Angewandte Chemie International Edition

Cover image for Vol. 45 Issue 12

March 13, 2006

Volume 45, Issue 12

Pages 1821–1987

    1. Cover Picture: Biomimetic Fluorapatite–Gelatine Nanocomposites: Pre-Structuring of Gelatine Matrices by Ion Impregnation and Its Effect on Form Development / Intrinsic Electric Dipole Fields and the Induction of Hierarchical Form Developments in Fluorapatite–Gelatine Nanocomposites: A General Principle for Morphogenesis of Biominerals? (Angew. Chem. Int. Ed. 12/2006) (page 1821)

      Harald Tlatlik, Paul Simon, Agnieszka Kawska, Dirk Zahn, Rüdiger Kniep and Hannes Lichte

      Version of Record online: 6 MAR 2006 | DOI: 10.1002/anie.200690040

      Form development…during growth of fluorapatite–gelatine nanocomposites is effected by pre-structuring of gelatine matrices by ion impregnation. The cover picture shows the hierarchical fractal aggregate (background), structural details of a fanlike aggregate, and a simulation of the “stiffening” effect on a protein molecule of Ca2+ ion incorporation. This effect is discussed by R. Kniep and co-workers in their Communication on page 1905 ff. A second paper on page 1911 ff. deals with the effect of intrinsic electric dipole fields on the form development of the nanocomposite materials.

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      Molecular Recognition of a Three-Way DNA Junction by a Metallosupramolecular Helicate (page 1834)

      Aneta Oleksy, Alexandre G. Blanco, Roeland Boer, Isabel Usón, Joan Aymamí, Alison Rodger, Michael J. Hannon and Miquel Coll

      Version of Record online: 6 MAR 2006 | DOI: 10.1002/anie.200690042

      This article corrects:

      Molecular Recognition of a Three-Way DNA Junction by a Metallosupramolecular Helicate1

      Vol. 45, Issue 8, 1227–1231, Version of Record online: 6 FEB 2006

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      Transcription and Amplification of Molecular Chirality to Oppositely Biased Supramolecular π Helices (page 1834)

      Ayyappanpillai Ajayaghosh, Reji Varghese, Subi Jacob George and Chakkooth Vijayakumar

      Version of Record online: 6 MAR 2006 | DOI: 10.1002/anie.200690044

      This article corrects:
    4. Aldol Reactions within the RNA World (pages 1838–1840)

      Magnus Rueping

      Version of Record online: 6 MAR 2006 | DOI: 10.1002/anie.200504053

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      Keep the fire burning: It is hard to find new aspects to the aldol reaction, as a wealth of diastereoselective and enantioselective examples with a range of catalysts are known. However, recent work on template-mediated cross-aldol reactions and ribozyme-catalyzed aldol reactions show that this topic is still hot. Both reports are relevant to the theory of the RNA world.

    5. Transition-Metal Catalysis as a Tool for the Covalent Labeling of Proteins (pages 1841–1843)

      Jan H. van Maarseveen, Joost N. H. Reek and Jaap Willem Back

      Version of Record online: 22 FEB 2006 | DOI: 10.1002/anie.200504352

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      They make a good couple: Protein modification the transition-metal catalysis enables the selective labeling of proteins and has been demonstrated in complex mixtures. Current examples of such coupling reactions are the Ir-catalyzed reductive amination of lysine residues and the alkylation of tryptophan residues by Rh carbenes in proteins under aqueous conditions (see scheme).

    6. The Reactivity–Selectivity Principle: An Imperishable Myth in Organic Chemistry (pages 1844–1854)

      Herbert Mayr and Armin R. Ofial

      Version of Record online: 7 FEB 2006 | DOI: 10.1002/anie.200503273

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      Fact or Myth? Selectivity is the distance between the correlation lines for two substrates Bj. You may confirm by trial that it is impossible to draw a large number of non-intersecting correlation lines on this graph, all of which converge when going from left to right, as required by the still widely accepted reactivity–selectivity principle (RSP).

