Angewandte Chemie International Edition

Cover image for Vol. 47 Issue 20

May 5, 2008

Volume 47, Issue 20

Pages 3651–3841

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Book Review
    8. Highlights
    9. Correspondence
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Cover Picture: Zipper Assembly of Vectorial Rigid-Rod π-Stack Architectures with Red and Blue Naphthalenediimides: Toward Supramolecular Cascade n/p-Heterojunctions (Angew. Chem. Int. Ed. 20/2008) (page 3651)

      Adam L. Sisson, Naomi Sakai, Natalie Banerji, Alexandre Fürstenberg, Eric Vauthey and Stefan Matile

      Article first published online: 28 APR 2008 | DOI: 10.1002/anie.200890089

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      Artifical Leaves …are an example of functional multicomponent architectures requiring three-dimensional organization for their creation. In their Communication on page 3727 ff., S. Matile et al. work toward this demanding objective, presenting interdigitating naphthalenediimide acceptors of different color and redox potential designed to zip up along interdigitating rigid-rod donors to produce supramolecular cascade n/p-heterojunctions on solid substrates.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Book Review
    8. Highlights
    9. Correspondence
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Inside Cover: Large-Scale Synthesis of Ultrathin Bi2S3 Necklace Nanowires (Angew. Chem. Int. Ed. 20/2008) (page 3652)

      Ludovico Cademartiri, Reihaneh Malakooti, Paul G. O'Brien, Andrea Migliori, Srebri Petrov, Nazir P. Kherani and Geoffrey A. Ozin

      Article first published online: 28 APR 2008 | DOI: 10.1002/anie.200890090

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      Ultrathin necklaces of Bi2S3 nanowires can be synthesized in solution on a gram scale and using cheap and non-air-sensitive reagents, as described by G. A. Ozin and co-workers in their Communication on page 3814 ff. Despite their small size, these nanostructures show quantum confinement effects never before observed in Bi2S3 at room temperature, and a semiconductivity which bodes well for their use in flexible electronics devices.

  3. Graphical Abstract

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

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

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Book Review
    8. Highlights
    9. Correspondence
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Copper-Catalyzed C[BOND]C Coupling of Thiol Esters and Boronic Acids under Aerobic Conditions (pages 3674–3676)

      Hana Prokopcová and C. Oliver Kappe

      Article first published online: 1 APR 2008 | DOI: 10.1002/anie.200800449

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      Getting rid of palladium: Thiol esters can be cross-coupled with boronic acids to generate ketones at neutral pH by using a CuI-oxygenate catalyst under aerobic and Pd-free conditions (see scheme; S-pendant=NHtBu thiosalicyclamide). The mechanistically unique coupling is likely to proceed by a preorganized, higher oxidation state Cu species that relies on appropriately positioned ligating S-pendant groups on the thiol ester and on an additional equivalent of the boronic acid.

    2. Asymmetric Epoxidation of Olefins with Hydrogen Peroxide—Catalysis by an Aspartate-Containing Tripeptide (pages 3677–3679)

      Albrecht Berkessel

      Article first published online: 2 APR 2008 | DOI: 10.1002/anie.200705326

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      Oxidation per carboxylic acid: Upon incorporation into a suitable tripeptide, per-aspartate can epoxidize olefins that contain hydrogen-bonding groups with high enantioselectivity (up to 92 % ee). Catalytic asymmetric epoxidation can be effected with hydrogen peroxide as the terminal oxidant and carbodiimide as the stoichiometric activator for multiple acid/peracid turnovers.

  8. Correspondence

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Book Review
    8. Highlights
    9. Correspondence
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Comments on “Mirror Symmetry Breaking” of the Centrosymmetric CaCO3 Crystals with Amino Acids (pages 3680–3682)

      Meir Lahav and Leslie Leiserowitz

      Article first published online: 26 MAR 2008 | DOI: 10.1002/anie.200703491

      Symmetry violation: Recent results by Tremel and co-workers on the phase selection of calcium carbonate through the chirality of adsorbed amino acids appear to provide a deterministic route to “mirror-symmetry breaking”, which may have ramifications for the emergence of homochirality on Earth. In our view, however, the crystallization experiments violate basic rules of symmetry and we suspect the presence of chemical, biological, or other homochiral or achiral contaminants in the system.

