Angewandte Chemie International Edition

Cover image for Vol. 45 Issue 42

October 27, 2006

Volume 45, Issue 42

Pages 6935–7097

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Book Review
    6. Highlights
    7. Review
    8. Communications
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    1. Cover Picture: Hydrocarbon Uptake in the Alkylated Micropores of a Columnar Supramolecular Solid (Angew. Chem. Int. Ed. 42/2006) (page 6935)

      Thomas J. Taylor, Vladimir I. Bakhmutov and François P. Gabbaï

      Article first published online: 23 OCT 2006 | DOI: 10.1002/anie.200690145

      Alkane storage is generally problematic. Therefore, gases such as ethane, propane, and butane are often burned off in the flares of oil wells and petrochemical plants (cover picture background). A new solid consisting of a hexagonal array of columns and channels (cover picture foreground) reversibly adsorbs short-chain alkanes in its alkylated micropores. In their Communication on page 7030 ff., F. P. Gabbaï and co-workers report its preparation from (HgC6F4)3 and 1,3,5-(Me3SiC[TRIPLE BOND]C)3C6H3, and describe its sorption properties.

  2. Graphical Abstract

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    3. Graphical Abstract
    4. News
    5. Book Review
    6. Highlights
    7. Review
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  3. News

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    4. News
    5. Book Review
    6. Highlights
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  4. Book Review

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    4. News
    5. Book Review
    6. Highlights
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  5. Highlights

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    1. Tsuji–Trost Allylic Alkylation with Ketone Enolates (pages 6952–6955)

      Manfred Braun and Thorsten Meier

      Article first published online: 9 OCT 2006 | DOI: 10.1002/anie.200602169

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      The traditional restriction of the palladium-catalyzed allylation to stabilized carbanions has been overcome. Recent studies reveal that preformed “hard” enolates can serve as nucleophiles, and routes to novel stereoselective variants of the Tsuji–Trost method have thus been opened.

    2. An FeVI Nitride: There Is Plenty of Room at the Top! (pages 6956–6959)

      Paul J. Chirik

      Article first published online: 9 OCT 2006 | DOI: 10.1002/anie.200603056

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      Movin' on up: Recent developments in the coordination chemistry of high-oxidation-state iron nitrido compounds are highlighted. Special attention is devoted to a newly synthesized FeVI compound (see scheme), only the second known example of a hexavalent iron complex.

  6. Review

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    1. Hydrogen Peroxide Synthesis: An Outlook beyond the Anthraquinone Process (pages 6962–6984)

      Jose M. Campos-Martin, Gema Blanco-Brieva and Jose L. G. Fierro

      Article first published online: 13 OCT 2006 | DOI: 10.1002/anie.200503779

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      The industrial synthesis of hydrogen peroxide by the anthraquinone process requires multiple unit operations and bears several disadvantages, such as the generation of by-products and significant energy requirements. Thus, the direct synthesis of hydrogen peroxide from H2 and O2 (for example, with the aid of a Pd catalyst, see scheme) is a chemically and technologically significant alternative.

  7. Communications

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    1. A Bifunctional Molecularly Imprinted Polymer (MIP): Analysis of Binding and Catalysis by a Thermistor (pages 6986–6990)

      Kristian Lettau, Axel Warsinke, Martin Katterle, Bengt Danielsson and Frieder W. Scheller

      Article first published online: 23 OCT 2006 | DOI: 10.1002/anie.200601796

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      Binding or catalysis? Both can be distinguished with a molecularly imprinted polymer (MIP) by the different patterns of heat generation. The catalytically active sites, like in the corresponding enzyme, generate a steady-state temperature increase. Thus, enzyme-like catalysis and antibody-analogue binding are analyzed simultaneously in a bifunctional MIP for the first time (see scheme).