    7. Rational Design of DNA Nanoarchitectures (pages 1856–1876)

      Udo Feldkamp and Christof M. Niemeyer

      Version of Record online: 10 FEB 2006 | DOI: 10.1002/anie.200502358

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      In the past 20 years, DNA has been established as a powerful material for molecular constructions at the nanometer scale. The ability to design building blocks from DNA containing well-defined secondary structure motifs (a–f, in the scheme) allows the assembly of large supramolecular arrays, scaffolds, and even mechanical and logical nanodevices.

    8. Prototype of a Photoswitchable Foldamer (pages 1878–1881)

      Anzar Khan, Christian Kaiser and Stefan Hecht

      Version of Record online: 20 JAN 2006 | DOI: 10.1002/anie.200503849

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      Know where to fold 'em: A foldamer exhibiting a light-induced helix–coil transition (see scheme) can be constructed by introducing a photochromic azobenzene moiety (red) into the center of an amphiphilic phenylene ethynylene backbone (blue). This system gives insight into folding and unfolding mechanisms and promises applications in photoresponsive (bio)materials and “smart” delivery devices based on photoresponsive dynamic receptors.

    9. Undressing of Phosphine Gold(I) Complexes as Irreversible Inhibitors of Human Disulfide Reductases (pages 1881–1886)

      Sabine Urig, Karin Fritz-Wolf, Régis Réau, Christel Herold-Mende, Katalin Tóth, Elisabeth Davioud-Charvet and Katja Becker

      Version of Record online: 22 FEB 2006 | DOI: 10.1002/anie.200502756

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      Redox-based chemotherapy: The irreversible inhibition of human glutathione reductase results in a unique S-AuI-S coordination, which was determined crystallographically. The chemotherapeutic potential of phosphine–metal complexes was probed by kinetic analysis of the fast and effective inhibition of redox enzymes as well as by DNA-interaction studies and cell-proliferation tests.

    10. The Molecular Solid Sc24C10I30: A Truncated, Hollow T4 Supertetrahedron of Iodine Filled with a T3 Supertetrahedron of Scandium That Encapsulates the Adamantoid Cluster Sc4C10 (pages 1886–1889)

      Liesbet Jongen, Anja-Verena Mudring and Gerd Meyer

      Version of Record online: 17 FEB 2006 | DOI: 10.1002/anie.200503914

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      Like a Russian doll: In the nanomolecule Sc24C10I30, an outer I30 envelope (pink) surrounds a Sc20 T3 supertetrahedron (blue), which is filled by a C10 T2 supertetrahedron (gray), which, in turn, is filled by a Sc4 T1 tetrahedron (light gray), containing two electrons in a four-center, two-electron bond.

    11. Thermostable and Monoconjugable Gold Clusters with a Dodecadentate Thioether Ligand Gripper (pages 1889–1891)

      Wolf Matthias Pankau, Sven Mönninghoff and Günter von Kiedrowski

      Version of Record online: 22 FEB 2006 | DOI: 10.1002/anie.200502370

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      Get a grip: A tailor-made ligand bearing 12 thioether groups can act as a “gripper” for the Au55 cluster to give thermally stable, monofunctionalized labels for biomolecules (see scheme). Conjugates of the gold cluster with DNA strands can act as efficient fluorescence quenchers and can survive the harsh thermal conditions of PCR experiments.

    12. Decomposition of Thymidine by Low-Energy Electrons: Implications for the Molecular Mechanisms of Single-Strand Breaks in DNA (pages 1893–1896)

      Sylwia Ptasińska, Stephan Denifl, Sascha Gohlke, Paul Scheier, Eugen Illenberger and Tilmann D. Märk

      Version of Record online: 28 FEB 2006 | DOI: 10.1002/anie.200503930

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      The damage to biological systems by high-energy quanta occurs mainly through secondary species created in the ionization path. Interaction of the low-energy (0–3 eV) electrons with thymidine (Td) in the gas phase was investigated. These electrons induce loss of hydrogen from the N3 position and scission of the N1[BOND]C1 bond. The transfer of excess electrons, initially localized on thymine, to the sugar moiety was not observed.

