Angewandte Chemie International Edition

Cover image for Vol. 47 Issue 15

March 31, 2008

Volume 47, Issue 15

Pages 2709–2891

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
    11. Preview
    1. Cover Picture: Exogenous Agents that Target Transmembrane Domains of Proteins (Angew. Chem. Int. Ed. 15/2008) (page 2709)

      Hang Yin

      Version of Record online: 20 MAR 2008 | DOI: 10.1002/anie.200890062

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      Molecular recognition in protein transmembrane domains is little understood because of the lack of suitable probes with high affinity and specificity. The recent development of exogenous agents that can recognize protein transmembrane domains are described by H. Yin in the Minireview on page 2744 ff. The cover picture is an artist's representation of a computed helical anti-membrane protein (CHAMP) peptide associating with a transmembrane domain of integrin αIIbβ3. These studies have laid the groundwork for targeting protein–protein interactions in the membrane. (Original artwork: Barbara Seymour.)

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
    11. Preview
    1. Inside Cover: Metal–Oxygen Isopolyhedra Assembled into Fullerene Topologies (Angew. Chem. Int. Ed. 15/2008) (page 2710)

      Tori Z. Forbes, J. Gregory McAlpin, Rachel Murphy and Peter C. Burns

      Version of Record online: 20 MAR 2008 | DOI: 10.1002/anie.200890063

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      Metal–oxygen cage clusters with fullerene topologies can be assembled from uranyl hexagonal bipyramids under certain conditions, as described by P. C. Burns and co-workers in their Communication on page 2824 ff. A cluster containing 50 polyhedra has the same topology as the fullerene C50Cl10. Synthesis of a cluster containing 40 uranyl hexagonal bipyramids demonstrates that the inclusion of topological squares in addition to pentagons and hexagons gives access to topological isomers that are not possible for carbon fullerenes.

  3. Graphical Abstract

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

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

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
    11. Preview
    1. Expanding the Synthetic Potential of Asymmetric Deprotonation: Arylation of Carbanions (pages 2734–2736)

      Peter O'Brien and Julia L. Bilke

      Version of Record online: 10 MAR 2008 | DOI: 10.1002/anie.200704539

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      Aryl unplugged: Two conceptually new disconnections are equivalent to arylation of enantioenriched carbanions obtained by asymmetric deprotonation. One retrosynthesis (see scheme, above) involves N-Boc pyrrolidine (Boc=tert-butoxycarbonyl, Ar=aryl) and an organozinc intermediate, and the other (below) O-alkyl carbamates with organoboron intermediates.

    2. The Groves–Spiro Dioxomanganese(V) Story (pages 2737–2739)

      Zeev Gross

      Version of Record online: 10 MAR 2008 | DOI: 10.1002/anie.200705750

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      Double O agents: The first definitive spectroscopic evidence for trans-dioxomanganese(V) porphyrins (see picture) has been reported by Groves, Spiro, and co-workers. Their work extends the scope of oxo-coordination chemistry and opens the way for the exploration of reactivity patterns of trans-dioxo complexes of first-row transition-metal ions.

    3. Selective Oxidation of Aliphatic C[BOND]H Bonds in the Synthesis of Complex Molecules (pages 2740–2742)

      Mathias Christmann

      Version of Record online: 17 MAR 2008 | DOI: 10.1002/anie.200705766

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      Tamed cat: Iron-catalyzed selective C[BOND]H oxidation reactions present new possibilities in the synthesis and modification of natural products. As a model reaction of a possible C[BOND]H oxidation as part of a total synthesis, the natural product (+)-artemisinin was converted into (+)-10β-hydroxyartemisinin in 34 % yield (see scheme). The combination of nontoxic metal catalyst with H2O2 is an environmentally friendly process.

