Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 6

February 6, 2012

Volume 51, Issue 6

Pages 1283–1488

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Corrigendum
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlights
    13. Review
    14. Communications
    15. Preview
    1. Cover Picture: Crystal Structure of Methylornithine Synthase (PylB): Insights into the Pyrrolysine Biosynthesis (Angew. Chem. Int. Ed. 6/2012) (page 1283)

      Felix Quitterer, Anja List, Priv.-Doz. Dr. Wolfgang Eisenreich, Prof. Dr. Dr. Adelbert Bacher and Prof. Dr. Michael Groll

      Version of Record online: 15 NOV 2011 | DOI: 10.1002/anie.201107547

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      The unusual amino acid pyrrolysine is found in the active site of the methylamine methyltransferases of certain methanogenic archaea. Methylornithine, an intermediate in pyrrolysine biosynthesis, is formed by the PylB-catalyzed isomerization of lysine. In their Communication on page 1339 ff., M. Groll and co-workers present the crystal structure of PylB in complex with its reaction product and suggest a fragmentation–recombination mechanism via a glycyl radical intermediate.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Corrigendum
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlights
    13. Review
    14. Communications
    15. Preview
    1. Inside Cover: Host–Guest Geometry in Pores of Zeolite ZSM-5 Spatially Resolved with Multiplex CARS Spectromicroscopy (Angew. Chem. Int. Ed. 6/2012) (page 1284)

      Dr. Katrin F. Domke, Dr. James P. R. Day, Gianluca Rago, T. Alexander Riemer, Dr. Marianne H. F. Kox, Prof. Bert M. Weckhuysen and Prof. Mischa Bonn

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/anie.201108164

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      The spatial arrangement of molecules in zeolite pores plays a crucial role in determining the overall catalytic activity of the system. In their Communication on page 1343 ff., K. F. Domke et al. give unique insight on the correlation between the geometry and reactivity of thiophene derivatives adsorbed in ZSM-5. In images obtained by coherent anti-Stokes Raman scattering (CARS) spectromicroscopy, chains of reagent molecules in the pores are resolved and the structural anisotropy of the zeolite is evident.

  3. Inside Back Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Corrigendum
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlights
    13. Review
    14. Communications
    15. Preview
    1. Inside Back Cover: Controlled Origami Folding of Hydrogel Bilayers with Sustained Reversibility for Robust Microcarriers (Angew. Chem. Int. Ed. 6/2012) (page 1489)

      Tae Soup Shim, Dr. Shin-Hyun Kim, Dr. Chul-Joon Heo, Hwan Chul Jeon and Prof. Seung-Man Yang

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/anie.201108216

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      Origami of hydrogel bilayers provides robust mircocapsules through anisotropic volume expansion. In their Communication on page 1420 ff., S.-M. Yang and co-workers show planar bilayer microparticles composed of active and passive layers that can transform into microcapsules with a closed compartment. The reversible transformation by folding and unfolding of microparticles enables in situ encapsulation and triggered release of micro- to nanoscopic encapsulants.

  4. Back Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Corrigendum
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlights
    13. Review
    14. Communications
    15. Preview
    1. Back Cover: A–T Base Pairs are More Stable Than G–C Base Pairs in a Hydrated Ionic Liquid (Angew. Chem. Int. Ed. 6/2012) (page 1490)

      Dr. Hisae Tateishi-Karimata and Prof. Dr. Naoki Sugimoto

      Version of Record online: 12 DEC 2011 | DOI: 10.1002/anie.201108253

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      Hydrated ionic liquids are “green” solvents suitable for a wide range of reactions. In their Communication on page 1416 ff., H. Tateishi-Karimata and N. Sugimoto show that A–T base pairs are more stable than G–C base pairs in choline dihydrogenphosphate because of specific interactions between the DNA bases and choline ions. Understanding the stabilities of Watson–Crick base pairs in this environmentally friendly solvent will be critical as nano-biotechnology applications of DNA advance.

  5. Graphical Abstract

    1. Top of page
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    5. Back Cover
    6. Graphical Abstract
    7. Corrigendum
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlights
    13. Review
    14. Communications
    15. Preview
  6. Corrigendum

    1. Top of page
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    5. Back Cover
    6. Graphical Abstract
    7. Corrigendum
    8. News
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    10. News
    11. Book Reviews
    12. Highlights
    13. Review
    14. Communications
    15. Preview
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      Corrigendum: Mesoporous Silica with Site-Isolated Amine and Phosphotungstic Acid Groups: A Solid Catalyst with Tunable Antagonistic Functions for One-Pot Tandem Reactions (page 1298)