    2. Reply to “Mirror Symmetry Breaking” of the Centrosymmetric CaCO3 Crystals with Amino Acids (pages 3683–3686)

      Niklas Loges, Stephan E. Wolf, Martin Panthöfer, Lars Müller, Marc-Christopher Reinnig, Thorsten Hoffmann and Wolfgang Tremel

      Article first published online: 10 APR 2008 | DOI: 10.1002/anie.200800120

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      Like chalk and cheese: Although the model put forward by Lahav and Leiserowitz may be quite reasonable for the crystallization of glycine in the presence of amino acids, it is not the case for the crystallization of CaCO3 (see picture). In the latter case, the amino acids present cannot be considered to be innocent molecules as they are involved as ligands in the coordination chemistry of Ca2+. New results indicate that homochiral impurities are not the driving force for the phase selection: When added intentionally, they annihilate the observed phase selectivity rather than promote it.

  9. Minireview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Book Review
    8. Highlights
    9. Correspondence
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Bacterial Acyltransferases as an Alternative for Lipase-Catalyzed Acylation for the Production of Oleochemicals and Fuels (pages 3688–3694)

      Tim Stöveken and Alexander Steinbüchel

      Article first published online: 9 APR 2008 | DOI: 10.1002/anie.200705265

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      The low specificity of bacterial acyltransferases is utilized in the development of numerous biotechnology processes for lipid modification, a field that is dominated by the use of lipases. In contrast to lipases, these reactions are catalyzed in vivo in whole-cell fermentations. Thus wax esters, thio wax esters, or fatty-acid ethyl esters, a possible substitute for biodiesel, can be derived directly from renewable resources.

  10. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Book Review
    8. Highlights
    9. Correspondence
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Mesoporous Carbon Materials: Synthesis and Modification (pages 3696–3717)

      Chengdu Liang, Zuojiang Li and Sheng Dai

      Article first published online: 18 MAR 2008 | DOI: 10.1002/anie.200702046

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      The right combination of new techniques, which use a large variety of hard and soft templates in the controlled synthesis of mesoporous carbon materials with well-defined nanostructures, and surface modification of these materials offers new perspectives for carbon material applications. The picture shows a high-resolution view of the surface structure of a fibrous material formed from phloroglucinol.

  11. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Book Review
    8. Highlights
    9. Correspondence
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. A Bioluminescent Molecular Switch For Glucose (pages 3718–3721)

      Krystal Teasley Hamorsky, C. Mark Ensor, Yinan Wei and Sylvia Daunert

      Article first published online: 27 MAR 2008 | DOI: 10.1002/anie.200704440

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      Glowing after a sugar rush: A molecular switch is formed by inserting glucose-binding protein (GBP) into aequorin (AEQ; see picture). This switch is triggered by recognition of glucose by the GBP. For the first time, AEQ is rationally split into two fragments that, upon a molecular recognition event, come together and emit bioluminescence.

    2. Simultaneous Determination of the Conformation and Relative Configuration of Archazolide A by Using Nuclear Overhauser Effects, J Couplings, and Residual Dipolar Couplings (pages 3722–3726)

      Christophe Farès, Jorma Hassfeld, Dirk Menche and Teresa Carlomagno

      Article first published online: 10 APR 2008 | DOI: 10.1002/anie.200800225

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      Combine and conquer: Configurational assignment of remote stereogenic centers in the complex polyketide macrolide archazolide A (see structure; red O, blue N, yellow S) was accomplished by a purely NMR-based approach relying on a combination of nuclear Overhauser effects, J couplings, and residual dipolar couplings (RDCs).

