Angewandte Chemie International Edition

Cover image for Vol. 46 Issue 8

February 12, 2007

Volume 46, Issue 8

Pages 1189–1349

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Book Reviews
    8. Highlight
    9. Minireview
    10. Review
    11. Communications
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    1. Cover Picture: Supramolecular Aggregates of Dendritic Multishell Architectures as Universal Nanocarriers (Angew. Chem. Int. Ed. 8/2007) (page 1189)

      Michał R. Radowski, Anuj Shukla, Hans von Berlepsch, Christoph Böttcher, Guillaume Pickaert, Heinz Rehage and Rainer Haag

      Version of Record online: 5 FEB 2007 | DOI: 10.1002/anie.200790022

      Chemical chameleons is an apt description for a new class of dendritic multishell architectures that exhibit universal transport properties for a variety of guest molecules in a broad range of solvent environments. In their Communication on page 1265 ff., R. Haag and co-workers describe a supramolecular aggregation phenomenon that is responsible for the unique ability of these dendritic multishell architectures to encapsulate polar and nonpolar guests.

  2. Inside Cover

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Book Reviews
    8. Highlight
    9. Minireview
    10. Review
    11. Communications
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    1. Inside Cover Picture: Structural and Compositional Control in {M12} Cobalt and Nickel Coordination Clusters Detected Magnetochemically and with Cryospray Mass Spectrometry (Angew. Chem. Int. Ed. 8/2007) (page 1190)

      Geoffrey J. T. Cooper, Graham N. Newton, Paul Kögerler, De-Liang Long, Larry Engelhardt, Marshall Luban and Leroy Cronin

      Version of Record online: 5 FEB 2007 | DOI: 10.1002/anie.200790023

      Coordination clusters comprising three linked M4 O4 cubanes are prepared. The resulting isostructural {Ni12 } (see picture) and {Co12} cations, as well as mixed-metal structures, are characterized by ferro-and antiferromagnetic coupling. The composition of the cluster complexes was confirmed by low-temperature electrospray mass spectrometry. For more information on these species, see the Communication by P. Kögerler, L. Cronin, and co-workers on page 1340ff.

  3. Graphical Abstract

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    4. Graphical Abstract
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  4. Corrigendum

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

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

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

    1. Top of page
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    4. Graphical Abstract
    5. Corrigendum
    6. News
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    11. Communications
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    1. Carbene Chemistry: Stereoregular Polymers from Diazo Compounds (pages 1208–1210)

      Alfred F. Noels

      Version of Record online: 3 JAN 2007 | DOI: 10.1002/anie.200603660

      Thumbnail image of graphical abstract

      From carbenes to polymers: The synthesis of polymers that bear a polar group (R) on every main-chain carbon atom, while controlling their stereochemistry, was an elusive goal until quite recently, when it was reported that rhodium(I)-catalyzed polymerization of functionalized carbenes (from diazo compounds) provides access to such stereoregular polymers (see scheme).

  8. Minireview

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    1. Structures of RNA Switches: Insight into Molecular Recognition and Tertiary Structure (pages 1212–1219)

      Harald Schwalbe, Janina Buck, Boris Fürtig, Jonas Noeske and Jens Wöhnert

      Version of Record online: 17 JAN 2007 | DOI: 10.1002/anie.200604163

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      An important mode of action in gene expression is based on the highly specific and high-affinity binding of ligands to, and the resultant conformational switching of, RNA switches (riboswitches). Structures of RNA–ligand complexes give insight into the molecular recognition of small metabolites by riboswitches and into the stabilizing interactions of tertiary structures, aiding the targeted design of new high-affinity RNA-binding molecules.

  9. Review

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    1. Magnetic Nanoparticles: Synthesis, Protection, Functionalization, and Application (pages 1222–1244)

      An-Hui Lu, E. L. Salabas and Ferdi Schüth

      Version of Record online: 5 FEB 2007 | DOI: 10.1002/anie.200602866

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      Particularly attractive: Magnetic nanoparticles can be prepared and protected against corrosion in a variety of ways (Scheme: polystyrene (PS) coating of MnFe2O4 particles by atom-transfer radical polymerization). The protected magnetic nanoparticles can be further functionalized for many applications including catalysis and biotechnology.