      Dr. N. Raveendran Shiju, Dr. Albert H. Alberts, Dr. Syed Khalid, Prof. Dr. David R. Brown and Prof. Dr. Gadi Rothenberg

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/anie.201109094

  7. News

    1. Top of page
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    5. Back Cover
    6. Graphical Abstract
    7. Corrigendum
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlights
    13. Review
    14. Communications
    15. Preview
  8. Author Profile

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Corrigendum
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlights
    13. Review
    14. Communications
    15. Preview
    1. Michael Willis (page 1304)

      Version of Record online: 3 JAN 2012 | DOI: 10.1002/anie.201107516

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      “My favorite reaction is the Robinson synthesis of tropinone. I am waiting for the day when someone will discover the 30-hour day …” This and more about Michael Willis can be found on page 1304.

  9. News

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

    1. Top of page
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    6. Graphical Abstract
    7. Corrigendum
    8. News
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    11. Book Reviews
    12. Highlights
    13. Review
    14. Communications
    15. Preview
    1. Heterocycles in Natural Product Synthesis. Edited by Krishna C. Majumdar and Shital K. Chattopadhyay. (page 1307)

      Scott A. Snyder

      Version of Record online: 30 DEC 2011 | DOI: 10.1002/anie.201107991

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      Wiley-VCH, Weinheim, 2011. 638 pp., hardcover, € 159.00.—ISBN 978-3527327065

    2. Porous Polymers. Edited by Michael S. Silverstein, Neil R. Cameron, and Marc A. Hillmyer. (pages 1307–1308)

      Andrew Cooper

      Version of Record online: 30 DEC 2011 | DOI: 10.1002/anie.201108055

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      Wiley-VCH, Weinheim, 2011. 472 pp., hardcover, € 109.00.—ISBN 978-0470390849

  11. Highlights

    1. Top of page
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    5. Back Cover
    6. Graphical Abstract
    7. Corrigendum
    8. News
    9. Author Profile
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    11. Book Reviews
    12. Highlights
    13. Review
    14. Communications
    15. Preview
    1. Organometallic Structures

      Main-Group Metal–Alkyls: Simple Formulae but Complex Structural Chemistry (pages 1310–1311)

      Prof. William Clegg

      Version of Record online: 10 JAN 2012 | DOI: 10.1002/anie.201107519

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      Subtle differences: By using a combination of advanced crystallographic techniques and complementary computational approaches to assess the relative energies and conformational preferences, Me2Zn has been shown to form two different crystal structures. At temperatures above 180 K the methyl groups are staggered, whereas below 180 K the methyl groups are eclipsed. In contrast, the two ethyl groups in Et2Zn are shown to be mutually cis.

    2. Biotechnology

      A Fatigue-Resistant Photoswitchable Fluorescent Protein for Optical Nanoscopy (pages 1312–1314)

      Prof. Dr. G. Ulrich Nienhaus

      Version of Record online: 10 JAN 2012 | DOI: 10.1002/anie.201108036

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      Like the battery bunny: The novel photoswitchable fluorescent protein rsEGFP can be cycled between its fluorescent and nonfluorescent states more than a thousand times and is, therefore, a superb marker for high-resolution RESOLFT imaging (RESOLFT=reversible saturable optical fluorescence transition) and data storage applications.

  12. Review

    1. Top of page
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    7. Corrigendum
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    12. Highlights
    13. Review
    14. Communications
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    1. Artificial Aptamers

      Nucleic Acid and Peptide Aptamers: Fundamentals and Bioanalytical Aspects (pages 1316–1332)

      Prof. Marco Mascini, Dr. Ilaria Palchetti and Dr. Sara Tombelli

      Version of Record online: 30 DEC 2011 | DOI: 10.1002/anie.201006630

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      Antibody alternatives: This Review covers the peculiarities of the two major classes of affinity molecules produced by evolutionary approaches: nucleic acid aptamers and combinatorial non-immunoglobulin proteins (termed here, for convenience, simply peptide aptamers). The applications of these molecules in the bioanalytical field are discussed.

  13. Communications

    1. Top of page
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    6. Graphical Abstract
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    14. Communications
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    1. Alkane Activation

      Stereochemical Investigations Reveal the Mechanism of the Bacterial Activation of n-Alkanes without Oxygen (pages 1334–1338)

      René Jarling, Masih Sadeghi, Marta Drozdowska, Sven Lahme, Prof. Dr. Wolfgang Buckel, Prof. Dr. Ralf Rabus, Prof. Dr. Friedrich Widdel, Prof. Dr. Bernard T. Golding and Priv.-Doz. Dr. Heinz Wilkes

      Version of Record online: 30 NOV 2011 | DOI: 10.1002/anie.201106055

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      Anaerobic growth of the bacterium strain HxN1 with n-hexane gives nearly equal amounts of (2R,1′R)- and (2S,1′R)-(1-methylpentyl)succinate, which are formed by the radical addition of the hydrocarbon to fumarate (see scheme). The highly selective attack on the pro-S hydrogen atom at C2 of n-hexane is associated with inversion of the configuration at C2 during binding to fumarate and exhibits isotopic discrimination against a C[BOND]2H bond.