    3. Zipper Assembly of Vectorial Rigid-Rod π-Stack Architectures with Red and Blue Naphthalenediimides: Toward Supramolecular Cascade n/p-Heterojunctions (pages 3727–3729)

      Adam L. Sisson, Naomi Sakai, Natalie Banerji, Alexandre Fürstenberg, Eric Vauthey and Stefan Matile

      Article first published online: 25 MAR 2008 | DOI: 10.1002/anie.200800203

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      Zipped up: Supramolecular 3D organization on gold with interdigitating intra- and interlayer recognition motifs (see picure, black p-oligophenyl rods; red, blue naphthalenediimide (NDI) stacks) is designed to access supramolecular cascade n/p-heterojunctions or the adaptable directionality needed to control fill factors in current–voltage curves.

    4. Water-Soluble Nanocrystals Through Dual-Interaction Ligands (pages 3730–3734)

      Huimeng Wu, Haizhen Zhu, Jiaqi Zhuang, Shuo Yang, Chen Liu and Y. Charles Cao

      Article first published online: 9 APR 2008 | DOI: 10.1002/anie.200800434

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      No fear of water: Hydrophobic nanocrystals (NCs) are converted into hydrophilic ones by dual-interaction ligands, which bind onto the surface of NCs by coordinate bonding and hydrophobic van der Waals interactions. The resulting NCs have high stability in aqueous solutions over a wide pH range (1–14), salt concentrations, and thermal treatments. Quantum dots coated with these ligands are excellent fluorescence labels for immunostaining tests.

    5. A Highly Selective Luminescent Switch-On Probe for Histidine/Histidine-Rich Proteins and Its Application in Protein Staining (pages 3735–3739)

      Dik-Lung Ma, Wing-Leung Wong, Wai-Hong Chung, Fung-Yi Chan, Pui-Kin So, Tat-Shing Lai, Zhong-Yuan Zhou, Yun-Chung Leung and Kwok-Yin Wong

      Article first published online: 15 APR 2008 | DOI: 10.1002/anie.200705319

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      No destaining required: The luminescence properties of an iridium(III)–2-phenylpyridine complex can be utilized for the detection of proteins in sodium dodecyl sulfate–polyacrylamide gels. Emissive gel images obtained upon staining with the complex are visible under UV light. The high detection sensitivity for histidine-rich proteins (right vial, compared to a non-histidine-tagged protein) suggests potential applications in the signaling of biomolecules.

    6. 1,2,3-Triazole CH⋅⋅⋅Cl Contacts Guide Anion Binding and Concomitant Folding in 1,4-Diaryl Triazole Oligomers (pages 3740–3743)

      Hemraj Juwarker, Jeremy M. Lenhardt, David M. Pham and Stephen L. Craig

      Article first published online: 8 APR 2008 | DOI: 10.1002/anie.200800548

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      A new folder: The electropositive CH groups of diaryl triazoles interact favourably with chloride, leading to anion-induced helical folding in aryl triazole oligomers. Triazoles thus provide an alternative to conventional protic hydrogen bonds and coordination complexes as functional components in anion receptors.

    7. A Caged Retinoic Acid for One- and Two-Photon Excitation in Zebrafish Embryos (pages 3744–3746)

      Pierre Neveu, Isabelle Aujard, Chouaha Benbrahim, Thomas Le Saux, Jean-François Allemand, Sophie Vriz, David Bensimon and Ludovic Jullien

      Article first published online: 10 APR 2008 | DOI: 10.1002/anie.200800037

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      Escaping the cage: Retinoic acid (RA), a crucial signaling molecule for the embryogenesis of vertebrates, can be photoreleased from a simple caged derivative (cRA) upon illumination. In zebrafish embryos, cRA causes RA-induced phenotypes with one- and two-photon excitation (see picture), which opens a route to the noninvasive generation of controlled RA concentration patterns in vivo.

    8. Development of Selective RabGGTase Inhibitors and Crystal Structure of a RabGGTase–Inhibitor Complex (pages 3747–3750)

      Zhong Guo, Yao-Wen Wu, Kui-Thong Tan, Robin S. Bon, Ester Guiu-Rozas, Christine Delon, Uyen T. Nguyen, Stefan Wetzel, Sabine Arndt, Roger S. Goody, Wulf Blankenfeldt, Kirill Alexandrov and Herbert Waldmann

      Article first published online: 10 APR 2008 | DOI: 10.1002/anie.200705795

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      Stopping the transfer: Based on the structure of pepticinnamin E, specific inhibitors of Rab geranylgeranyl transferase (RabGGTase) with activity in cells were developed, and the first crystal structure of the enzyme in complex with an inhibitor is reported (see inhibitor structure and positioning in the active site of the enzyme). The findings may have implications for the chemical-biological study of Rab prenylation and vesicular transport and the involvement of RabGGTase in the establishment of disease.

