Angewandte Chemie International Edition

Cover image for Vol. 48 Issue 10

February 23, 2009

Volume 48, Issue 10

Pages 1697–1865

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Reviews
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Cover Picture: Heterogeneously Hybridized Porous Coordination Polymer Crystals: Fabrication of Heterometallic Core–Shell Single Crystals with an In-Plane Rotational Epitaxial Relationship (Angew. Chem. Int. Ed. 10/2009) (page 1697)

      Shuhei Furukawa, Kenji Hirai, Keiji Nakagawa, Yohei Takashima, Ryotaro Matsuda, Takaaki Tsuruoka, Mio Kondo, Rie Haruki, Daisuke Tanaka, Hirotoshi Sakamoto, Satoru Shimomura, Osami Sakata and Susumu Kitagawa

      Version of Record online: 17 FEB 2009 | DOI: 10.1002/anie.200990041

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      A porous copper coordination framework grew epitaxially as a single crystal on the surface of a single crystal of a porous zinc coordination framework, as described by S. Kitagawa and co-workers in their Communication on page 1766 ff. The picture shows the structural relationship between the copper and zinc frameworks, which has been unveiled by synchrotron surface X-ray diffraction measurements; in-plane rotational epitaxial growth compensates for the different lattice constants of the two crystals.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Reviews
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Inside Cover: A Synthetic Lectin for O-Linked β-N-Acetylglucosamine (Angew. Chem. Int. Ed. 10/2009) (page 1698)

      Yann Ferrand, Emmanuel Klein, Nicholas P. Barwell, Matthew P. Crump, Jesus Jiménez-Barbero, Cristina Vicent, Geert-Jan Boons, Sampat Ingale and Anthony P. Davis

      Version of Record online: 17 FEB 2009 | DOI: 10.1002/anie.200990042

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      Carbohydrates are slippery customers in water. Camouflaged by solvent-mimicking hydroxy groups, they make challenging targets, even for natural receptors. In their Communication on page 1775 ff., A. P. Davis and co-workers describe a synthetic receptor that is remarkably effective for the important β-N-acetylglucosaminyl (β-GlcNAC) unit. The affinities of the receptor are good and its selectivities are excellent, even by the standards of natural carbohydrate-binding proteins.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Reviews
    9. Highlights
    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. Author Profile
    8. Book Reviews
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. You have free access to this content
      Highly Efficient and Thermally Stable Organic Sensitizers for Solvent-Free Dye-Sensitized Solar Cells (page 1712)

      Hyunbong Choi, Chul Baik, Sang Ook Kang, Jaejung Ko, Moon-Sung Kang, Md. K. Nazeeruddin and Michael Grätzel

      Version of Record online: 17 FEB 2009 | DOI: 10.1002/anie.200990044

      This article corrects:
  5. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Reviews
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Alan E. Rowan (page 1717)

      Version of Record online: 17 FEB 2009 | DOI: 10.1002/anie.200990047

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      “I chose chemistry as a career because… I like the creative challenge. My favorite subjects at school were mathematics and music…!” These facts and more information about Alan E. Rowan can be found on page 1717

  7. Book Reviews

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

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

      Synthetic Lectins (pages 1722–1725)

      Stefan Kubik

      Version of Record online: 29 DEC 2008 | DOI: 10.1002/anie.200805497

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      Improving on Mother Nature? The carbohydrate recognition demonstrated by supramolecular systems in water can now compete with that of natural systems, both in terms of affinity and selectivity. A synthetic carbohydrate receptor displays similar affinity for N-acetyl-D-glucosamine derivatives as the lectin wheat germ agglutinin and even greater selectivity (see picture: gray C, white H, blue N, red O).

    2. Radical Reduction

      Linking Borane with N-Heterocyclic Carbenes: Effective Hydrogen-Atom Donors for Radical Reactions (pages 1726–1728)

      John C. Walton

      Version of Record online: 27 JAN 2009 | DOI: 10.1002/anie.200805362

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      Undue influence: N-heterocyclic carbenes (NHCs) were found to reduce the strength of the B[BOND]H bonds of borane by a surprisingly large amount upon the formation of NHC–BH3 complexes. This property was exploited in the development of a suite of NHC–borane complexes for the reduction of xanthates in radical-mediated Barton–McCombie-type deoxygenation reactions (see scheme). AIBN=azobisisobutyronitrile, Bn=benzyl.