  7. Minireview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
    11. Preview
    1. Exogenous Agents that Target Transmembrane Domains of Proteins (pages 2744–2752)

      Hang Yin

      Version of Record online: 3 MAR 2008 | DOI: 10.1002/anie.200704780

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      Over the limit: Despite accounting for about one third of all proteins encoded in the human genome, the functions and structures of the transmembrane domains of membrane proteins are poorly understood. Major advances have recently been made in the development of exogenous agents that can recognize these domains, which have laid the groundwork for targeting protein–protein interactions in the membrane bilayers (see picture).

  8. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
    11. Preview
    1. Transmission and Amplification of Information and Properties in Nanostructured Liquid Crystals (pages 2754–2787)

      John W. Goodby, Isabel M. Saez, Stephen J. Cowling, Verena Görtz, Michael Draper, Alan W. Hall, Susan Sia, Guirac Cosquer, Seung-Eun Lee and E. Peter Raynes

      Version of Record online: 29 FEB 2008 | DOI: 10.1002/anie.200701111

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      Tune in your crystal set: Design of molecular shape, deformable molecular topologies, self-assembly, and self-organization combine together to yield super- and supramolecular liquid crystals (such as the nanomolecular “Boojum” shown in the picture) that are capable of exhibiting “superphases”. Transmission and amplification of physical properties are often observed for such systems.

  9. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Minireview
    9. Review
    10. Communications
    11. Preview
    1. Direct Imaging of the MoVTeNbO M1 Phase Using An Aberration-Corrected High-Resolution Scanning Transmission Electron Microscope (pages 2788–2791)

      William D. Pyrz, Douglas A. Blom, Thomas Vogt and Douglas J. Buttrey

      Version of Record online: 7 MAR 2008 | DOI: 10.1002/anie.200705700

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      Seeing is believing: Aberration-corrected STEM imaging allows direct visualization of the orthorhombic M1 phase primary component of the MoVNbTeO propane ammoxidation catalyst. Atomic coordinates and site occupancies are obtained, and the beam-sensitive Te chains in the hexagonal and heptagonal channels are successfully imaged. These results suggest that HR-HAADF imaging may provide improved starting models for Rietveld analysis of complex structures.

    2. Direct Visualization of Oxygen Distribution in Operating Fuel Cells (pages 2792–2795)

      Junji Inukai, Kenji Miyatake, Kenji Takada, Masahiro Watanabe, Tsuyoshi Hyakutake, Hiroyuki Nishide, Yuzo Nagumo, Masayuki Watanabe, Makoto Aoki and Hiroshi Takano

      Version of Record online: 5 MAR 2008 | DOI: 10.1002/anie.200705516

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      Cell diagnosis: The oxygen distribution in the interior of operating fuel cells can be visualized by using dye films painted on the transparent gas flow field (see image). The spatial and time resolutions are 300 μm and 500 ms, respectively. The oxygen distribution in a polymer electrolyte membrane fuel cell was not in accordance with that expected from the current, suggesting a significant contribution from water.

    3. Synthesis and Structural Characterization of C70H38 (pages 2796–2799)

      Thomas Wågberg, Mattias Hedenström, Alexandr V. Talyzin, Ingmar Sethson, Yury O. Tsybin, Jeremiah M. Purcell, Alan G. Marshall, Dag Noréus and Dan Johnels

      Version of Record online: 28 FEB 2008 | DOI: 10.1002/anie.200705450

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      Feeling the pressure: Hydrogenation of C70 at 100 bar H2 pressure and 400 °C for 72 h has enabled isolation of C70H38. Full structural assignment was achieved by 2D NMR spectroscopic studies, which show C70H38 to have C2 symmetry and contain five benzenoid rings and two protonated carbon atoms on the equator (see picture). The proposed protonation scheme for the formation of this isomer shows a high similarity to reported C70F38isomers.