    9. Protein-Cross-Linked Polymeric Materials through Site-Selective Bioconjugation (pages 3751–3754)

      Aaron P. Esser-Kahn and Matthew B. Francis

      Article first published online: 10 APR 2008 | DOI: 10.1002/anie.200705564

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      Creating a greener future: A strategy for creating hybrid materials of polymers and proteins relies on orthogonal reactions to activate the N and C termini of a protein concurrently. The protein is then used to cross-link polymer chains and create a hydrogel (see picture). A model hybrid hydrogel containing enhanced green fluorescent protein is both biodegradable and responsive to changes in pH and temperature.

    10. Synthesis of (−)-Octalactin A by a Strategic Vanadium-Catalyzed Oxidative Kinetic Resolution (pages 3755–3758)

      Alexander T. Radosevich, Vincent S. Chan, Hui-Wen Shih and F. Dean Toste

      Article first published online: 10 APR 2008 | DOI: 10.1002/anie.200800554

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      Both products of the kinetic resolution were used in the resolution/recombination approach shown in the scheme for the enantioselective total synthesis of (−)-octalactin A. Bn=benzyl, TBS=tert-butyldimethylsilyl.

    11. A Concise Synthesis of (−)-Oseltamivir (pages 3759–3761)

      Barry M. Trost and Ting Zhang

      Article first published online: 10 APR 2008 | DOI: 10.1002/anie.200800282

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      Tackling the supply problem: A short and efficient synthesis of (−)-oseltamivir has been developed which requires eight steps from commercially available starting material and proceeds with an overall yield of 30 %. Key transformations include a novel palladium-catalyzed asymmetric allylic alkylation reaction (Pd-AAA, see scheme) as well as a chemo-, regio-, and stereoselective aziridination reaction. Phth=phthaloyl.

    12. Total Synthesis of (+)-Oocydin A: Application of the Suzuki–Miyaura Cross-Coupling of 1,1-Dichloro-1-alkenes with 9-Alkyl 9-BBN (pages 3762–3765)

      Emmanuel Roulland

      Article first published online: 10 APR 2008 | DOI: 10.1002/anie.200800585

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      Two sensitive fragments were coupled in the mild title reaction to create the Z-chlorovinyl functionality of the target macrolide oocydin A (1; see scheme). Another highlight in the total synthesis of 1 was an efficient stereoselective Pd0-catalyzed cyclization to form the highly substituted tetrahydrofuran ring. Bz=benzoyl, TBS=tert-butyldimethylsilyl, MPM=4-methoxyphenylmethyl.

    13. Heterobimetallic Cooperation Mediates the Transformation of White Phosphorus into Zwitterionic catena-Phosphonium(+)diphosphenide(−) Ligands (pages 3766–3768)

      Maria Caporali, Pierluigi Barbaro, Luca Gonsalvi, Andrea Ienco, Dmitry Yakhvarov and Maurizio Peruzzini

      Article first published online: 15 APR 2008 | DOI: 10.1002/anie.200800470

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      White phosphorus is sequentially activated and functionalized by stepwise reaction with cobalt and platinum metal complexes. The two zwitterionic diphenyl(alkyl)phosphonium(+)diphosphenide(−) molecules generated act as bridging side-on/end-on ligands that tether two different metal units (see picture of the complex core: C black, Co pale green, P orange, Pt green).