    3. Protein Modification

      Bioorthogonal Ligation in the Spotlight (pages 1729–1731)

      Thomas Kurpiers and Henning D. Mootz

      Version of Record online: 15 JAN 2009 | DOI: 10.1002/anie.200805454

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      The light-induced formation of a covalent bond between an alkene group and a tetrazole moiety has been used for the selective labeling of proteins in vitro and in live cells. This bioorthogonal ligation initiated by brief irradiation with UV light leads to a fluorescent pyrazoline adduct (see scheme).

  9. Minireview

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

      Local Probe Oxidation of Self-Assembled Monolayers: Templates for the Assembly of Functional Nanostructures (pages 1732–1739)

      Daan Wouters, Stephanie Hoeppener and Ulrich S. Schubert

      Version of Record online: 22 JAN 2009 | DOI: 10.1002/anie.200801013

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      Surfaces with purposes: The electroinitiated patterning of self-assembled monolayers enables the fabrication of a variety of complex nanostructures (see picture). The possibilities offered by the introduction of chemical selectivity through the local generation of chemically active groups and subsequent derivatization are reviewed, with a focus on progress in this area of research over the last four years.

  10. Review

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

      Development of Tau Aggregation Inhibitors for Alzheimer's Disease (pages 1740–1752)

      Bruno Bulic, Marcus Pickhardt, Boris Schmidt, Eva-Maria Mandelkow, Herbert Waldmann and Eckhard Mandelkow

      Version of Record online: 2 FEB 2009 | DOI: 10.1002/anie.200802621

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      Small molecules against Alzheimer's: The pathological aggregation of the tau protein is a major hallmark of neurodegenerative diseases such as Alzheimer's disease. The inhibition or reversal of tau aggregation is a potential therapeutic strategy that is currently undergoing clinical trials. The image shows pathological fibers assembled from tau protein, which are the main components of the neurofibrillary tangles of Alzheimer's disease.

  11. Communications

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

      Sequential Assembly of Phototunable Ferromagnetic Ultrathin Films with Perpendicular Magnetic Anisotropy (pages 1754–1757)

      Masayuki Suda and Yasuaki Einaga

      Version of Record online: 9 JAN 2009 | DOI: 10.1002/anie.200804894

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      Getting organized: Assemblies of ferromagnetic FePt nanoparticles were generated with large perpendicular magnetic anisotropy by a magnetic-field-assisted layer-by-layer method, and subsequently layer-by-layer films consisting of L10-FePt nanoparticles and organic polymers were prepared. These films are phototunable when photochromic molecules are used as polymer layers.

    2. Protein Folding

      Fast Biosynthesis of GFP Molecules: A Single-Molecule Fluorescence Study (pages 1758–1761)

      Alexandros Katranidis, Diaa Atta, Ramona Schlesinger, Knud H. Nierhaus, Theodora Choli-Papadopoulou, Ingo Gregor, Michael Gerrits, Georg Büldt and Jörg Fitter

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/anie.200806070

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      It's not easy being green: Real-time visualization of labeled ribosomes and de novo synthesized green fluorescent protein molecules using single-molecule-sensitive fluorescence microscopy demonstrates that the mutant GFPem is produced with a characteristic time of five minutes. Fluorescence of the fastest GFP molecules appears within one minute (see picture).

    3. Surface Structures

      Patterned Monolayers of Neutral and Charged Functionalized Manganese Arene Complexes on a Highly Ordered Pyrolytic Graphite Surface (pages 1762–1765)

      Sang Bok Kim, Robert D. Pike, Jason S. D'Acchioli, Brennan J. Walder, Gene B. Carpenter and Dwight A. Sweigart

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/anie.200805760

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      Complex patterns: The arene manganese tricarbonyl complexes [Mn(η5-2,5-didodecoxy-1,4-semiquinone)(CO)3] and [Mn(η6-1,4-dioctyloxybenzene)(CO)3] BF4 form patterned monolayers on the surface of highly ordered pyrolytic graphite (HOPG), as a result of hydrogen-bonding, hydrophobic, and electrostatic interactions, leading to an ordered 2D array of manganese atoms or ions.