    2. Pyrrolysine Biosynthesis

      Crystal Structure of Methylornithine Synthase (PylB): Insights into the Pyrrolysine Biosynthesis (pages 1339–1342)

      Felix Quitterer, Anja List, Priv.-Doz. Dr. Wolfgang Eisenreich, Prof. Dr. Dr. Adelbert Bacher and Prof. Dr. Michael Groll

      Version of Record online: 16 NOV 2011 | DOI: 10.1002/anie.201106765

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      Made by the barrel load: The biosynthetic pathway of the recently discovered 22nd amino acid, pyrrolysine, starts with an isomerization of lysine to methylornithine, catalyzed by PylB. The X-ray crystal structure of PylB is determined (see picture) and shows it has a TIM barrel fold. The sealed central cavity contains a [4Fe-4S] cluster, S-adenosylmethionine (SAM), and methylornithine, whose 2R,3R configuration could be confirmed. The data suggest a fragmentation–recombination mechanism via a glycyl radical intermediate.

    3. Zeolite Imaging

      Host–Guest Geometry in Pores of Zeolite ZSM-5 Spatially Resolved with Multiplex CARS Spectromicroscopy (pages 1343–1347)

      Dr. Katrin F. Domke, Dr. James P. R. Day, Gianluca Rago, T. Alexander Riemer, Dr. Marianne H. F. Kox, Prof. Bert M. Weckhuysen and Prof. Mischa Bonn

      Version of Record online: 11 NOV 2011 | DOI: 10.1002/anie.201106447

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      Pore relations: Reagent molecules form head-to-tail chains in the pores of ZSM-5 zeolite particles in the presence or absence of acidic sites, according to multiplex coherent anti-Stokes Raman scattering spectromicroscopy (mCARS). The molecular ordering in the pores makes it possible to characterize the crystallographic subunits of individual ZSM-5 particles with (sub)micrometer spatial resolution in three dimensions.

    4. Kaolinite-Based Janus Particles

      Large-Scale, Low-Cost Fabrication of Janus-Type Emulsifiers by Selective Decoration of Natural Kaolinite Platelets (pages 1348–1352)

      Dunja Hirsemann, Dr. Sankaranarayanapillai Shylesh, Dr. Roger A. De Souza, Bashar Diar-Bakerly, Dr. Bernhard Biersack, Dr. David N. Mueller, Prof. Dr. Manfred Martin, Prof. Dr. Rainer Schobert and Prof. Dr. Josef Breu

      Version of Record online: 27 DEC 2011 | DOI: 10.1002/anie.201106710

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      Kaolinite platelets have inherent Janus character owing to a polar crystal structure. This character is, however, ineffective without selective modification of the two hydrophilic external basal surfaces. Amplification of the difference in the chemical nature of the surfaces is achieved by cation exchange on one side and by covalent grafting on the other. After adjustment of the surface tension, kaolinite is an effective emulsifier.

    5. Ambident Reactivity

      Ambident Reactivities of Methylhydrazines (pages 1353–1356)

      Dipl.-Chem. Tobias A. Nigst, Dipl.-Ing. Johannes Ammer and Prof. Dr. Herbert Mayr

      Version of Record online: 23 DEC 2011 | DOI: 10.1002/anie.201107315

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      Kinetics versus thermodynamics: Methyl groups increase the nucleophilic reactivity of the substituted position of hydrazines and reduce the nucleophilicity of the adjacent nitrogen center. As a result, the tertiary nitrogen atom of 1,1-dimethylhydrazine is 3000 times more reactive than the NH2 group, but under thermodynamic control substitution of an NH2 proton occurs (see picture).

    6. Iron Catalysis

      Chlorostyrenes in Iron-Catalyzed Biaryl Coupling Reactions (pages 1357–1361)

      Dipl.-Chem. Samet Gülak and Prof. Dr. Axel Jacobi von Wangelin

      Version of Record online: 27 DEC 2011 | DOI: 10.1002/anie.201106110

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      An effective protocol for iron-catalyzed biaryl syntheses by coupling chlorostyrenes with aryl Grignard reagents requires only mild reaction conditions and tolerates various functional groups. The underlying activation of deactivated aryl chlorides proceeds through a rate-determining coordination of the catalyst to the vinyl substituent and subsequent haptotropic migration along the conjugated π system to the site of C[BOND]Cl bond cleavage.