  10. Communications

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Book Reviews
    8. Highlight
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    1. IAPP Mimic Blocks Aβ Cytotoxic Self-Assembly: Cross-Suppression of Amyloid Toxicity of Aβ and IAPP Suggests a Molecular Link between Alzheimer's Disease and Type II Diabetes (pages 1246–1252)

      Li-Mei Yan, Aleksandra Velkova, Marianna Tatarek-Nossol, Erika Andreetto and Aphrodite Kapurniotu

      Version of Record online: 4 JAN 2007 | DOI: 10.1002/anie.200604056

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      Le fabuleux destin d'amyloid disease: A peptide-derived inhibitor for amyloid diseases binds the Alzheimer's disease β-amyloid peptide (Aβ40) and the type II diabetes islet amyloid polypeptide (IAPP) and blocks cytotoxic self-assembly of both peptides. Evidence is also presented for a high-affinity interaction between Aβ40 and IAPP that results in cross-suppression of cytotoxic self-association of both peptides.

    2. Synthetic Mimetics of the CD4 Binding Site of HIV-1 gp120 for the Design of Immunogens (pages 1253–1255)

      Raimo Franke, Tatjana Hirsch, Heike Overwin and Jutta Eichler

      Version of Record online: 9 JAN 2007 | DOI: 10.1002/anie.200603274

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      Do you copy? The epitope of the broadly neutralizing anti-HIV-1 antibody mAb b12 overlaps the CD4 binding site (CD4bs) of the viral envelope glycoprotein gp120 (see picture). Synthetic mimetics of the CD4bs are therefore promising immunogen candidates to elicit a broadly neutralizing immune response. Polyclonal antisera against such a mimetic molecule specifically recognize gp120 and compete with mAb b12 for binding to gp120.

    3. Violating the Isolated Pentagon Rule (IPR): The Endohedral Non-IPR C70 Cage of Sc3N@C70 (pages 1256–1259)

      Shangfeng Yang, Alexey A. Popov and Lothar Dunsch

      Version of Record online: 9 JAN 2007 | DOI: 10.1002/anie.200603281

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      Breaking the rule: The first isolated endohedral cluster fullerene of C70 (Sc3N@C70) exhibits a cage structure that does not obey the isolated pentagon rule. It contains three pairs of adjacent pentagons, which are coordinated to the three Sc atoms of the asymmetrical Sc3N cluster (see the DFT-optimized structure; red Sc, blue N).

    4. Macrocyclic Ferrocenyl–Bisimidazoline Palladacycle Dimers as Highly Active and Enantioselective Catalysts for the Aza-Claisen Rearrangement of Z-Configured N-para-Methoxyphenyl Trifluoroacetimidates (pages 1260–1264)

      Sascha Jautze, Paul Seiler and René Peters

      Version of Record online: 9 JAN 2007 | DOI: 10.1002/anie.200603568

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      In just four steps from ferrocene, macrocyclic ferrocenyl bispalladacyles have been synthesized by using a diastereoselective biscyclopalladation reaction as the key step. The complexes not only possess a fascinating structure but are also the first highly active catalysts for the title reaction (see scheme), requiring as little as 0.1 mol % of catalyst for most of the substrates. Ts=toluene-4-sulfonyl.

    5. Supramolecular Aggregates of Dendritic Multishell Architectures as Universal Nanocarriers (pages 1265–1269)

      Michał R. Radowski, Anuj Shukla, Hans von Berlepsch, Christoph Böttcher, Guillaume Pickaert, Heinz Rehage and Rainer Haag

      Version of Record online: 5 FEB 2007 | DOI: 10.1002/anie.200603801

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      Chemical chameleons: Highly stable supramolecular aggregates built from dendritic multishell architectures show a universal transport ability for both polar and nonpolar guest molecules and can adapt to various solvent environments, ranging from toluene to water.

    6. Dibenzo[c,g]fluorene: The Combination of Cyclopentadiene and 1,1′-Binaphthyl in One Ligand (pages 1270–1273)

      Frank Pammer, Yu Sun, Claudia May, Gotthelf Wolmershäuser, Harald Kelm, Hans-Jörg Krüger and Werner R. Thiel

      Version of Record online: 5 JAN 2007 | DOI: 10.1002/anie.200604230

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      Fluorene's big brother: The first transition-metal complexes of the dibenzo[c,g]fluorenyl anion (Dbf), an intrinsically chiral derivative of the cyclopentadienyl anion, are reported (see structure of [(Dbf)Mn(CO)3]). According to density functional calculations, the electronic properties of this ligand differ significantly from those of the fluorenyl anion.