    4. Metal–Organic Frameworks

      Heterogeneously Hybridized Porous Coordination Polymer Crystals: Fabrication of Heterometallic Core–Shell Single Crystals with an In-Plane Rotational Epitaxial Relationship (pages 1766–1770)

      Shuhei Furukawa, Kenji Hirai, Keiji Nakagawa, Yohei Takashima, Ryotaro Matsuda, Takaaki Tsuruoka, Mio Kondo, Rie Haruki, Daisuke Tanaka, Hirotoshi Sakamoto, Satoru Shimomura, Osami Sakata and Susumu Kitagawa

      Version of Record online: 12 DEC 2008 | DOI: 10.1002/anie.200804836

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      MOF on MOF: Core–shell porous coordination polymer (PCP) crystals are fabricated at the single-crystal level by epitaxial growth in solution. Synchrotron X-ray diffraction measurements unveiled the structural relationship between the shell crystal and the core crystal, where in-plane rotational epitaxial growth compensates the difference in lattice constant.

    5. Sensors

      Protein Recognition by an Ensemble of Fluorescent DNA G-Quadruplexes (pages 1771–1774)

      David Margulies and Andrew D. Hamilton

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/anie.200804887

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      Sniffing out proteins: Fluorescent DNA G-quadruplexes have been used for building versatile signaling receptors for proteins in a single solution. Introducing a protein sample to the ensemble results in a unique emission signature for unambiguous identification (see scheme, R=fluorophore). The self-assembled, pattern-based protein detection systems are easily fabricated, have the potential for high-throughput operations, and have the ability to handle small protein samples.

    6. Carbohydrate Recognition

      A Synthetic Lectin for O-Linked β-N-Acetylglucosamine (pages 1775–1779)

      Yann Ferrand, Emmanuel Klein, Nicholas P. Barwell, Matthew P. Crump, Jesus Jiménez-Barbero, Cristina Vicent, Geert-Jan Boons, Sampat Ingale and Anthony P. Davis

      Version of Record online: 15 DEC 2008 | DOI: 10.1002/anie.200804905

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      Changing employment: Receptor 1 binds β-N-acetylglucosaminyl (β-GlcNAc) up to 100 times more strongly than it does glucose. This synthetic lectin shows affinities similar to wheat germ agglutinin (WGA), a natural lectin used to bind GlcNAc. Remarkably, 1 is more selective than WGA. It favors especially the glycoside unit in glycopeptide 2, a model of the serine-O-GlcNAc posttranslational protein modification.

    7. Shape-Selective Oxidation

      Shape-Selective Interception by Hydrocarbons of the O2-Derived Oxidant of a Biomimetic Nonheme Iron Complex (pages 1780–1783)

      Anusree Mukherjee, Marlène Martinho, Emile L. Bominaar, Eckard Münck and Lawrence Que Jr.

      Version of Record online: 29 JAN 2009 | DOI: 10.1002/anie.200805342

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      Picky ferryl: The complex [Fe(Tpmath image)(BF)] (Tpmath image=hydrotris(3,5-diphenylpyrazolyl)borate; BF=benzoylformate) reacts with O2 to generate an oxidant (see picture; O red, pink; Fe yellow; N blue; C gray; H white) that oxidizes added hydrocarbons shape-selectively. Discrimination derives from a cleft formed by two phenyl groups of the Tpmath image ligand, favoring oblate spheroidal substrates.

    8. Conformational Analysis

      Evidence for a Stereoelectronic Effect in Human Oxygen Sensing (pages 1784–1787)

      Christoph Loenarz, Jasmin Mecinović, Rasheduzzaman Chowdhury, Luke A. McNeill, Emily Flashman and Christopher J. Schofield

      Version of Record online: 29 JAN 2009 | DOI: 10.1002/anie.200805427

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      How PHDs achieve specificity: trans-4-prolyl hydroxylation of the transcription factor HIF occurs with stereochemical retention. Substrate-analogue studies show how the von Hippel Lindau tumor suppressor protein (pVHL) and the oxygen-sensing hydroxylases (PHDs) achieve specificity for hydroxyprolyl/prolyl residues for the C4-exo/endo prolyl conformations, respectively.

    9. Crude Oil Analysis

      Characterization of Supercomplex Crude Oil Mixtures: What Is Really in There? (pages 1788–1791)

      Saroj K. Panda, Jan T. Andersson and Wolfgang Schrader

      Version of Record online: 27 JAN 2009 | DOI: 10.1002/anie.200803403

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      Through different windows: One major obstacle in energy research is the complexity and variety of compounds present in crude oil. A study of different ionization methods for mass spectrometry shows that the mass spectrum very strongly depends on which method is used.