    4. Macroscopically Ordered Polymer/CaCO3 Hybrids Prepared by Using a Liquid-Crystalline Template (pages 2800–2803)

      Tatsuya Nishimura, Takahiro Ito, Yuya Yamamoto, Masafumi Yoshio and Takashi Kato

      Version of Record online: 28 FEB 2008 | DOI: 10.1002/anie.200705062

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      Unidirectionally aligned hybrids consisting of chitin and calcite were obtained by template crystallization of CaCO3 in an ordered chitin film with nematic liquid-crystalline molecular alignment. The picture shows the resulting chitin matrix containing CaCO3 rods, schematically and in the form of an optical micrograph, and the selected-area electron diffraction pattern of a thin section of a single rod.

    5. A Near-Infrared-Fluorescence-Quenched Gold-Nanoparticle Imaging Probe for In Vivo Drug Screening and Protease Activity Determination (pages 2804–2807)

      Seulki Lee, Eui-Joon Cha, Kyeongsoon Park, Seung-Young Lee, Jin-Ki Hong, In-Cheol Sun, Sang Yoon Kim, Kuiwon Choi, Ick Chan Kwon, Kwangmeyung Kim and Cheol-Hee Ahn

      Version of Record online: 27 FEB 2008 | DOI: 10.1002/anie.200705240

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      Nanodiagnosis: A matrix-metalloproteinase (MMP) sensitive gold-nanoparticle (AuNP) imaging probe quenches conjugated near-infrared (NIR) dyes with high efficiency and is specifically activated by the target MMPs (see picture, left). With this system, nanomolar amounts of protease can be detected—both in vitro and in vivo. Experiments disclose an apparent positive contrast in MMPs-positive tumor-bearing mice (right).

    6. Anti-MRSA Agent Discovery Using Diversity-Oriented Synthesis (pages 2808–2812)

      Gemma L. Thomas, Richard J. Spandl, Freija G. Glansdorp, Martin Welch, Andreas Bender, Joshua Cockfield, Jodi A. Lindsay, Clare Bryant, Derek F. J. Brown, Olivier Loiseleur, Hélène Rudyk, Mark Ladlow and David R. Spring

      Version of Record online: 28 FEB 2008 | DOI: 10.1002/anie.200705415

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      Beating the superbugs: Diversity-oriented synthesis using a solid-supported phosphonate unit to synthesize 242 drug-like compounds based on 18 natural-product-like scaffolds led to the discovery of gemmacin (see scheme). This new structural class of antibiotic is active towards methicillin-resistant Staphylococcus aureus (MRSA).

    7. Photoactivation of Silver-Exchanged Zeolite A (pages 2813–2816)

      Gert De Cremer, Yasuko Antoku, Maarten B. J. Roeffaers, Michel Sliwa, Jasper Van Noyen, Steve Smout, Johan Hofkens, Dirk E. De Vos, Bert F. Sels and Tom Vosch

      Version of Record online: 28 FEB 2008 | DOI: 10.1002/anie.200704861

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      The right bright light: Silver-exchanged zeolite 3A crystals show remarkable luminescent properties. Upon irradiation with high-power UV light, a strong photoactivation process takes place which results in an emission increase of up to two orders of magnitude (see picture). The crystals of interest—or even small domains within one crystal—can be selectively activated by using a confocal microscope.

    8. Tuning the Decomposition Temperature in Complex Hydrides: Synthesis of a Mixed Alkali Metal Borohydride (pages 2817–2819)

      E. Anne Nickels, Martin Owen Jones, William I. F. David, Simon R. Johnson, Rebecca L. Lowton, Marco Sommariva and Peter P. Edwards

      Version of Record online: 28 FEB 2008 | DOI: 10.1002/anie.200704949

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      Variegated decomposers: The synthesis of the first mixed alkali metal borohydride, which contains lithium and potassium, is presented. LiK(BH4)2 (see picture; K crimson, Li yellow, B green, H gray) has a crystal structure similar to LiBH4, and a thermal decomposition temperature between those of LiBH4 and KBH4. Using this route, the hydrogen desorption thermodynamics of complex hydrides can be easily tailored.