    13. The First Gold-Catalyzed C[BOND]S Bond Formation: Cycloisomerization of α-Thioallenes to 2,5-Dihydrothiophenes (pages 1897–1899)

      Nobuyoshi Morita and Norbert Krause

      Version of Record online: 17 FEB 2006 | DOI: 10.1002/anie.200503846

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      One good ring deserves another: A highly efficient and stereoselective cycloisomerization of α-thioallenes to 2,5-dihydrothiophenes is the first example of a gold-catalyzed carbon–sulfur bond formation (see scheme, X=Cl, I). Both gold(I) and gold(III) salts can be used as the precatalyst, with AuCl and AuI giving the best yields. The method is of interest for the stereoselective synthesis of biologically active 2,5-disubstituted dihydro- or tetrahydrothiophenes.

    14. Sequential Catalysis: A Metathesis/Dihydroxylation Sequence (pages 1900–1903)

      Samuel Beligny, Stefan Eibauer, Simon Maechling and Siegfried Blechert

      Version of Record online: 10 FEB 2006 | DOI: 10.1002/anie.200503552

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      A real step-saver: A single ruthenium–carbene complex catalyzes a sequence of two reactions, namely, a metathesis reaction (ring-closing or cross metathesis) and subsequent dihydroxylation of the newly formed double bond. A variety of cyclic and acyclic cis-diols were prepared in good yields (see scheme). This new methodology provides an interesting alternative to the pinacol coupling.

    15. A Hexanuclear Ytterbium Complex Anion with Fourteen Azido Ligands (pages 1903–1905)

      Marc D. Walter, Frank Weber, Gotthelf Wolmershäuser and Helmut Sitzmann

      Version of Record online: 22 FEB 2006 | DOI: 10.1002/anie.200503986

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      Bridge to ytterbium: In the hexanuclear cluster ion [(4CpYb)6(N3)14]2− (4Cp= C5H(CHMe2)4), the Yb3+ centers are arranged in a distorted octahedron (see Figure; Yb red, N blue, C white). The twelve edges of the octahedron are bridged by ten μ1,3-N3 and two μ1,1-N3 ligands. Two additional azido ligands located within the cluster cavity act as μ1,1,3-N3 bridges.

    16. Biomimetic Fluorapatite–Gelatine Nanocomposites: Pre-Structuring of Gelatine Matrices by Ion Impregnation and Its Effect on Form Development (pages 1905–1910)

      Harald Tlatlik, Paul Simon, Agnieszka Kawska, Dirk Zahn and Rüdiger Kniep

      Version of Record online: 22 FEB 2006 | DOI: 10.1002/anie.200503610

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      Form follows the ion: The morphogenesis of fluorapatite–gelatine nanocomposites is studied from both electron microscopy and atomistic simulation revealing ion impregnation effects on the growth mechanisms. Depending on the ionic species used for pre-treatment of the organic component dramatic changes of the mesoscopic structuring are observed.

    17. Intrinsic Electric Dipole Fields and the Induction of Hierarchical Form Developments in Fluorapatite–Gelatine Nanocomposites: A General Principle for Morphogenesis of Biominerals? (pages 1911–1915)

      Paul Simon, Dirk Zahn, Hannes Lichte and Rüdiger Kniep

      Version of Record online: 22 FEB 2006 | DOI: 10.1002/anie.200504465

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      The seeder of the pack: The electrical potential distribution (see phase image of an electron hologram) around the basal plane close to the prism faces of a hexagonal fluorapatite–gelatine nanocomposite seed influences the growth of the nanocomposite. The seed consists of elementary dipoles on the nanometer scale, which all have the same orientation along the c axis of the composite seed. Further form development of the seed leads to fractal patterns.

    18. Molecular and Supramolecular Homochirality: Enantiopure Perfluorocarbon Rotamers and Halogen-Bonded Fluorous Double Helices (pages 1915–1918)

      Alessandro Casnati, Rosalba Liantonio, Pierangelo Metrangolo, Giuseppe Resnati, Rocco Ungaro and Franco Ugozzoli

      Version of Record online: 21 FEB 2006 | DOI: 10.1002/anie.200504459

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      Beauty is in the I of the beholder: Metal-ion coordination and I⋅⋅⋅I halogen bonding direct the self-assembly of achiral starting materials (a calix[4]arene tetraamide, BaI2⋅2 H2O, and 1,8-diiodoperfluorooctane) into a homochiral supramolecular complex containing double helices (see structure; Ba light purple, I purple, F green, O red, N blue, C gray; one double helix in red and yellow).