    14. A Transient VIII–Alkylidene Complex: Oxidation Chemistry Including the Activation of N2 to Afford a Highly Porous Honeycomb-Like Framework (pages 3769–3772)

      Uriah J. Kilgore, Caitlin A. Sengelaub, Maren Pink, Alison R. Fout and Daniel J. Mindiola

      Article first published online: 8 APR 2008 | DOI: 10.1002/anie.200705931

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      Honeycomb architectures from N2sequestration! The VIII–bis-neopentyl complex [(PNP)V(CH2tBu)2] (PNP=N[4-Me-2-(PiPr2)C6H3]2) is a synthon to terminal VV alkylidene complexes when treated with two-electron oxidants such as N2CPh2, O2− sources such as OPPh3 and N2O, and sulfide sources like S8 and SPPh3. The likely VIII–alkylidene intermediate, [(PNP)V[DOUBLE BOND]CHtBu], can also activate N2 to form a honeycomb-like packing rearrangement along the N2 unit (see picture).

    15. The “Complex-in-a-Complex” Cations [(acac)2M⊂Ru6(p-iPrC6H4Me)6(tpt)2(dhbq)3]6+: A Trojan Horse for Cancer Cells (pages 3773–3776)

      Bruno Therrien, Georg Süss-Fink, Padavattan Govindaswamy, Anna K. Renfrew and Paul J. Dyson

      Article first published online: 15 APR 2008 | DOI: 10.1002/anie.200800186

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      The start of an odyssey? The cytotoxicities of the large cationic arene–ruthenium prismatic cage 16+, and its “complex-in-a-complex” derivatives [(acac)2M⊂1]6+ (M=Pd, Pt; acac=acetylacetonate; see picture), are evaluated in comparison with free [M(acac)2]. The differences in cytotoxicity suggest that, like a “Trojan Horse”, leaching of the guest from the cage once inside a cell accelerates and increases the cytotoxic effect.

    16. Enantioselective Copper-Catalyzed Propargylic Amination (pages 3777–3780)

      Remko J. Detz, Mariëlle M. E. Delville, Henk Hiemstra and Jan H. van Maarseveen

      Article first published online: 18 FEB 2008 | DOI: 10.1002/anie.200705264

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      A proper copper catalyst with a chiral pyridine-2,6-bisoxazoline (pybox) ligand was used to convert a variety of propargylic acetates with aromatic side chains (R=Ar) into their amine counterparts in high yield and with good selectivity (up to 88 % ee). The resulting chiral propargylic amines can be elaborated further into P,N ligands (see scheme; DIPEA=diisopropylethylamine).

    17. Copper-Catalyzed Asymmetric Propargylic Substitution Reactions of Propargylic Acetates with Amines (pages 3781–3783)

      Gaku Hattori, Hiroshi Matsuzawa, Yoshihiro Miyake and Yoshiaki Nishibayashi

      Article first published online: 11 APR 2008 | DOI: 10.1002/anie.200800276

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      Flexing your bipheps: Enantioselective propargylic substitution reactions of propargylic acetates with amines catalyzed by a copper-(R)-Cl-MeO-biphep or -binap complex give the corresponding propargylic amines in excellent yields with up to 89 % ee. The reaction described may provide a novel synthetic method for the preparation of chiral propargylic amines.

    18. An Annulation Reaction for the Synthesis of Morpholines, Thiomorpholines, and Piperazines from β-Heteroatom Amino Compounds and Vinyl Sulfonium Salts (pages 3784–3786)

      Muhammad Yar, Eoghan M. McGarrigle and Varinder K. Aggarwal

      Article first published online: 11 APR 2008 | DOI: 10.1002/anie.200800373

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      Heterocycling: Diphenyl vinyl sulfonium salt 1 acts first as an electrophile, then a base, and then again as an electrophile in this operationally simple, high yielding, one-pot synthesis of pharmacologically important morpholines, thiomorpholines, and piperazines. Compound 1 is an excellent synthon for the 1,2-ethane dication.

    19. A Chiral Hypervalent Iodine(III) Reagent for Enantioselective Dearomatization of Phenols (pages 3787–3790)

      Toshifumi Dohi, Akinobu Maruyama, Naoko Takenaga, Kento Senami, Yutaka Minamitsuji, Hiromichi Fujioka, Simon B. Caemmerer and Yasuyuki Kita

      Article first published online: 4 APR 2008 | DOI: 10.1002/anie.200800464

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      The hype about iodine(III): A chiral hypervalent iodine(III) reagent (1) is reported to enantioselectively dearomatize phenols in a highly selective manner (see scheme). This result clearly supports existence of the associative pathway in hypervalent iodine(III)-induced phenolic oxidations.