    9. Kinetics of Iminium Ion Catalysis (pages 2820–2823)

      Gareth Evans, Timothy J. K. Gibbs, Robert L. Jenkins, Simon J. Coles, Michael B. Hursthouse, James A. Platts and Nicholas C. O. Tomkinson

      Version of Record online: 29 FEB 2008 | DOI: 10.1002/anie.200705539

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      Identifying the bottleneck: Kinetic and computational data for the key steps of the iminium ion catalyzed Diels–Alder reaction show that the cycloaddition (step II in scheme) is the rate-determining step of the catalytic cycle and provide a rationale for developing more-active catalyst architectures.

    10. Metal–Oxygen Isopolyhedra Assembled into Fullerene Topologies (pages 2824–2827)

      Tori Z. Forbes, J. Gregory McAlpin, Rachel Murphy and Peter C. Burns

      Version of Record online: 13 FEB 2008 | DOI: 10.1002/anie.200705563

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      Conditions that permit the assembly of metal–oxygen isopolyhedra into fullerene topologies favor the hexagonal bipyramid as the basic building unit. Uranyl hexagonal bipyramids containing two peroxide edges have been used to create a cage cluster with a fullerene topology containing 50 polyhedra (see picture), as well as cage cluster of 40 polyhedra that contains topological squares, pentagons, and hexagons.

    11. [Mn6] under Pressure: A Combined Crystallographic and Magnetic Study (pages 2828–2831)

      Alessandro Prescimone, Constantinos J. Milios, Stephen Moggach, John E. Warren, Alistair R. Lennie, Javier Sanchez-Benitez, Konstantin Kamenev, Roland Bircher, Mark Murrie, Simon Parsons and Euan K. Brechin

      Version of Record online: 5 MAR 2008 | DOI: 10.1002/anie.200705819

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      Folding under pressure: High-pressure crystallography of an Mn6 single-molecule magnet reveals dramatic changes in the intramolecular geometry of the magnetic core (see picture; Mn purple, O red, N blue). These structural changes effect the magnetic properties of the molecule: the magnitude of the ferromagnetic exchange between the metals is decreased, and under extreme pressure switches to antiferromagnetic.

    12. A Photoinducible 1,3-Dipolar Cycloaddition Reaction for Rapid, Selective Modification of Tetrazole-Containing Proteins (pages 2832–2835)

      Wenjiao Song, Yizhong Wang, Jun Qu, Michael M. Madden and Qing Lin

      Version of Record online: 29 FEB 2008 | DOI: 10.1002/anie.200705805

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      Reactive but biologically inert: The bioorthogonal title reaction enables highly specific chemical modifications, such as lipidation, of engineered proteins containing a diphenyltetrazole group (see scheme). The cycloaddition in biological media is extremely fast (≤1 min) and tolerant of proteinaceous groups. Strongly fluorescent pyrazoline cycloadducts are generated with simple alkenes.

    13. Room Temperature Copper-Catalyzed 2-Functionalization of Pyrrole Rings by a Three-Component Coupling Reaction (pages 2836–2839)

      Seung Hwan Cho and Sukbok Chang

      Version of Record online: 3 MAR 2008 | DOI: 10.1002/anie.200705940

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      Making rings: A new Cu-catalyzed three-component coupling reaction between 1-alkynes, sulfonyl azides, and pyrrole derivatives has been developed for making 2-functionalized pyrrole rings (see scheme). This C[BOND]C bond formation offers high efficiency and selectivity, mild reaction conditions, and a wide substrate scope.