    19. Modulation of DNA Constraints That Control Macromolecular Folding (pages 1918–1921)

      Chandrasekhar V. Miduturu and Scott K. Silverman

      Version of Record online: 17 FEB 2006 | DOI: 10.1002/anie.200504124

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      Taking control with DNA: Covalently attached double-stranded DNA constraints can control the conformations of other macromolecules. A variety of approaches (including competitive ligand–aptamer interactions) were used to modulate the effects of such constraints on the structure of a large RNA molecule.

    20. Trapped Bifluoride (pages 1921–1925)

      Sung Ok Kang, Douglas Powell, Victor W. Day and Kristin Bowman-James

      Version of Record online: 21 FEB 2006 | DOI: 10.1002/anie.200504066

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      The quest is over: A tricyclic amide-based anion receptor has been synthesized by connecting two monocyclic precursors. The receptor is highly selective for the binding of the elusive bifluoride anion HF2, and the adduct represents the first structural example of an encapsulated bifluoride. The bifluoride lies midway between the two macrocycles making up the tricycle and is held by four hydrogen-bonding contacts with the macrocyclic amides.

    21. Fine Control of Red–Green–Blue Photoluminescence in Zeolites Incorporated with Rare-Earth Ions and a Photosensitizer (pages 1925–1928)

      Yuji Wada, Mutsuko Sato and Yasunori Tsukahara

      Version of Record online: 17 FEB 2006 | DOI: 10.1002/anie.200502670

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      All the colors of the rainbow can be observed upon excitation of a zeolite crystal incorporated with varying quantities of Eu3+ and Tb3+ ions as well as a sensitizer molecule (benzophenone or 4-acetylbiphenyl) in its framework structure (see picture). The colors can be fine-tuned by varying the amounts of the three components as well as the excitation wavelength and temperature.

    22. Liquid-Crystalline Quaternary Block Molecules Incorporating Bent-Core Units (pages 1928–1933)

      R. Amaranatha Reddy, Gert Dantlgraber, Ute Baumeister and Carsten Tschierske

      Version of Record online: 21 FEB 2006 | DOI: 10.1002/anie.200503402

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      A flick of a switch: The combination of fluorinated segments and oligo(dimethylsiloxane) units with bent mesogenic cores leads to new liquid-crystalline materials (see picture) that display a temperature-dependent change from ferroelectric to antiferroelectric switching. Such materials have potential use in, for example, fast-switching electrooptical microdisplays.

    23. Mechanistically Significant Details of the H/D Exchange Reactions of Propene over Acidic Zeolite Catalysts (pages 1933–1935)

      David M. Marcus, Miranda J. Hayman, Yoni M. Blau, Darryl R. Guenther, Justin O. Ehresmann, Philip W. Kletnieks and James F. Haw

      Version of Record online: 28 FEB 2006 | DOI: 10.1002/anie.200503471

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      Quid pro quo: Hydrogen–deuterium exchange of propene on solid acid catalysts was studied at 573 and 673 K with a reaction time of 3 s (see scheme). At low partial pressures and temperatures, H/D exchange produced [D5]propene as the main product. Complete deuteration ([D6]propene) was observed only at a higher temperature with the most acidic catalyst.

    24. From Solvent Fluctuations to Quantitative Redox Properties of Quinones in Methanol and Acetonitrile (pages 1936–1938)

      Joost VandeVondele, Marialore Sulpizi and Michiel Sprik

      Version of Record online: 17 FEB 2006 | DOI: 10.1002/anie.200503581

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      The effects of substituents and solvent on the redox properties of quinones were studied within the framework of Marcus theory. The relative redox potentials and reorganization energies in methanol and acetonitrile were computed with a fully atomistic method based on DFT and molecular dynamics (see model of the radical anion of benzoquinone in methanol). Hydrogen bonding contributes 0.2 eV to the reorganization energy in methanol.