    7. Drug Design

      An Accurate Pharmacophore Mapping Method by NMR Spectroscopy (pages 1362–1365)

      Dr. Yumiko Mizukoshi, Aya Abe, Takeshi Takizawa, Dr. Hiroyuki Hanzawa, Dr. Yoshifumi Fukunishi, Prof. Dr. Ichio Shimada and Prof. Dr. Hideo Takahashi

      Version of Record online: 30 DEC 2011 | DOI: 10.1002/anie.201104905

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      Irradiation makes the difference: The relaxation-rate differences of individual ligand protons (HA, HB) between the experiment with (see picture, red) and that without (blue) saturation of the protons of the protein target reflect the proximity to the protein surface. Thus, the binding portions of ligand molecules could be identified using this “difference of inversion recovery rate with and without target irradiation” (DIRECTION) method.

    8. Ethylene Tetramerization

      A Highly Selective Ethylene Tetramerization Catalyst (pages 1366–1369)

      Yacoob Shaikh, Dr. Khalid Albahily, Matthew Sutcliffe, Valeria Fomitcheva, Prof. Dr. Sandro Gambarotta, Dr. Ilia Korobkov and Dr. Robbert Duchateau

      Version of Record online: 3 JAN 2012 | DOI: 10.1002/anie.201106517

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      Small change, big difference: The introduction of an additional CH2 group into the bridge of ligands with two P/N units leads to a different selectivity of the corresponding chromium-based catalysts. Whereas 1 produces an ethylene trimerization system, 2 provides an unprecedented ethylene tetramerization system that produces 1-octene with high purity and little or no polymer side products (see scheme; DMAO=Me3Al-depleted methylaluminoxane).

    9. Palladium Catalysis

      Palladium-Catalyzed Divergent Reactions of α-Diazocarbonyl Compounds with Allylic Esters: Construction of Quaternary Carbon Centers (pages 1370–1374)

      Dr. Zi-Sheng Chen, Dr. Xin-Hua Duan, Ping-Xin Zhou, Shaukat Ali, Jian-Yi Luo and Prof. Dr. Yong-Min Liang

      Version of Record online: 23 DEC 2011 | DOI: 10.1002/anie.201106619

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      Take two: α-Diazocarbonyl compounds display a diverse pattern of reactivity upon palladium-catalyzed reaction with esters. Esters bearing an alkynyl group on the carbonyl carbon atom lead to two different C[BOND]C bonds at the same carbon atom in a single operation through decarboxylation and migratory insertion, whereas aromatic and benzylic acid derivatives afford aromatic and benzylic esters bearing an O-substituted quaternary carbon center.

    10. Gas-Phase Conformations

      Unveiling the Shape of Aspirin in the Gas Phase (pages 1375–1378)

      Dr. Carlos Cabezas, Prof. José L. Alonso, Prof. Juan C. López and Santiago Mata

      Version of Record online: 28 DEC 2011 | DOI: 10.1002/anie.201106621

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      Accurate structural information: The first high-resolution study of isolated gas-phase acetyl salicylic acid (aspirin) is reported. Solid aspirin was vaporized by laser ablation, expanded in a supersonic jet, and characterized by Fourier transform microwave spectroscopy (see picture). Two different neutral structures have been identified from the analysis of the rotational spectrum.

    11. Suzuki–Miyaura Reactions

      The Triple Role of Fluoride Ions in Palladium-Catalyzed Suzuki–Miyaura Reactions: Unprecedented Transmetalation from [ArPdFL2] Complexes (pages 1379–1382)

      Dr. Christian Amatore, Dr. Anny Jutand and Gaëtan Le Duc

      Version of Record online: 23 DEC 2011 | DOI: 10.1002/anie.201107202

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      Fluoride ions play three roles in the Suzuki–Miyaura reaction. They favor the reaction by formation of trans-[ArPdF(PPh3)2], which reacts with Ar′B(OH)2 in an unprecedented rate-determining transmetalation, and by promoting the reductive elimination from the trans-[ArPdAr′(PPh3)2] intermediate. Conversely, F disfavors the reaction by formation of unreactive anionic Ar′B(OH)n−3Fn (n=1–3), leading to two antagonistic effects of F in the transmetalation.

    12. Catalytic Transamidation

      Transamidation of Primary Amides with Amines Using Hydroxylamine Hydrochloride as an Inorganic Catalyst (pages 1383–1386)

      C. Liana Allen, Benjamin N. Atkinson and Prof. Jonathan M. J. Williams

      Version of Record online: 30 DEC 2011 | DOI: 10.1002/anie.201107348

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      Metal-free catalysis: A method for the transamidation of primary amides with primary or secondary amines provides access to secondary and tertiary amides, by utilizing catalytic quantities of hydroxylamine hydrochloride to activate the chemically robust primary amide group (see scheme). A mechanism of primary amide activation through a hydrogen-bonding complex is proposed.