    7. Highly Enantioselective Hydrosilylation/Cyclization of 1,6-Enynes Catalyzed by Rhodium(I) Complexes of Spiro Diphosphines (pages 1275–1277)

      Bao-Min Fan, Jian-Hua Xie, Shen Li, Li-Xin Wang and Qi-Lin Zhou

      Version of Record online: 4 JAN 2007 | DOI: 10.1002/anie.200603533

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      Highly enantioselective synthesis: The rhodium(I) complex of the chiral ligand SDP is successfully used as a catalyst for the hydrosilylation/cyclization of 1,6-enynes with silanes. Under the optimized reaction conditions, optically active silylalkenes containing cyclopentane or pyrrolidine rings are obtained in good yields with excellent enantioselectivities (see scheme). DCE=1,2-dichloroethane

    8. Controlled Rotary Motion in a Monolayer of Molecular Motors (pages 1278–1280)

      Michael M. Pollard, Monika Lubomska, Petra Rudolf and Ben L. Feringa

      Version of Record online: 5 JAN 2007 | DOI: 10.1002/anie.200603618

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      All for one: The relative unidirectional rotary motion of light-driven molecular motors in solution was transformed into controlled rotary motion in a monolayer on quartz. The correlation of the CD spectroscopic behavior of the monolayer with its solution counterpart suggests that the motors retain their function when grafted to the surface.

    9. Direct ortho Iodination of β- and γ-Aryl Alkylamine Derivatives (pages 1281–1283)

      José Barluenga, Julia M. Álvarez-Gutiérrez, Alfredo Ballesteros and José M. González

      Version of Record online: 5 JAN 2007 | DOI: 10.1002/anie.200603631

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      Two in one! A trifluoroacetamide protecting group not only masks an amine functionality, but also mimics peptidyl directing effects as a controlling unit in an efficient ortho iodination of a variety of biologically relevant small molecules (see example).

    10. A Mild Chemically Cleavable Linker System for Functional Proteomic Applications (pages 1284–1286)

      Steven H. L. Verhelst, Marko Fonović and Matthew Bogyo

      Version of Record online: 5 JAN 2007 | DOI: 10.1002/anie.200603811

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      An amicable split: Small-molecule probes can be applied for the enrichment of specific protein targets from a complex proteome. A cleavable linker system, which prevents the release of unwanted, nonspecifically bound proteins, can be used for a very mild and highly selective cleavage of probe-labeled proteins.

    11. Structural Rearrangements Induced by Photoexcitation in a RbCoFe Prussian Blue Derivative (pages 1287–1289)

      Christophe Cartier dit Moulin, Guillaume Champion, Jean-Daniel Cafun, Marie-Anne Arrio and Anne Bleuzen

      Version of Record online: 9 JAN 2007 | DOI: 10.1002/anie.200603829

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      Light influence: The Co crystal-field parameter was used as a probe of the photoinduced metastable state of a RbCoFe Prussian blue analogue. From the light-induced change in this parameter, a scheme of the photoinduced structural rearrangement is proposed in which cooperative interactions within the three-dimensional structure impose linear geometry on all Co-NC-Fe entities in the metastable state (see picture).

    12. Diastereomeric Fluoroolefins as Peptide Bond Mimics Prepared by Asymmetric Reductive Amination of α-Fluoroenones (pages 1290–1292)

      Guillaume Dutheuil, Samuel Couve-Bonnaire and Xavier Pannecoucke

      Version of Record online: 5 JAN 2007 | DOI: 10.1002/anie.200604246

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      Fluoropeptidomimetics: An efficient asymmetric reductive amination of fluoroenones has been developed that affords potential precursors of fluoropeptide isosteres. Stereoselective routes with different reductive agents provided both diastereomers from the same nonracemic sulfinyl imine. The method was applied to the synthesis of different dipeptide analogues.

    13. Effective Chirality Transfer in Ionic Liquids through Ion-Pairing Effects (pages 1293–1295)

      Peter Steffen Schulz, Natalia Müller, Andreas Bösmann and Peter Wasserscheid

      Version of Record online: 9 JAN 2007 | DOI: 10.1002/anie.200604406

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      Passing it on: Since every reaction at a prochiral ion must take place in close proximity to its counterion, it should be possible to transfer chiral information between the ions of an ionic liquid. Indeed, the hydrogenation of a prochiral, keto-functionalized cation was found to proceed in the presence of (R)-camphorsulfonate in up to 80 % ee (see scheme).