    10. Molecular Electronics

      A Bistable Poly[2]catenane Forms Nanosuperstructures (pages 1792–1797)

      Mark A. Olson, Adam B. Braunschweig, Lei Fang, Taichi Ikeda, Rafal Klajn, Ali Trabolsi, Paul J. Wesson, Diego Benítez, Chad A. Mirkin, Bartosz A. Grzybowski and J. Fraser Stoddart

      Version of Record online: 29 JAN 2009 | DOI: 10.1002/anie.200804558

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      Side-chain poly[2]catenanes at the click of a switch! A bistable side-chain poly[2]catenane has been synthesized and found to form hierarchical self-assembled hollow superstructures of nanoscale dimensions in solution. Molecular electromechanical switching (see picture) of the material is demonstrated, and the ground-state equilibrium thermodynamics and switching kinetics are examined as the initial steps towards processible molecular-based electronic devices and nanoelectromechanical systems.

    11. Supramolecular Gels

      Responsive Supramolecular Gels Constructed by Crown Ether Based Molecular Recognition (pages 1798–1802)

      Zhishen Ge, Jinming Hu, Feihe Huang and Shiyong Liu

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/anie.200805712

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      Responsive supramolecular gels were constructed from crown ether terminated four-arm star poly(ε-caprolactone) (PCL–DB24C8) and dibenzylammonium-terminated two-arm PCL–DBAS (see scheme), exploiting the formation of pseudorotaxane linkages between crown ether and ammonium moieties. The resultant supramolecular gels exhibit thermo- and pH-induced reversible gel–sol transition.

    12. Enzyme Models

      Water as an Oxygen Source in the Generation of Mononuclear Nonheme Iron(IV) Oxo Complexes (pages 1803–1806)

      Yong-Min Lee, Sunder N. Dhuri, Sarvesh C. Sawant, Jaeheung Cho, Minoru Kubo, Takashi Ogura, Shunichi Fukuzumi and Wonwoo Nam

      Version of Record online: 13 JAN 2009 | DOI: 10.1002/anie.200805670

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      Give me an “O”! Mononuclear nonheme iron(IV) oxo complexes have been generated using water as an oxygen source and cerium(IV) as an oxidant. The high-yield oxygenation of organic substrates in this system (see picture, Fe green, O red, N blue, C gray) is catalyzed by iron(II) complexes. The source of oxygen in the iron(IV) oxo complexes and the oxygenated products has been assigned unambiguously by isotopic labeling experiments.

    13. Vesicle-Based Drug Delivery

      Near-IR Remote Release from Assemblies of Liposomes and Nanoparticles (pages 1807–1809)

      Dmitry V. Volodkin, Andre G. Skirtach and Helmuth Möhwald

      Version of Record online: 27 JAN 2009 | DOI: 10.1002/anie.200805572

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      Set free by light: Near-IR (NIR) laser-initiated remote release of fluorescent dye from complexes of liposome–gold-nanoparticle aggregates is demonstrated (see fluorescence images). Complexes of the desired size are shown to be a viable approach to the construction of vesicle-based drug-delivery systems with light-triggered remote release characteristics. This opens up a new method to manipulate liposome-based drug-delivery systems in a biocompatible way by using the near-IR spectral range.

    14. Cycloaddition Catalysts

      Air-Stable {(C5H5)Co} Catalysts for [2+2+2] Cycloadditions (pages 1810–1813)

      Anaïs Geny, Nicolas Agenet, Laura Iannazzo, Max Malacria, Corinne Aubert and Vincent Gandon

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/anie.200806001

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      Cobalt cyclopentadienyl complexes incorporating a fumarate and a CO ligand (see picture) efficiently catalyze inter- and intramolecular [2+2+2] cycloadditions of alkynes, nitriles, and/or alkenes to give benzenes, pyridines, or 1,3-cyclohexadienes. Unlike catalysts such as [CpCo(CO)2] or [CpCo(C2H4)2] (Cp=C5H5), they are air-stable, easy to handle, compatible with microwave conditions, and do not necessarily require irradiation to be active.