    13. Biomass Conversion

      Production of Renewable Aromatic Compounds by Catalytic Fast Pyrolysis of Lignocellulosic Biomass with Bifunctional Ga/ZSM-5 Catalysts (pages 1387–1390)

      Yu-Ting Cheng, Jungho Jae, Jian Shi, Prof. Wei Fan and Prof. George W. Huber

      Version of Record online: 27 DEC 2011 | DOI: 10.1002/anie.201107390

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      Burn, baby, burn! A new bifunctional catalyst (Ga/ZSM-5) displays increased selectivity for the production of aromatic compounds during the catalytic fast pyrolysis of biomass. With this Ga-promoted ZSM-5 catalyst, olefins such as ethylene and propylene, which are produced as intermediates, are more efficiently converted into aromatic compounds, especially benzene. Ga/ZSM-5 also promotes decarbonylation and olefin-aromatization reactions.

    14. Asymmetric Propargylation

      Brønsted Acid Catalyzed Asymmetric Propargylation of Aldehydes (pages 1391–1394)

      Pankaj Jain, Hao Wang, Prof. Dr. Kendall N. Houk and Prof. Dr. Jon C. Antilla

      Version of Record online: 28 DEC 2011 | DOI: 10.1002/anie.201107407

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      Which gets activated? A versatile and highly enantioselective chiral Brønsted acid catalyzed method for the propargylation of aldehydes is described to provide a range of chiral homopropargylic alcohols. Computational studies support the belief that the chiral phosphoric acid activates the allenyl boronic acid pinacol ester reagent rather than the aldehyde.

    15. Helical Peptides

      Induction of Unexpected Left-Handed Helicity by an N-Terminal L-Amino Acid in an Otherwise Achiral Peptide Chain (pages 1395–1399)

      Robert A. Brown, Dr. Tommaso Marcelli, Dr. Matteo De Poli, Dr. Jordi Solà and Prof. Jonathan Clayden

      Version of Record online: 3 JAN 2012 | DOI: 10.1002/anie.201107583

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      Peptide helices containing L-amino acids are typically right-handed. Exceptions are peptide helices containing the achiral amino acids 2-aminoisobutyric acid and glycine with a single chiral amino acid at the N terminus. These helices are left-handed when the N-terminal residue is a common tertiary proteinogenic amino acid, such as L-valine (see picture, left), but right-handed when the N-terminal residue is the quaternary amino acid L-α-methylvaline (right).

    16. Enamide Synthesis

      Direct Titanium-Mediated Conversion of Ketones into Enamides with Ammonia and Acetic Anhydride (pages 1400–1404)

      Dr. Jonathan T. Reeves, Zhulin Tan, Dr. Zhengxu S. Han, Dr. Guisheng Li, Dr. Yongda Zhang, Yibo Xu, Dr. Diana C. Reeves, Dr. Nina C. Gonnella, Dr. Shengli Ma, Dr. Heewon Lee, Dr. Bruce Z. Lu and Dr. Chris H. Senanayake

      Version of Record online: 3 JAN 2012 | DOI: 10.1002/anie.201107601

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      A one-step conversion of ketones into N-acetyl enamides was developed. The process employs safe and inexpensive reagents, proceeds under mild conditions, and tolerates diverse functional groups. The addition of edte (N,N,N′,N′-tetrakis(2-hydroxyethyl)ethylenediamine) prior to workup enables water solubilization of Ti alkoxides and allows a simple extractive workup.

    17. Allylic Amination

      Gold(I)-Catalyzed Enantioselective Intramolecular Dehydrative Amination of Allylic Alcohols with Carbamates (pages 1405–1407)

      Paramita Mukherjee and Prof. Ross A. Widenhoefer

      Version of Record online: 3 JAN 2012 | DOI: 10.1002/anie.201107877

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      Aliphatic nitrogen heterocycles—either five- or six-membered—are formed in high yield and with up to 94 % ee when a 1:2 mixture of [(S)-2](AuCl)2 and AgClO4 is used as the catalyst for the title reaction.

