 3966–3968)

      Céline Fellay, Paul J. Dyson and Gábor Laurenczy

      Version of Record online: 4 APR 2008 | DOI: 10.1002/anie.200800320

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      The use of formic acid as a hydrogen-storage material has become more feasible thanks to the development of a homogeneous catalytic system of ruthenium water-soluble complexes (Ru/TPPTS; TPPTS=meta-trisulfonated triphenylphosphine) that selectively decomposes HCOOH into H2 and CO2. Continuous generation of H2 of very high purity, over a wide range of pressures, and under mild conditions was achieved.

    19. Growing Molecular Crystals on Inorganic Crystals: Polar Structure Induced by Noncentrosymmetric Templates (pages 3969–3972)

      M. Jaya Prakash, Pallepogu Raghavaiah, Y. S. R. Krishna and T. P. Radhakrishnan

      Version of Record online: 15 APR 2008 | DOI: 10.1002/anie.200704031

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      Like promotes like: The templating effect of inorganic crystals is exploited to promote the growth of the polar structure of a molecular crystal of a dipolar zinc(II) complex (see picture). It is likely that the polar nature of the noncentrosymmetric template crystal lattice, and its associated electrostatic field, facilitates the oriented assembly of the dipolar molecules.

    20. Janus Colloids Formed by Biphasic Grafting at a Pickering Emulsion Interface (pages 3973–3975)

      Bing Liu, Wei Wei, Xiaozhong Qu and Zhenzhong Yang

      Version of Record online: 17 APR 2008 | DOI: 10.1002/anie.200705103

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      A two-faced synthesis: Biphasic grafting at a Pickering emulsion interface leads to the formation of Janus colloids (see scheme; ATRP: atom transfer radical polymerization), which form Janus composite colloids by the preferential growth of desired materials in specific regions of the original colloids. This approach is general and can be extended to the synthesis of a huge family of such colloids.

    21. Heterotrimetallic Salts: Synthesis, Structures, and Superbase Reactivity of Crystalline tert-Butoxides [Li4Na2K2(OtBu)8(μ-L)]n (pages 3976–3978)

      Xuehong Wei, Qingchen Dong, Hongbo Tong, Jianbin Chao, Diansheng Liu and Michael F. Lappert

      Version of Record online: 10 APR 2008 | DOI: 10.1002/anie.200705268

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      Line them up! Crystalline, polymeric arrays of heterotrimetallic (Li4Na2K2) tert-butoxides of definite composition have been obtained by mixing the individual Li, Na, and K alkoxides. In the crystal, [Li4Na2K23-OtBu)64-OtBu)2] units (see picture: Li blue, Na green, K purple, C white, O red) are joined through their terminal K ions by η66-C6H6 or N,N′-tetramethylethylenediamine bridges.

    22. Catalytic Synthesis of β3-Amino Acid Derivatives from α-Amino Acids (pages 3979–3983)

      Christopher M. Byrne, Tamara L. Church, John W. Kramer and Geoffrey W. Coates

      Version of Record online: 11 APR 2008 | DOI: 10.1002/anie.200705310

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      α goes to β! The catalytic ring-expansive carbonylation of oxazolines, easily derived from α-amino acids, to yield β-amino acid derivatives is described. The catalyst is [HCo(CO)4]; high yields are observed for most substrates, and enantiopure oxazolines are carbonylated with predictable stereochemistry to the corresponding enantiopure oxazinones.

    23. Controlling the Growth of Charged-Nanoparticle Chains through Interparticle Electrostatic Repulsion (pages 3984–3987)

      Hao Zhang and Dayang Wang

      Version of Record online: 11 APR 2008 | DOI: 10.1002/anie.200705537

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      An electrostatic tuner: Long-range isotropic electrostatic repulsion between identically charged nanoparticles can become anisotropic in the presence of short-range anisotropic dipolar interactions, thus endorsing anisotropic self-assembly of the nanoparticles into chains. The length of these particle chains can be tuned by controlling the interparticle electrostatic repulsion (see image).

    24. Macrocyclic High-Spin (S=2) Molecule: Spin Identification of a Sterically Rigid Metacyclophane-Based Nitroxide Tetraradical by Two-Dimensional Electron Spin Transient Nutation Spectroscopy (pages 3988–3990)

      Takatoshi Sawai, Kazunobu Sato, Tomoaki Ise, Daisuke Shiomi, Kazuo Toyota, Yasushi Morita and Takeji Takui

      Version of Record online: 15 APR 2008 | DOI: 10.1002/anie.200705583

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      A spin quintet: The electronic and molecular structure of the metacyclophane-based spin-quintet tetraradical 1 with a sterically controlled rigid structure and small fine-structure parameters is characterized. Pulse-ESR based 2D electron spin nutation spectroscopy allows the spin multiplicity of 1 to be unequivocally identified, providing its fine-structure parameters and g-values.

    25. High Catalytic Activity of Dendritic C60 Monoadducts in Metal-Free Superoxide Dismutation (pages 3991–3994)

      Gao-Feng Liu, Miloš Filipović, Ivana Ivanović-Burmazović, Florian Beuerle, Patrick Witte and Andreas Hirsch

      Version of Record online: 14 APR 2008 | DOI: 10.1002/anie.200800008

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      Fullerene antioxidants: A direct correlation between the redox and structural properties of water-soluble fullerenes (see picture) and their reactivity towards superoxide is demonstrated. Some of the C60 monoadducts examined act as superoxide dismutase mimetics. The findings establish a guide for designing fullerene derivatives to catalytically decompose the superoxide radical anion.