    20. The Versatile Chemistry and Noncentrosymmetric Crystal Structures of Salt-Inclusion Vanadate Hybrids (pages 3791–3794)

      Wendy L. Queen, J. Palmer West, Shiou-Jyh Hwu, Donald G. VanDerveer, Matthew C. Zarzyczny and Ryan A. Pavlick

      Article first published online: 9 APR 2008 | DOI: 10.1002/anie.200705113

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      Acentric vanadates: Three unique structure types of the vanadate-based mixed-metal oxide systems (salt)⋅MnII-VV-O and (salt)⋅CuII-VV-O are presented, with a focus on the role of the asymmetric vanadate units (yellow polyhedra). The two structure types found in the (AX)2M(VO3)2 series differ in the propagation direction of the metavanadate chains, which is thought to be due to the presence (or absence) of a Jahn–Teller distortion of the metal (d9 Cu2+ vs. d5 Mn2+) ion.

    21. Enantioselective O-Nitroso Aldol Reaction of Silyl Enol Ethers (pages 3795–3797)

      Masanori Kawasaki, Pingfan Li and Hisashi Yamamoto

      Article first published online: 26 FEB 2008 | DOI: 10.1002/anie.200705679

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      New nucleophiles for the O-nitroso aldol reaction in the form of readily prepared disilanyl enol ethers make this transformation more practical and more versatile. A silver catalyst with a chiral biaryl phosphite ligand promotes the title reaction with high enantio- and regioselectivity (see scheme). R1,R2 = H, Ar; TMS = trimethylsilyl.

    22. The Influence of Guanine on DNA Hole Transport Efficiency (pages 3798–3800)

      Frederick D. Lewis, Pierre Daublain, Boiko Cohen, Josh Vura-Weis and Michael R. Wasielewski

      Article first published online: 8 APR 2008 | DOI: 10.1002/anie.200705903

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      Stopover at G base: The efficiency of photoinduced charge separation between donor and acceptor chromophores separated by a polyadenine sequence containing a single guanine (G) is sensitive to the location of G and the total length of the polypurine sequence. Quantum yields provide support for a stepwise mechanism in which G serves as a temporary resting place in the overall process (Sa: stilbenedicarboxamide electron acceptor, Sd: stilbenediether electron donor).

    23. The Low Basicity of Phosphabenzenes: First Examples of Protonation, Alkylation, and Silylation Reactions (pages 3801–3804)

      Yun Zhang, Fook S. Tham, John F. Nixon, Charlotte Taylor, Jennifer C. Green and Christopher A. Reed

      Article first published online: 15 APR 2008 | DOI: 10.1002/anie.200800878

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      Strong yet gentle: Where triflate reagents fail, carborane-based sources of H+, CH3+, and [R3Si]+ electrophiles add to phosphabenzenes preferentially at the P atom rather than C (see picture).

    24. A Highly Efficient and Selective AuI-Catalyzed Tandem Synthesis of Diversely Substituted Pyrrolo[1,2-a]quinolines in Aqueous Media (pages 3805–3810)

      Xin-Yuan Liu and Chi-Ming Che

      Article first published online: 10 APR 2008 | DOI: 10.1002/anie.200800160

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      Bicycles built in water: The AuI-catalyzed tandem cyclization of 1-amino-4-alkynes with alkynes in water offers a simple and efficient method for the synthesis of diversely substituted pyrrolo[1,2-a]quinolines with good to excellent product yields and excellent regio- and chemoselectivities (see scheme).

    25. Fluorescence-Quenching-Based Enzyme-Activity Assay by Using Photon Upconversion (pages 3811–3813)

      Terhi Rantanen, Marja-Leena Järvenpää, Johanna Vuojola, Katri Kuningas and Tero Soukka

      Article first published online: 10 APR 2008 | DOI: 10.1002/anie.200705861

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      Switch the lights off! A novel sensitive enzyme-activity assay combines the advantageous features of upconverting phosphors (UCPs) and fluorescence quenching. The new assay principle allows the use of fluorescent particulate labels in a quenching-based assay despite the fact that it is not possible to achieve adequate quenching efficiency of particle fluorescence directly. Infrared excitation enables even the use of colorful samples.