    18. NHC Ligands

      Reversible Insertion of 1,3-Di-tert-butylimidazol-2-ylidene into a Ru[BOND]H Bond and Bimetallic Activation of a N[BOND]C Bond of Imidazoline (pages 1408–1411)

      Atsushi Kaiho and Prof. Hiroharu Suzuki

      Version of Record online: 30 DEC 2011 | DOI: 10.1002/anie.201107889

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      Reversible insertion of NHC: 1,3-Di-tert-butylimidazol-2-ylidene was inserted into a ruthenium–hydride bond of [Cp*Ru(μ-H)4RuCp*] to form a 4-imidazoline complex that underwent a dynamic process, namely 1,3-migratory pendulum motion of the 4-imidazoline ligand (see scheme). Bimetallic-system-assisted N[BOND]C bond cleavage of the imidazoline ligand proceeded to generate a pseudo-diazaruthenacycle.

    19. Metal–Organic Frameworks

      Enhanced Binding Affinity, Remarkable Selectivity, and High Capacity of CO2 by Dual Functionalization of a rht-Type Metal–Organic Framework (pages 1412–1415)

      Dr. Baiyan Li, Zhijuan Zhang, Dr. Yi Li, Kexin Yao, Yihan Zhu, Zhiyong Deng, Fen Yang, Xiaojing Zhou, Dr. Guanghua Li, Haohan Wu, Nour Nijem, Prof. Dr. Yves J. Chabal, Prof. Dr. Zhiping Lai, Prof. Dr. Yu Han, Prof. Dr. Zhan Shi, Prof. Dr. Shouhua Feng and Prof. Dr. Jing Li

      Version of Record online: 23 DEC 2011 | DOI: 10.1002/anie.201105966

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      Open and friendly: The smallest member of the rht-type metal–organic frameworks (MOFs, see picture) constructed by a hexacarboxylate ligand with a nitrogen-rich imino triazine backbone shows a significantly enhanced gas binding affinity relative to all other isoreticular rht-type MOFs. The high adsorption capacity and remarkable selectivity of CO2 are attributed to the high density of open metal and Lewis basic sites in the framework.

    20. Stability of DNA

      A–T Base Pairs are More Stable Than G–C Base Pairs in a Hydrated Ionic Liquid (pages 1416–1419)

      Dr. Hisae Tateishi-Karimata and Prof. Dr. Naoki Sugimoto

      Version of Record online: 13 DEC 2011 | DOI: 10.1002/anie.201106423

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      A green solvent: Quantitative thermodynamic analyses shows that A–T base pairs are more stable than G–C base pairs in the hydrated ionic-liquid choline dihydrogenphosphate because of specific interactions between DNA bases and choline ions.

    21. Microcapsules

      Controlled Origami Folding of Hydrogel Bilayers with Sustained Reversibility for Robust Microcarriers (pages 1420–1423)

      Tae Soup Shim, Dr. Shin-Hyun Kim, Dr. Chul-Joon Heo, Hwan Chul Jeon and Prof. Seung-Man Yang

      Version of Record online: 21 NOV 2011 | DOI: 10.1002/anie.201106723

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      Soft origami structures: Planar bilayer microparticles consisting of active and passive layers show a structural transformation to microcapsules because of an anisotropic volume expansion (see picture). The soft hydrogel materials used for both layers facilitate the reversible transformation and complete closure of the compartment, which enables in situ encapsulation and triggered release of micro- to nanoscopic active ingredients.

    22. Nanoparticles

      Direct Preparation of Sulfide Semiconductor Nanoparticles from the Corresponding Bulk Powders in an Ionic Liquid (pages 1424–1427)

      Borja Rodríguez-Cabo, Dr. Eva Rodil, Dr. Héctor Rodríguez, Prof. Ana Soto and Prof. Alberto Arce

      Version of Record online: 23 DEC 2011 | DOI: 10.1002/anie.201106546

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      Just add liquid and stir: Dispersions of metal sulfide nanoparticles (CdS, ZnS, PbS, and MnS) can be prepared directly by mixing the corresponding bulk solid with an appropriate ionic liquid, without further additives or solvents (see scheme). The selection of the ionic liquid is critical for the viability of this nanoparticle preparation method.

    23. Fluid Catalytic Cracking

      Integrated Laser and Electron Microscopy Correlates Structure of Fluid Catalytic Cracking Particles to Brønsted Acidity (pages 1428–1431)

      Matthia A. Karreman, Inge L. C. Buurmans, Prof. Dr. John W. Geus, Dr. Alexandra V. Agronskaia, Dr. Javier Ruiz-Martínez, Prof. Dr. Hans C. Gerritsen and Prof. Dr. Bert M. Weckhuysen

      Version of Record online: 23 DEC 2011 | DOI: 10.1002/anie.201106651

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      Cracking the crackers: Integrated laser and electron microscopy was applied to study individual fluid catalytic cracking catalyst particles (see picture) deactivated according to an industrially relevant protocol. New insights have been obtained by correlating Brønsted acidity changes, visualized using fluorescence microscopy, with structural transformations in the zeolite and matrix components, as observed with electron microscopy.