    14. Chiral Brønsted Acid Catalyzed Asymmetric Baeyer–Villiger Reaction of 3-Substituted Cyclobutanones by Using Aqueous H2O2 (pages 2840–2843)

      Senmiao Xu, Zheng Wang, Xue Zhang, Xumu Zhang and Kuiling Ding

      Version of Record online: 5 MAR 2008 | DOI: 10.1002/anie.200705932

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      A catalytic amount of a chiral Brønsted acid with aqueous H2O2 as the oxidant is sufficient for the enantioselective Baeyer–Villiger oxidation of 3-substituted cyclobutanones to give the corresponding γ-lactones in excellent yields and up to 93 % ee. The method employs benign aqueous H2O2 instead of stoichiometric amounts of a dangerous peracid.

    15. Total Synthesis and Structure Assignment of Papuamide B, A Potent Marine Cyclodepsipeptide with Anti-HIV Properties (pages 2844–2848)

      Weiqing Xie, Derong Ding, Weiwei Zi, Guangyu Li and Dawei Ma

      Version of Record online: 3 MAR 2008 | DOI: 10.1002/anie.200705557

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      Synthesis in stereo: The first total synthesis of papuamide B, a cyclic peptide isolated from a marine sponge, has been achieved. The configuration of three stereogenic centers of its dienoic acid unit has been established by comparison to a series of stereoisomers of known configuration, and the stereochemistry of its 2,3-diaminobutanoic acid segment has been revised.

    16. Highly Efficient Organic Reactions “on Water”, “in Water”, and Both (pages 2849–2852)

      Nelly Shapiro and Arkadi Vigalok

      Version of Record online: 3 MAR 2008 | DOI: 10.1002/anie.200705347

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      Wet, wet, wet: Hydrophobic aldehydes are cleanly oxidized upon stirring with water in air. Addition of hydrophobic isocyanides to aqueous suspensions of such aldehydes results in the formation of Passerini reaction products, with the aldehyde being the source of both carbonyl and ester functions. Partially water-soluble reagents reacted slower than water-insoluble ones. Isotope labeling studies show that water participates in these “on water” reactions.

    17. Sequence-Based Design of α/β-Peptide Foldamers That Mimic BH3 Domains (pages 2853–2856)

      W. Seth Horne, Melissa D. Boersma, Matthew A. Windsor and Samuel H. Gellman

      Version of Record online: 10 MAR 2008 | DOI: 10.1002/anie.200705315

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      Into the fold: Foldamers have emerged as versatile scaffolds for the design of functional macromolecules. A straightforward design principle based on primary sequence can be used to convert an α-peptide ligand derived from a natural protein-binding domain into an α/β-peptide with comparable binding affinity for protein targets bound by the α-peptide (see scheme).

    18. Synthesis and Structure of Eight-, Nine-, and Ten-Membered Rings with P-Se-Se-P Linkages (pages 2857–2859)

      Guoxiong Hua, Yang Li, Alexandra M. Z. Slawin and J. Derek Woollins

      Version of Record online: 3 MAR 2008 | DOI: 10.1002/anie.200705021

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      Full circle: The reaction of [PhP(Se)(μ-Se)]2 with alkyl or aryl diols affords five unusual P[BOND]Se heterocycles with eight-, nine-, and ten-membered rings containing P-Se-Se-P linkages. The structure of the ten-membered ring is shown.

    19. Ditryptophan Conjugation Triggers Conversion of Biotin Fibers into Soft Spherical Structures (pages 2860–2863)

      K. B. Joshi and Sandeep Verma

      Version of Record online: 27 FEB 2008 | DOI: 10.1002/anie.200705012

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      Trigger happy: Biotin and its methyl ester form long fibers in solution, which are transformed into soft spherical structures upon simple conjugation with ditryptophan dipeptide (see picture). Such morphogenesis is not achieved in a controlled fashion by other aromatic amino acids.