    14. Cyclopentadienyl Zincates: Synthesis and X-ray Studies of Sodium and Potassium Salts of the [Zn(C5H5)3] and [Zn2(C5H5)5] Ions (pages 1296–1299)

      Eleuterio Alvarez, Abdessamad Grirrane, Irene Resa, Diego del Río, Amor Rodríguez and Ernesto Carmona

      Version of Record online: 5 JAN 2007 | DOI: 10.1002/anie.200603875

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      Zigzag zinc: The Na+ and K+ salts of the [Zn(C5H5)3] ion exhibit polymeric 1D and 2D structures, respectively. In contrast, the dizincate [Na(thf)6][Zn2(C5H5)5] contains discrete [Zn2(C5H5)5] ions that consist of two {Zn(C5H5)2} groups with η1(π)/η1(π) binding, bridged by a C5H5 ring η1(π)-coordinated to each zinc atom (see structure).

    15. Onionlike Hybrid Assemblies Based on Surfactant-Encapsulated Polyoxometalates (pages 1300–1303)

      Haolong Li, Hang Sun, Wei Qi, Miao Xu and Lixin Wu

      Version of Record online: 27 DEC 2006 | DOI: 10.1002/anie.200603934

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      Know your onions: Layered onionlike assemblies of surfactant-encapsulated polyoxometalates have been constructed in organic solution (see TEM image of (DODA)4SiW12O40; DODA=dimethyldioctadecylammonium). The hybrid structure arises from the rearrangement of surfactants on the polyoxometalate, which is driven by hydrophobic forces.

    16. Highly Controlled Living Radical Polymerization through Dual Activation of Organobismuthines (pages 1304–1306)

      Shigeru Yamago, Eiichi Kayahara, Masashi Kotani, Biswajit Ray, Yungwan Kwak, Atsushi Goto and Takeshi Fukuda

      Version of Record online: 5 JAN 2007 | DOI: 10.1002/anie.200604473

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      The living end: Organobismuthines promote highly controlled living radical polymerization through two activation mechanisms, namely, thermal generation and degenerative transfer (see scheme). Both conjugated and nonconjugated vinyl monomers are polymerized to give well-defined polymers with predetermined molecular weight (Mn) and low polydispersity index (PDI).

    17. Enantioselective Intramolecular Aldol Addition/Dehydration Reaction of a Macrocyclic Diketone: Synthesis of the Musk Odorants (R)-Muscone and (R,Z)-5-Muscenone (pages 1307–1310)

      Oliver Knopff, Jérôme Kuhne and Charles Fehr

      Version of Record online: 9 JAN 2007 | DOI: 10.1002/anie.200604518

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      One hundred years after the first isolation of natural (R)-muscone [(R)-1], a short and efficient access to the outstanding odorants (R)-1 and (R,Z)-5-muscenone [(R)-2] has become possible thanks to an unprecedented, reversible intramolecular aldol addition/enantioselective dehydration (up to 76 % ee; see scheme).

    18. Zeolite Shape-Selectivity in the gem-Methylation of Aromatic Hydrocarbons (pages 1311–1314)

      David Lesthaeghe, Bart De Sterck, Veronique Van Speybroeck, Guy B. Marin and Michel Waroquier

      Version of Record online: 4 JAN 2007 | DOI: 10.1002/anie.200604309

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      A glove for the purpose: The kind of olefins obtained from methanol in zeolites is strongly dependent on specific combinations of the intermediate organic hydrocarbon-pool species and zeolite topology (see picture). If the cage is too large, neutral species are favored over reactive cations. If the cage is too small, transition-state-shape selectivity poses severe limitations on the reactivity of bulkier species.

    19. Indium-Mediated Asymmetric Allylation of Acylhydrazones Using a Chiral Urea Catalyst (pages 1315–1317)

      Kian L. Tan and Eric N. Jacobsen

      Version of Record online: 9 JAN 2007 | DOI: 10.1002/anie.200603354

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      Urea-ka! A new role for urea-based chiral catalysts has been uncovered in the asymmetric allylation of acylhydrazones with allylindium reagents (see scheme; Bz: benzoyl). The best results were obtained using the bifunctional catalyst 1, which bears a Lewis basic sulfinamide. This example represents the first highly enantioselective addition of an organometallic reagent catalyzed by a chiral urea catalyst.

    20. Patterned Paper as a Platform for Inexpensive, Low-Volume, Portable Bioassays (pages 1318–1320)

      Andres W. Martinez, Scott T. Phillips, Manish J. Butte and George M. Whitesides

      Version of Record online: 9 JAN 2007 | DOI: 10.1002/anie.200603817

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      By the book: A method for patterning paper with photoresist to create well-defined, millimeter-sized channels comprising hydrophilic paper bounded by hydrophobic polymer is described. This type of patterned paper is a prototype of a class of low-cost, portable, and technically simple platforms for running multiplexed bioassays with microliter volumes of a single biological sample.