    25. Rigid-Rod Metallosupramolecular Polymers of Dendronized Diazadibenzoperylene Dyes (pages 1939–1942)

      Frank Würthner, Vladimir Stepanenko and Armin Sautter

      Version of Record online: 30 JAN 2006 | DOI: 10.1002/anie.200503717

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      Second generation diazadibenzoperylene dendrimers (yellow units) undergo supramolecular polymerization with Ag+ ions (green spheres) to afford rigid-rod coordination polymers, as confirmed by atomic force microscopy studies (see image). Such cylindrical coordination polymers constitute a new class of π-conjugated materials linked by metal centers which may find application in nanoscale electronic devices.

    26. Approaching The Limit: Can One DNA Oligonucleotide Assemble into Large Nanostructures? (pages 1942–1945)

      Haipeng Liu, Yi Chen, Yu He, Alexander E. Ribbe and Chengde Mao

      Version of Record online: 15 FEB 2006 | DOI: 10.1002/anie.200504022

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      The long and the short of it: A short oligonucleotide is designed to self-assemble into micrometer-long nanotubes, which further serve as templates to fabricate metallic nanowires. This study addresses the question: what is the minimum number of DNA strands that are required for self-assembly of well-defined DNA nanostructures?

    27. Palladium-Catalyzed Allylation of Alkynes with Allyl Alcohol in Aqueous Media: Highly Regio- and Stereoselective Synthesis of 1,4-Dienes (pages 1945–1949)

      Jingmei Huang, Lei Zhou and Huanfeng Jiang

      Version of Record online: 21 FEB 2006 | DOI: 10.1002/anie.200503970

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      The direct approach: The unprecedented result of the title reaction (see scheme) is explained by a mechanism involving competition between π-allylpalladation through cleavage of the C[BOND]O bond and the insertion of an alkene. The procedure provides a highly stereo- and regioselective method to construct 1,4-dienes in an economical and environmentally benign manner.

    28. Highly Efficient Cross-Dehydrogenative-Coupling between Ethers and Active Methylene Compounds (pages 1949–1952)

      Yuhua Zhang and Chao-Jun Li

      Version of Record online: 15 FEB 2006 | DOI: 10.1002/anie.200503255

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      An unlikely couple: C[BOND]C bonds can be formed between ethers and methylene compounds by cross-dehydrogenative-coupling (see scheme; DDQ=2,3-dichloro-5,6-dicyanobenzoquinone). This straightforward reaction employs mild conditions and simple catalysts and allows reasonably high yields.

    29. Direct Catalytic Intermolecular α-Allylic Alkylation of Aldehydes by Combination of Transition-Metal and Organocatalysis (pages 1952–1956)

      Ismail Ibrahem and Armando Córdova

      Version of Record online: 6 MAR 2006 | DOI: 10.1002/anie.200504021

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      All in the same pot together: The direct catalytic α-allylic alkylation of aldehydes and cyclic ketones is achieved by using a simple, unprecedented one-pot procedure. Transition-metal and enamine catalysis are combined so that α-allylic alkylated aldehydes and cyclic ketones are formed in high yield with a direct catalytic chemo- and regioselective method.

    30. Formation of S-Shaped Disilicoicosatungstate and Efficient Baeyer–Villiger Oxidation with Hydrogen Peroxide (pages 1956–1960)

      Akihiro Yoshida, Masayuki Yoshimura, Kazuhiro Uehara, Shiro Hikichi and Noritaka Mizuno

      Version of Record online: 17 FEB 2006 | DOI: 10.1002/anie.200502543

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      Partial protonation of a divacant lacunary Keggin-type silicodecatungstate in an anhydrous organic solvent led to dehydrative condensation and formation of a novel S-shaped disilicoicosatungstate (see picture). The S-shaped cluster efficiently promotes Baeyer–Villiger oxidation of cycloalkanones with high turnover numbers (TONs, ≥1900) and high selectivities (≥90 %) for the corresponding lactones.