    2. Enantioselective Total Synthesis and Structure Determination of the Antiherpetic Anthrapyran Antibiotic AH-1763 IIa (pages 6990–6993)

      Lutz F. Tietze, Kersten M. Gericke and Ramakrishna Reddy Singidi

      Article first published online: 29 SEP 2006 | DOI: 10.1002/anie.200601992

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      The antiherpetic anthrapyran antibiotic (14S,16R)-AH-1763 IIa (see right-hand structure) and its (14R,16R) diastereomer have been prepared in enantioselective total syntheses. The relative and absolute stereochemistry of the natural product was established as (14R,16S), and a general high-yielding, selective approach to anthrapyran antibiotics was developed.

    3. TiO2–Nb2O5 Nanotubes with Electrochemically Tunable Morphologies (pages 6993–6996)

      Andrei Ghicov, Saule Aldabergenova, Hiroaki Tsuchyia and Patrik Schmuki

      Article first published online: 29 SEP 2006 | DOI: 10.1002/anie.200601957

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      Made to measure: TiO2–Nb2O5 nanotubes are grown on a Ti–Nb alloy (Ti45Nb) by anodization in a fluoride-containing electrolyte (see micrograph), and their lengths and diameters can be controlled by adjusting the potential. The low rate of chemical dissolution of Nb2O5 in the electrolyte allows the formation of long nanotubes with regular morphology.

    4. AgOC(CF3)3 and AgOSiiPr3—Synthesis and Characterization of a Donor-Free Silver(I) Alkoxide and Silyl Oxide (pages 6997–7000)

      Andreas Reisinger, Daniel Himmel and Ingo Krossing

      Article first published online: 22 SEP 2006 | DOI: 10.1002/anie.200600805

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      Over 30 years after the first successful syntheses of CuI alkoxides and silyl oxides, the first homologous AgI compounds were synthesized and characterized (see scheme). AgOC(CF3)3 was furthermore found to be a promising precursor for chemical vapor deposition processes and the deposition of AgF.

    5. Microreactor Synthesis of β-Peptides (pages 7000–7003)

      Oliver Flögel, Jeroen D. C. Codée, Dieter Seebach and Peter H. Seeberger

      Article first published online: 29 SEP 2006 | DOI: 10.1002/anie.200602167

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      Taming the insoluble: The reaction parameters of a β-peptide synthesis were optimized using only small amounts of reagents in a silicon microreactor (see picture). The use of unusually high temperatures (up to 120 °C) reduces the reaction times. The insertion of a fluorous benzyl protecting group enhances the efficiency of the synthesis.

    6. Kinetic Resolution of 4-Hydroxy-2-ketones Catalyzed by a Baeyer–Villiger Monooxygenase (pages 7004–7006)

      Anett Kirschner and Uwe T. Bornscheuer

      Article first published online: 2 OCT 2006 | DOI: 10.1002/anie.200602986

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      Two with one stroke: The kinetic resolution of racemic 4-hydroxy-2-ketones catalyzed by Baeyer–Villiger monooxygenase (BVMO) afforded not only the unreacted enantiomer in good optical purity but also allows access to optically active 1,2-diols (see scheme). Thus, this enzymatic approach provides a range of products in a single reaction accessible otherwise only from reactions with ketoreductases and hydrolases.

    7. You have free access to this content
      The Two Odors of Iron when Touched or Pickled: (Skin) Carbonyl Compounds and Organophosphines (pages 7006–7009)

      Dietmar Glindemann, Andrea Dietrich, Hans-Joachim Staerk and Peter Kuschk

      Article first published online: 28 SEP 2006 | DOI: 10.1002/anie.200602100

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      The smell of money and chemical weapons: The perplexing metallic odor from touching iron tools or coins (see picture) is a type of human body odor linked to the decomposition of skin peroxides. Fe2+ ion containing rust, drinking water, and blood all cause a similar metallic odor. Another “garlic” metallic odor, that of phosphorus-alloyed iron under acid attack, is caused by organophosphines, including C–P compounds which are monitored under the Chemical Weapons Convention.

    8. Structure–Activity Relationships in Chromatography: Retention Prediction of Oligonucleotides with Support Vector Regression (pages 7009–7012)

      Oliver Kohlbacher, Sascha Quinten, Marc Sturm, Bettina M. Mayr and Christian G. Huber

      Article first published online: 29 SEP 2006 | DOI: 10.1002/anie.200602561

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      Secondary structures of biopolymers have a significant influence on their molecular interactions with surfaces. With the aid of machine learning through support vector regression, the retention of oligonucleotides was modeled in ion-pair reversed-phase chromatography with high prediction accuracy (see diagram).