    26. Large-Scale Synthesis of Ultrathin Bi2S3 Necklace Nanowires (pages 3814–3817)

      Ludovico Cademartiri, Reihaneh Malakooti, Paul G. O'Brien, Andrea Migliori, Srebri Petrov, Nazir P. Kherani and Geoffrey A. Ozin

      Article first published online: 9 APR 2008 | DOI: 10.1002/anie.200705034

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      Think thin! Colloidally stable ultrathin Bi2S3 nanowires (see picture), which display strong excitonic features never before seen in bismuth chalcogenides and extremely high extinction coefficients, have been synthesized on a gram-scale. Nanostructures such as this are of very high technological potential for thermoelectric applications.

    27. Catalytic Asymmetric C[BOND]Si Bond Formation to Acyclic α,β-Unsaturated Acceptors by RhI-Catalyzed Conjugate Silyl Transfer Using a Si[BOND]B Linkage (pages 3818–3820)

      Christian Walter and Martin Oestreich

      Article first published online: 3 APR 2008 | DOI: 10.1002/anie.200800361

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      A perfect match: The RhI-catalyzed conjugate silylation of acyclic Z-configured α,β-unsaturated carboxyl compounds including imides with silylboronic ester yields almost enantiopure α-chiral quaternary silanes (see scheme; R=aryl and (branched) alkyl, cod=cycloocta-1,5-diene, pin=pinacolato).

    28. Hierarchically Self-Assembled Host–Guest Network at the Solid–Liquid Interface for Single-Molecule Manipulation (pages 3821–3825)

      Christoph Meier, Katharina Landfester, Daniela Künzel, Thomas Markert, Axel Groß and Ulrich Ziener

      Article first published online: 8 APR 2008 | DOI: 10.1002/anie.200705527

      Thumbnail image of graphical abstract

      Now you see it, now you don't: A molecular monolayer polymorph of an oligopyridine forms a host–guest network with copper(II) phthalocyanine at the solid–liquid interface with controllable phthalocyanine occupation. The slow movement of the phthalocyanine guest molecules and the competition between oligopyridine and phthalocyanine guest molecules make it possible to manipulate individual guest molecules in analogy to “writing” and “erasing”.

    29. Synthesis of a Paramagnetic Polymer by Ring-Opening Polymerization of a Strained [1]Vanadoarenophane (pages 3826–3829)

      Holger Braunschweig, Christopher J. Adams, Thomas Kupfer, Ian Manners, Robert M. Richardson and George R. Whittell

      Article first published online: 7 APR 2008 | DOI: 10.1002/anie.200800081

      Thumbnail image of graphical abstract

      Salt-elimination reactions led to the formation of highly strained [1]bora- and [1]silavanadoarenophanes, which undergo different types of ring-opening reactions with low-valent platinum complexes. Whereas the boron-bridged derivative opened stoichiometrically by cleavage of the V[BOND]Carene bond, the [1]silavanadoarenophane reacted at the Si[BOND]Cipso bond to afford a polymer containing spin-active metal centers in the main chain (see scheme).

    30. The Cation–Anion Interaction in Ionic Liquids Probed by Far-Infrared Spectroscopy (pages 3830–3834)

      Koichi Fumino, Alexander Wulf and Ralf Ludwig

      Article first published online: 15 APR 2008 | DOI: 10.1002/anie.200705736

      Thumbnail image of graphical abstract

      Bending and stretching: The nature of intermolecular interactions in imidazolium-based ionic liquids has been studied by far-infrared spectroscopy. The lowest frequencies can be assigned to the bending and stretching vibrational modes of the cation–anion interaction, which describes the cohesion energy.

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      Preview: Angew. Chem. Int. Ed. 21/2008 (page 3841)

      Article first published online: 28 APR 2008 | DOI: 10.1002/anie.200890094

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