    26. Benzopyrenomycin, a Cytotoxic Bacterial Polyketide Metabolite with a Benzo[a]pyrene-Type Carbocyclic Ring System (pages 3995–3998)

      Xueshi Huang, Jian He, Xuemei Niu, Klaus-Dieter Menzel, Hans-Martin Dahse, Susanne Grabley, Hans-Peter Fiedler, Isabel Sattler and Christian Hertweck

      Version of Record online: 15 APR 2008 | DOI: 10.1002/anie.200800083

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      A natural benzopyren: The title compound 1 was discovered by chemical metabolite profiling of a large-scale fermentation of Streptomyces lavendulae. Biological evaluation of the peri-fused pentacyclic compound revealed antitumor activity against several cell lines. The co-occurrence of an angucyclic polyketide with an identical ring-substitution pattern suggests that 1 is biosynthesized from an angular decaketide and a C3 building block.

    27. Structural Complexity in Intermetallic Alloys: Long-Periodic Order beyond 10 nm in the System BaSn3/BaBi3 (pages 3999–4004)

      Siméon Ponou, Thomas F. Fässler and Lorenz Kienle

      Version of Record online: 17 APR 2008 | DOI: 10.1002/anie.200800378

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      Nanosized long-periodic stacking sequences are formed by polytypic transformations that are initiated by partially substituting Bi for Sn in the close-packed structure of BaSn3. Single-crystal X-ray diffraction and TEM investigations show that temperature-dependent interlayer-ordering processes lead to repeat units beyond 10 nm (see TEM image).

    28. Total Synthesis of Macbecin I (pages 4005–4008)

      Justin K. Belardi and Glenn C. Micalizio

      Version of Record online: 11 APR 2008 | DOI: 10.1002/anie.200800400

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      Beyond the bounds of biosynthesis: In a step towards the goal of developing a synthetic pathway for the production of collections of complex molecules related to the benzoquinone ansamycin antibiotics, a natural member of this class was synthesized in a convergent manner through the mild titanium alkoxide mediated coupling of the highly functionalized aniline-containing alkyne 1 with the sensitive polyunsaturated aldehyde 2.

    29. A Carbonyl Ylide Cycloaddition Approach to Platensimycin (pages 4009–4011)

      Chan Hyuk Kim, Ki Po Jang, Soo Young Choi, Young Keun Chung and Eun Lee

      Version of Record online: 15 APR 2008 | DOI: 10.1002/anie.200800568

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      Short and to the point: A formal synthesis of platensimycin has been accomplished by employing a carbonyl ylide [3+2] cycloaddition reaction (see scheme). This short and facile enantioselective synthesis of the pivotal tetracyclic precursor requires 11 steps and proceeds in 20 % overall yield from isopropyl cyanoacetate.

    30. Diphenylprolinol Silyl Ether as a Catalyst in an Enantioselective, Catalytic, Formal Aza [3+3] Cycloaddition Reaction for the Formation of Enantioenriched Piperidines (pages 4012–4015)

      Yujiro Hayashi, Hiroaki Gotoh, Ryouhei Masui and Hayato Ishikawa

      Version of Record online: 10 APR 2008 | DOI: 10.1002/anie.200800662

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      Aza-ene reaction: Diphenylprolinol silyl ether was found to be an effective organocatalyst for the formal aza [3+3] cycloaddition reaction of α,β-unsaturated aldehydes and enecarbamates (see scheme). The reaction proceeds through an asymmetric catalytic ene reaction, isomerization, hydrolysis, and cyclization to afford piperidine derivatives in good yields and excellent enantioselectivities.

    31. Chiral Phosphoric Acid Catalyzed Enantioselective Friedel–Crafts Alkylation of Indoles with Nitroalkenes: Cooperative Effect of 3 Å Molecular Sieves (pages 4016–4018)

      Junji Itoh, Kohei Fuchibe and Takahiko Akiyama

      Version of Record online: 16 APR 2008 | DOI: 10.1002/anie.200800770

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      Crafty catalysts: Friedel–Crafts alkylation of indoles with nitroalkenes proceeded in the presence of phosphoric acid 1 and 3 Å molecular sieves to give Friedel–Crafts adducts with excellent enantioselectivities (see scheme).

    32. Fluorescent Naphthyl- and Anthrylazoles from the Catalytic Coupling of Phenylazoles with Internal Alkynes through the Cleavage of Multiple C[BOND]H Bonds (pages 4019–4022)

      Nobuyoshi Umeda, Hayato Tsurugi, Tetsuya Satoh and Masahiro Miura

      Version of Record online: 16 APR 2008 | DOI: 10.1002/anie.200800924

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      Bright light rings: The direct coupling of phenylazoles with an internal alkyne proceeds efficiently in the presence of a rhodium catalyst and a copper oxidant to selectively give either the 1-naphthyl- or 1-anthrylazole derivatives through the cleavage of multiple C[BOND]H bonds (see scheme; 1-naphthylazole derivative not shown). Some of the products exhibit intense fluorescence in the solid state.

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