    20. S42− Rings, Disulfides, and Sulfides in Transition-Metal Complexes: The Subtle Interplay of Oxidation and Structure (pages 2864–2868)

      Carlo Mealli, Andrea Ienco, Anne Poduska and Roald Hoffmann

      Version of Record online: 10 MAR 2008 | DOI: 10.1002/anie.200705296

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      Coming together, breaking apart: A theoretical analysis of the oxidative coupling of two metal-coordinated disulfide species to a S42− rectangle provides an opening to a reexamination of a number of compounds hitherto considered to be disulfide complexes. An electronic framework helps explain how the nature of the metal controls inner redox processes and the alternative stabilization of S42− or 2 S22− (or S2−) species (see scheme).

    21. Hydride Shift Generated Oxonium Ions: Evidence for Mechanism and Intramolecular Trapping Experiments to Form trans THF Derivatives (pages 2869–2871)

      Timothy J. Donohoe, Oliver Williams and Gwydion H. Churchill

      Version of Record online: 28 FEB 2008 | DOI: 10.1002/anie.200705340

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      Switching sides: cis THF derivatives produced from the oxidative cyclization of dienes and diols can be transformed into the corresponding trans heterocycles through a 1,2-hydride shift and intramolecular trapping with a hydride nucleophile (see scheme). Moreover, organometallic compounds can be used to trap the oxonium ion generated in this way so that it is possible to introduce various groups at the C-2 position with control of stereochemistry.

    22. Pyridine-N-Oxide as a Mild Reoxidant Which Transforms Osmium-Catalyzed Oxidative Cyclization (pages 2872–2875)

      Timothy J. Donohoe, Katherine M. P. Wheelhouse (née Gosby), Peter J. Lindsay-Scott, Paul A. Glossop, Ian A. Nash and Jeremy S. Parker

      Version of Record online: 5 MAR 2008 | DOI: 10.1002/anie.200705425

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      The PNOman can: The use of pyridine-N-oxide (PNO) transforms the catalytic oxidative cyclization to include the formation of pyrrolidines from N-Z-protected amino alcohols and amino acids (see scheme; Z=PhCH2OCO). This new method expands the scope of the oxidative cyclization as illustrated with the synthesis of a range of di- and trisubstituted pyrrolidines with complete control of stereochemistry.

    23. Direct and Waste-Free Amidations and Cycloadditions by Organocatalytic Activation of Carboxylic Acids at Room Temperature (pages 2876–2879)

      Raed M. Al-Zoubi, Olivier Marion and Dennis G. Hall

      Version of Record online: 5 MAR 2008 | DOI: 10.1002/anie.200705468

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      Taming carboxylic acids: ortho-Iodo- and ortho-bromophenylboronic acids are exceptional organocatalysts in atom-economical amidations between free carboxylic acids and amines, including functionalized ones, and can also provide LUMO-lowering activation in [4+2] cycloadditions of α,β-unsaturated carboxylic acids.

    24. Iron-Catalyzed S-Arylation of Thiols with Aryl Iodides (pages 2880–2883)

      Arkaitz Correa, Mónica Carril and Carsten Bolm

      Version of Record online: 3 MAR 2008 | DOI: 10.1002/anie.200705668

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      Strike while the iron is hot: An efficient iron-catalyzed protocol for the S-arylation of aromatic and heteroaromatic thiol derivatives has been developed, which involves an inexpensive catalyst system formed by combining FeCl3 and N,N′-dimethylethylenediamine at 135 °C. This method avoids the use of expensive and/or air-sensitive ligands and provides in most cases the desired sulfide in high yields.

    25. Shape and Crystal-Plane Effects of Nanoscale Ceria on the Activity of Au-CeO2 Catalysts for the Water–Gas Shift Reaction (pages 2884–2887)

      Rui Si and Maria Flytzani-Stephanopoulos

      Version of Record online: 10 MAR 2008 | DOI: 10.1002/anie.200705828

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      A two-step synthesis method is used to prepare gold-on-ceria nanorods, nanocubes, and nanopolyhedra (see picture), and a strong shape-effect of CeO2 on the water–gas shift reaction activity of the catalysts is identified. Gold on the (110) facets of ceria nanorods shows the highest activity.

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