    15. Nanostructures

      Cobalt Growth on the Tips of CdSe Nanorods (pages 1814–1817)

      Jérôme Maynadié, Asaf Salant, Andrea Falqui, Marc Respaud, Ehud Shaviv, Uri Banin, Katerina Soulantica and Bruno Chaudret

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/anie.200804798

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      Best of both worlds: Reduction of an organometallic Co precursor on preformed CdSe nanorods yields two distinct semiconducting–magnetic heterostructures (see picture). The selective growth of Co on the tips of CdSe first gives nanosphere–nanorod dimers, which evolve into nanorod–nanorod structures. In the hybrid objects the magnetic properties of Co remain intact, while the luminescence properties of CdSe are affected but not completely quenched.

    16. Catalytic C[BOND]F Activation

      C[BOND]F Activation at Rhodium Boryl Complexes: Formation of 2-Fluoroalkyl-1,3,2-Dioxaborolanes by Catalytic Functionalization of Hexafluoropropene (pages 1818–1822)

      Thomas Braun, Marcel Ahijado Salomon, Kai Altenhöner, Michael Teltewskoi and Silke Hinze

      Version of Record online: 29 JAN 2009 | DOI: 10.1002/anie.200805041

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      Fluorinated building blocks by C[BOND]F bond cleavage: Catalytic C[BOND]F activation reactions that give novel dioxaborolanes have been developed (see scheme). The reactions proceed at room temperature, and catalytic intermediates are presumably rhodium hydride and boryl species.

    17. Medicinal Chemistry

      Drug Delivery by an Enzyme-Mediated Cyclization of a Lipid Prodrug with Unique Bilayer-Formation Properties (pages 1823–1826)

      Lars Linderoth, Günther H. Peters, Robert Madsen and Thomas L. Andresen

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/anie.200805241

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      Special delivery: Liposomal drug-delivery systems in which prodrugs are activated specifically by disease-associated enzymes have great potential for the treatment of severe diseases, such as cancer. A new type of phospholipid-based prodrug has the ability to form stable small unilamellar vesicles (see picture). Activation of the prodrug vesicles by the enzyme sPLA2 initiates a cyclization reaction, which leads to the release of the drug.

    18. Natural Products

      Total Synthesis of Azithromycin (pages 1827–1829)

      Hyoung Cheul Kim and Sung Ho Kang

      Version of Record online: 27 JAN 2009 | DOI: 10.1002/anie.200805334

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      The quaternary king: Azithromycin (1), which has improved pharmacological profiles compared with erythromycins, was the target of an enantioselective synthesis. All the stereogenic quaternary carbon centers were elaborated by a desymmetrization of 2-substituted glycerols using a chiral imine/CuCl2 catalyst.

    19. C[BOND]H Activation

      Room-Temperature Palladium-Catalyzed C[BOND]H Activation: ortho-Carbonylation of Aniline Derivatives (pages 1830–1833)

      Chris E. Houlden, Marc Hutchby, Chris D. Bailey, J. Gair Ford, Simon N. G. Tyler, Michel R. Gagné, Guy C. Lloyd-Jones and Kevin I. Booker-Milburn

      Version of Record online: 23 JAN 2009 | DOI: 10.1002/anie.200805842

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      Pd and CO—ureally got me! The title reaction proceeds efficiently at 18 °C under CO (1 atm) with 5 % [Pd(OTs)2(MeCN)2] as precatalyst. Depending on the solvents used, either anthranilates or cyclic imides can be obtained in high yields (see picture, BQ=benzoquinone, Ts=4-toluenesulfonyl).

    20. Polycarbosilanes

      Radical Polymerization of the Silene (Me3Si)2Si[DOUBLE BOND]CR2 by Hydrogen Transfer from a Trimethylsilyl Group (pages 1834–1837)

      Dmitry Bravo-Zhivotovskii, Semyon Melamed, Victoria Molev, Nadejda Sigal, Boris Tumanskii, Mark Botoshansky, Gregory Molev and Yitzhak Apeloig

      Version of Record online: 2 FEB 2009 | DOI: 10.1002/anie.200805840

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      The silene (Me3Si)2Si[DOUBLE BOND]Ad is polymerized to produce a polycarbosilane with an unusual Si[BOND]Si[BOND]C repeating backbone, rather than the Si[BOND]C or Si[BOND]Si[BOND]C[BOND]C units expected for olefinic radical polymerization. The polymer structure and the polymerization mechanism (see scheme) were studied by GPC, EPR, and NMR spectroscopy and by trapping experiments.