    24. Metabolites

      Selenenylsulfide-Linked Homogeneous Glycopeptides and Glycoproteins: Synthesis of Human “Hepatic Se Metabolite A” (pages 1432–1436)

      Dr. Omar Boutureira, Dr. Gonçalo J. L. Bernardes, Dr. Marta Fernández-González, Dr. Daniel C. Anthony and Prof. Benjamin G. Davis

      Version of Record online: 30 DEC 2011 | DOI: 10.1002/anie.201106658

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      Introducing selenium: The synthesis and full characterization of human hepatic Se metabolite A has been accomplished by using a robust, efficient, and Cys-specific selenenylation protocol (see scheme; NaPi=sodium phosphate). The selenenylsulfide linkage is sufficiently stable to allow quantification of Se-containing glycoconjugates in biological fluids by using atomic detection methods.

    25. Imaging Agents

      A High-Performance Ytterbium-Based Nanoparticulate Contrast Agent for In Vivo X-Ray Computed Tomography Imaging (pages 1437–1442)

      Yanlan Liu, Kelong Ai, Jianhua Liu, Prof. Qinghai Yuan, Yangyang He and Prof. Lehui Lu

      Version of Record online: 30 DEC 2011 | DOI: 10.1002/anie.201106686

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      Enlightening particles: A contrast agent for in vivo X-ray computed tomography (CT) imaging is composed of an Yb-based nanoparticle (NP) that is stabilized with oleic acid and modified with the biocompatible polymer DSPE-PEG 2000 (see picture). The contrast agent exhibits long circulation time in vivo and low toxicity and is also much more effective than a clinical iodinated agent.

    26. Catenanes

      Templated Dynamic Synthesis of a [3]Catenane (pages 1443–1447)

      Fabien B. L. Cougnon, Nicholas A. Jenkins, Dr. G. Dan Pantoş and Prof. Jeremy K. M. Sanders

      Version of Record online: 30 DEC 2011 | DOI: 10.1002/anie.201106885

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      Three rings: The self-assembly of a water-soluble [3]catenane from a library composed of two linear building blocks, both terminated by cysteine components, is promoted either by a high salt concentration or by the presence of spermine. The spermine-templated synthesis of the [3]catenane shows that such structures can exhibit strong binding interactions with a biologically relevant target in water under near-physiological conditions.

    27. Imaging Agents

      Deep-Tissue Photoacoustic Tomography of a Genetically Encoded Near-Infrared Fluorescent Probe (pages 1448–1451)

      Dr. Grigory S. Filonov, Arie Krumholz, Dr. Jun Xia, Junjie Yao, Dr. Lihong V. Wang and Dr. Vladislav V. Verkhusha

      Version of Record online: 23 DEC 2011 | DOI: 10.1002/anie.201107026

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      Skin-deep: The combination of a near-infrared fluorescent protein (iRFP) and deep-tissue photoacoustic tomography clearly demonstrates the superiority of iRFP over other genetically encoded probes. Impressive resolution (280 μm lateral and 75 μm axial) was obtained at a depth of 4 mm in a live animal, and volumetric images of a tumor were produced (see image), thus allowing the spatially resolved monitoring of its development.

    28. Molecular Capsules

      Controlling the Self-Assembly of Metal-Seamed Organic Nanocapsules (pages 1452–1454)

      Dr. Harshita Kumari, Andrew V. Mossine, Dr. Steven R. Kline, Dr. Cindi L. Dennis, Dr. Drew A. Fowler, Dr. Simon J. Teat, Dr. Charles L. Barnes, Prof. Carol A. Deakyne and Prof. Jerry L. Atwood

      Version of Record online: 3 JAN 2012 | DOI: 10.1002/anie.201107182

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      Thermodynamic versus kinetic control: Small-angle neutron scattering (SANS) and single-crystal X-ray diffraction data have been used to elucidate the effect of temperature, solvent, and metal identity on the formation of dimeric or hexameric metal-seamed pyrogallol[4]arene capsules. Higher temperatures, methanol solution, and the use of nickel metal favor dimer formation (see scheme).

    29. C[BOND]H Activation

      Linking Ion and Neutral Chemistry in C[BOND]H Bond Electrophilic Activation: Generation and Detection of HO2. Reactive Radicals in the Gas Phase (pages 1455–1458)

      Prof. Dr. Giulia de Petris, Dr. Giancarlo Angelini, Dr. Ornella Ursini, Prof. Dr. Marzio Rosi and Dr. Anna Troiani

      Version of Record online: 23 DEC 2011 | DOI: 10.1002/anie.201107224

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      The flip side: Both the charged and uncharged products formed by C[BOND]H bond electrophilic activation have been experimentally detected in the gas phase. The HO2. radical is formed by a process involving the prototypical oxygen-centered radical cation O2.+ and the methane derivative CH2F2.