    21. Evidence for a π Dimer in the Electrochemical Reduction of 1,3,5-Trinitrobenzene: A Reversible N2-Fixation System (pages 1321–1325)

      Iluminada Gallardo, Gonzalo Guirado, Jordi Marquet and Neus Vilà

      Version of Record online: 29 DEC 2006 | DOI: 10.1002/anie.200602690

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      Electrochemical reduction of 1,3,5-trinitrobenzene (1) forms π dimer 2, which evolves to a more stable σ complex. The crystal structure of the NEt4+ salt of 2 shows π-stacked chains of radical anions. Solid 2 or dimeric 2 in solution reacts with N2 to give a dianion in which an azo group links two 1,3,5-trinitrobenzene units (see picture). The azo derivative is reversibly electrochemically oxidized to 1.

    22. Dynamic Modulation of Chemical Concentration in an Aqueous Droplet (pages 1326–1328)

      Gavin D. M. Jeffries, Jason S. Kuo and Daniel T. Chiu

      Version of Record online: 4 JAN 2007 | DOI: 10.1002/anie.200603072

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      The shrinkage factor: Chemical and biological processes are governed by the frequency of molecular collisions, which are dictated by the concentration of the dissolved species. Dynamic control over the concentrations of dissolved species in a nanoscale reaction vessel (droplet; colored pink in the picture) provides a new degree of control that will aid in the study of fundamental chemical processes.

    23. Water Gas Shift Reaction on Cu and Au Nanoparticles Supported on CeO2(111) and ZnO(000equation image): Intrinsic Activity and Importance of Support Interactions (pages 1329–1332)

      José A. Rodriguez, Ping Liu, Jan Hrbek, Jaime Evans and Manuel Pérez

      Version of Record online: 5 JAN 2007 | DOI: 10.1002/anie.200603931

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      A cerious contender: The catalytic activity in the water gas shift reaction of Au and Cu nanoparticles supported on CeO2(111) is superior to that of these nanoparticles on a ZnO(000equation image) support or of the bulk metals (the diagram shows the results depending on the Au nanoparticle coverage). These results illustrate the essential role that an oxide can have in the activity of supported Au nanocatalysts.

    24. Aggregation Behavior of Tetraenoic Fatty Acids in Aqueous Solution (pages 1333–1336)

      Yonghui Wang, Jianguo Ma, Hwan-Sung Cheon and Yoshito Kishi

      Version of Record online: 9 JAN 2007 | DOI: 10.1002/anie.200603979

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      Why so blue? Unique blue-shifted UV absorptions were used to follow the aggregation of C24 tetraene fatty acids in aqueous solution. Aggregation takes place through three distinct states (i.e. K[RIGHTWARDS ARROW]T1[RIGHTWARDS ARROW]T2; see picture). It is suggested that all of these aggregates are lamellar-type in a local sense but differ in the packing mode of the fatty acid backbone.

    25. Efficient Trapping of Oxonium Ylides with Imines: A Highly Diastereoselective Three-Component Reaction for the Synthesis of β-Amino-α-hydroxyesters with Quaternary Stereocenters (pages 1337–1339)

      Haoxi Huang, Xin Guo and Wenhao Hu

      Version of Record online: 4 JAN 2007 | DOI: 10.1002/anie.200604389

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      In one huge stride: The single-step construction of polyfunctionalized compounds with a quaternary stereocenter is possible through a highly diastereoselective multicomponent reaction of phenyldiazoacetates, alcohols, and imines (see scheme). The use of N-(tert-butylsulfinyl)imines as the imine component provides ready access to β-amino-α-hydroxyesters of high optical purity.

    26. Structural and Compositional Control in {M12} Cobalt and Nickel Coordination Clusters Detected Magnetochemically and with Cryospray Mass Spectrometry (pages 1340–1344)

      Geoffrey J. T. Cooper, Graham N. Newton, Paul Kögerler, De-Liang Long, Larry Engelhardt, Marshall Luban and Leroy Cronin

      Version of Record online: 29 JAN 2007 | DOI: 10.1002/anie.200603870

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      Control, but not a freak: A series of dodecanuclear coordination clusters of NiII and CoII with isostructural frameworks is prepared with unparalleled structural and compositional control. At different pH values, the respective clusters can be detected in solution by cryospray mass spectrometry. The positions of the metal centers in the mixed-metal clusters are determined from the magnetic properties.

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