    21. Organocatalysis

      A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric Mannich Reactions of N-Boc-Protected Imines (pages 1838–1840)

      Taichi Kano, Yukako Yamaguchi and Keiji Maruoka

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/anie.200805628

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      The moderate nucleophilicity of the axially chiral amino sulfonamide (S)-1 suppresses the problematic side reactions, including aldol reactions, in the asymmetric Mannich reaction of N-Boc-protected imines with aldehydes. The corresponding adducts are obtained in good yield and excellent stereoselectivity (see scheme; Boc=tert-butoxycarbonyl, Tf=trifluoromethanesulfonyl).

    22. Water Oxidation

      Nanostructured Cobalt Oxide Clusters in Mesoporous Silica as Efficient Oxygen-Evolving Catalysts (pages 1841–1844)

      Feng Jiao and Heinz Frei

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/anie.200805534

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      Light, inexpensive, effective: Nanostructured Co3O4 clusters (see picture) in mesoporous silica are the first example of a nanometer-sized multielectron catalyst made of a first-row transition-metal oxide that evolves oxygen from water efficiently. The nanorod bundle structure of the catalyst results in a very large surface area, an important factor contributing to the high turnover frequency.

    23. Natural Product Synthesis

      An Ugi Reaction in the Total Synthesis of (−)-Dysibetaine (pages 1845–1848)

      Jerry Isaacson and Yoshihisa Kobayashi

      Version of Record online: 27 JAN 2009 | DOI: 10.1002/anie.200805709

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      (−)-Dysibetaine has been synthesized in 11 steps from readily available L-malic acid (see scheme). The key step is a unique Ugi 4-center-3-component cyclization reaction, where an ester group acts as the carboxylic acid component. The use of 1,1,1,3,3,3-hexamethyldisilazane as an ammonia equivalent and a specially designed isocyanide leads to an expeditious synthesis.

    24. Domino Reactions

      Exploiting the Divergent Reactivity of Aryl–Palladium Intermediates for the Rapid Assembly of Fluorene and Phenanthrene Derivatives (pages 1849–1852)

      Ya-Bin Zhao, Brian Mariampillai, David A. Candito, Benoît Laleu, Mengzhou Li and Mark Lautens

      Version of Record online: 28 JAN 2009 | DOI: 10.1002/anie.200805780

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      They all fall down: The value of domino processes can be greatly enhanced when the possibility exists for one to selectively diverge from a common intermediate. In preliminary studies the dual reactivity of aryl–palladium intermediates is exploited. A diverse array of fluorene and phenanthrene derivatives were synthesized in a rapid and efficient manner (see scheme).

    25. Carbohydrate Analogues

      Carbohydrate-2-deoxy-2-phosphonates: Simple Synthesis and Horner–Emmons Reaction (pages 1853–1855)

      Elangovan Elamparuthi and Torsten Linker

      Version of Record online: 23 JAN 2009 | DOI: 10.1002/anie.200804725

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      Phosphorus meets carbohydrates: Dimethyl phosphite reacts with ceric(IV) ammonium nitrate (CAN) to give phosphonyl radicals that add to glycals 1. The derivatives 2 were isolated in high yields and during a subsequent Horner–Emmons reaction underwent an interesting elimination to give 3,6-dihydro-2H-pyrans 3. The short sequence with simple precursors is applicable to the transformation of hexoses, pentoses, and disaccharides. Bn=benzyl.

    26. Natural Products Synthesis

      Total Synthesis of the Antiviral Peptide Antibiotic Feglymycin (pages 1856–1861)

      Frank Dettner, Anne Hänchen, Dominique Schols, Luigi Toti, Antje Nußer and Roderich D. Süssmuth

      Version of Record online: 29 JAN 2009 | DOI: 10.1002/anie.200804130

      Thumbnail image of graphical abstract

      An adaptable approach: The first highly convergent stereoselective synthesis of feglymycin (see structure) and its enantiomer is based on the coupling of repeating peptide fragments. The use of weakly basic conditions throughout the synthesis suppressed the epimerization of sensitive aryl glycine units. Feglymycin has strong anti-HIV activity as well as potent (previously identified as weak) antibacterial activity against Staphylococcus aureus.

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