    30. Mesoporous Materials

      Conversion of Sb2Te3 Hexagonal Nanoplates into Three-Dimensional Porous Single-Crystal-Like Network-Structured Te Plates Using Oxygen and Tartaric Acid (pages 1459–1463)

      Hua Zhang, Huan Wang, You Xu, Sifei Zhuo, Yifu Yu and Prof. Dr. Bin Zhang

      Version of Record online: 3 JAN 2012 | DOI: 10.1002/anie.201107460

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      Pore genius: Sb2Te3 hexagonal nanoplates can be transformed into 3D porous network-structured Te plates by the dissolution of Sb3+ ions induced by tartaric acid (TA), the O2-assisted oxidation of Te2− ions to Te0, and a subsequent Ostwald ripening process (see picture). These Te plates can be adopted as templates for the synthesis of 3D porous nanothread-based (or nanotube-based) metal and metal telluride nanoplates.

    31. Stereochemistry

      Nonlinear Enhancement of Chiroptical Response through Subcomponent Substitution in M4L6 Cages (pages 1464–1468)

      Dr. Naoki Ousaka, Dr. Jack K. Clegg and Dr. Jonathan R. Nitschke

      Version of Record online: 30 DEC 2011 | DOI: 10.1002/anie.201107532

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      One for all, all for one: A self-assembled M4L6 cage, incorporating small amounts of enantiopure subcomponents at the peripheries, forms predominantly with a one-handed twist at all metal centers. Strong stereochemical coupling between metal centers in the cage amplifies energy differences between the ΔΔΔΔ and ΛΛΛΛ diastereomers as compared to analogous mononuclear metal complexes (see picture; red and gray bars denote chiral and achiral subcomponents, respectively).

    32. Coordination Chemistry

      Crystallographic Snapshots of the Bond-Breaking Isomerization Reactions Involving Nickel(II) Complexes with Hemilabile Ligands (pages 1469–1472)

      Charles W. Machan, Alejo M. Lifschitz, Charlotte L. Stern, Dr. Amy A. Sarjeant and Prof. Dr. Chad A. Mirkin

      Version of Record online: 23 DEC 2011 | DOI: 10.1002/anie.201107620

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      Freeze-frame: Octahedral and square-planar structural isomers, representing the two “end states” in a hemilabile ligand bond-breaking isomerization reaction, have been characterized in solution by spectroscopic methods and in the solid state by X-ray crystallography (see picture: Ni green, C gray, P orange, N blue, S yellow).

    33. Supramolecular Polymers

      Supramolecular Polymerization Triggered by Molecular Recognition between Bisporphyrin and Trinitrofluorenone (pages 1473–1476)

      Prof. Dr. Takeharu Haino, Akihide Watanabe, Takehiro Hirao and Dr. Toshiaki Ikeda

      Version of Record online: 3 JAN 2012 | DOI: 10.1002/anie.201107655

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      Networking: A bisporphyrin compound possessing an electron-deficient guest moiety assembles in a head-to-tail manner to form polymeric aggregates. Diffusion-ordered NMR spectroscopy and viscosity measurements of the aggregates confirmed the formation of sizable supramolecular polymers. Widely spread nanonetworks (see picture) are formed in solid state.

    34. Dicarbon

      Lewis Base Stabilized Dicarbon: Predictions from Theory (pages 1477–1480)

      Dr. Jason L. Dutton and Dr. David J. D. Wilson

      Version of Record online: 3 JAN 2012 | DOI: 10.1002/anie.201107815

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      New C-based ligands? Inspired by recent work on main group allotropes, a theoretical examination of Lewis base (NHC, phosphine) stabilized dicarbon has been carried out. The results indicate that the phosphine and NHC adducts of C2 have significantly different electronic structures and that both types of molecules should be powerful, bifunctional carbon-based ligands.

    35. Protein Topology

      Design, Total Chemical Synthesis, and X-Ray Structure of a Protein Having a Novel Linear-Loop Polypeptide Chain Topology (pages 1481–1486)

      Kalyaneswar Mandal, Brad L. Pentelute, Duhee Bang, Zachary P. Gates, Vladimir Yu. Torbeev and Prof. Stephen B. H. Kent

      Version of Record online: 30 DEC 2011 | DOI: 10.1002/anie.201107846

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      Lassoed at the other end: Original synthetic and structure determination methods were used to make a protein molecule with an unprecedented linear-loop polypeptide chain topology, and to characterize its X-ray structure.

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