    31. Sequence-Specific Assignment of Aromatic Resonances of Uniformly 13C,15N-Labeled Proteins by Using 13C- and 15N-Edited NOESY Spectra (pages 1960–1963)

      Zhi Lin, Yingqi Xu, Shuai Yang and Daiwen Yang

      Version of Record online: 28 FEB 2006 | DOI: 10.1002/anie.200503558

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      NOESY neighbors: A single 3D 13C- and 15N-edited NOESY experiment can be used to assign aromatic side-chain resonance signals of 13C,15N-labeled proteins on the basis of prior assignments of the signals of backbone and aliphatic side-chain groups. This strategy will improve the precision of protein structures, especially of large proteins.

    32. Cationic State of Accessory Chlorophyll and Electron Transfer through Pheophytin to Plastoquinone in Photosystem II (pages 1964–1965)

      Hiroshi Ishikita, Jacek Biesiadka, Bernhard Loll, Wolfram Saenger and Ernst-Walter Knapp

      Version of Record online: 17 FEB 2006 | DOI: 10.1002/anie.200503804

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      It must be charged: The redox potential difference between pheophytin (PheoD1) and primary plastoquinone in the electron transfer in photosystem II from accessory chlorophyll on the D1 branch (ChlD1) is consistent with the free-energy difference estimated from kinetic studies only when computed for the cationic state equation image. YD=symmetry related redox-inactive tyrosine, YZ=redox-active tyrosine.

    33. Deantiaromatization as a Driving Force in an Electrocyclic Reaction (pages 1966–1971)

      Michael Harmata, Pinguan Zheng, Peter R. Schreiner and Armando Navarro-Vázquez

      Version of Record online: 22 FEB 2006 | DOI: 10.1002/anie.200503812

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      But how does it smell? Theory and experiment support the notion that “deantiaromatization” can serve as a driving force in the 8-π-electron electrocyclization of a cyclopentadienone (see scheme; TEA=triethylamine; TFE=trifluoroethanol). The reaction proceeds in synthetically useful yields and could be applicable to the synthesis of the antiviral agent hamigeran B.

    34. Selective Synthesis of a Trifluoromethylated Fullerene and the Crystal Structure of C60(CF3)12 (pages 1971–1974)

      Sergey I. Troyanov, Anton Dimitrov and Erhard Kemnitz

      Version of Record online: 28 FEB 2006 | DOI: 10.1002/anie.200503964

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      Unexpected selectivity: [60]Fullerene and CF3I react selectively at 440 °C to synthesize C60(CF3)12. In the product with S6 symmetry, 12 CF3 groups form a continuous loop of alternating para- and meta-C6(CF3)2 hexagons. In the crystal, the chains of molecules are strengthened owing to stacking interactions and shielding effects from the CF3 groups, thus accounting for the low volatility and solubility of the compound.

    35. Remarkable Sensitivity to DNA Base Shape in the DNA Polymerase Active Site (pages 1974–1979)

      Herman O. Sintim and Eric T. Kool

      Version of Record online: 28 FEB 2006 | DOI: 10.1002/anie.200504296

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      Shaping up: DNA polymerase I can distinguish easily and with high sensitivity between nucleobases that have the same size but differ in shape. The shape, altered through variation in the position of the halogen substituent(s), plays more of a prominent role in base-pairing efficiency and selectivity than other factors.

    36. A Highly Enantio- and Diastereoselective Cu-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with Nitroalkenes (pages 1979–1983)

      Xiao-Xia Yan, Qian Peng, Yan Zhang, Kai Zhang, Wei Hong, Xue-Long Hou and Yun-Dong Wu

      Version of Record online: 21 FEB 2006 | DOI: 10.1002/anie.200503672

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      Electronic properties of the ligands switch the diastereoselectivity in the Cu-catalyzed 1,3-dipolar cycloaddition of azomethine ylides to nitroalkenes: exo- or endo-pyrrolidines were obtained with high diastereo- and enantioselectivities in the presence of different chiral (phosphanylferrocenyl)oxazoline ligands (e.g. 3 a, b).

      Corrected by:

      Corrigendum: A Highly Enantio- and Diastereoselective Cu-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with Nitroalkenes

      Vol. 45, Issue 18, 2828, Version of Record online: 21 APR 2006

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