    9. Charge-Induced Molecular Alignment of Intrinsically Disordered Proteins (pages 7012–7015)

      Lukasz Skora, Min-Kyu Cho, Hai-Young Kim, Stefan Becker, Claudio O. Fernandez, Martin Blackledge and Markus Zweckstetter

      Article first published online: 28 SEP 2006 | DOI: 10.1002/anie.200602317

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      NMR dipolar couplings are a sensitive spectroscopic probe of the structure and dynamics of biomolecules. It is demonstrated that molecular alignment of intrinsically disordered proteins depends critically on electrostatic interactions, is scaled with the ionic strength of the solution, and can be predicted by using a simplified electrostatic model.

    10. Photocontrolled Folding and Unfolding of a Collagen Triple Helix (pages 7015–7018)

      Ulrike Kusebauch, Sergio A. Cadamuro, Hans-Jürgen  Musiol, Martin O. Lenz, Josef Wachtveitl, Luis Moroder and Christian Renner

      Article first published online: 28 SEP 2006 | DOI: 10.1002/anie.200601432

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      At the flick of a switch: Two side chains of a collagen peptide containing (2S,4S)-mercaptoproline at two defined positions are linked with a diiodo azobenzene derivative. With the trans isomer of the azobenzene clamp (orange), the peptide folds into the collagen triple helix (green, blue, gray), which unfolds upon irradiation at 330 nm. The light-controlled folding/unfolding processes are fully reversible, making this system well-suited for ultrafast spectroscopic analysis.

    11. Cocrystallization and Encapsulation of a Fluorophore with Hexameric Pyrogallol[4]arene Nanocapsules: Structural and Fluorescence Studies (pages 7019–7022)

      Scott J. Dalgarno, Daniel B. Bassil, Sheryl A. Tucker and Jerry L. Atwood

      Article first published online: 2 OCT 2006 | DOI: 10.1002/anie.200601961

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      Throwing light on encapsulation: The fluorescent probe molecule 4-[3-(9-anthryl)propyl]-N,N-dimethylaniline (C gray, N blue) crystallizes either exo or endo to the cavity of pyrogallol[4]arene hexamers (O red) and displays markedly different fluorescence emission behavior as a result. In the exo array, the guest alters the packing of the hexamer by forming channels through the extended structure in the solid state (see picture).

    12. Octameric and Decameric Aluminophosphates (pages 7022–7026)

      Ramaswamy Murugavel and Subramaniam Kuppuswamy

      Article first published online: 2 OCT 2006 | DOI: 10.1002/anie.200601979

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      Big Al: The title compounds are not only among the largest molecular aluminophosphates synthesized thus far, but are also rare polyhedral cages that contain AlO4, AlO5, and AlO6 coordination geometries (see structure; red O, blue Al, pink P). The cores of these aluminophosphates represent new structural building units (SBUs) in zeolite chemistry.

    13. Fluorescent H-Aggregates of Merocyanine Dyes (pages 7026–7030)

      Ulrich Rösch, Sheng Yao, Rüdiger Wortmann and Frank Würthner

      Article first published online: 2 OCT 2006 | DOI: 10.1002/anie.200602286

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      Unexpected lighting up: A slight rotational twist and rigidification of merocyanine dyes in a face-to-face π-π-stacked dimer aggregate resulted in an unexpected increase in the fluorescence intensity and lifetime (see graph). This result contrasts the common perception that the fluorescence of H-aggregates is strongly quenched, but can be rationalized within the concept of exciton theory.

    14. Hydrocarbon Uptake in the Alkylated Micropores of a Columnar Supramolecular Solid (pages 7030–7033)

      Thomas J. Taylor, Vladimir I. Bakhmutov and François P. Gabbaï

      Article first published online: 29 AUG 2006 | DOI: 10.1002/anie.200602440

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      Neither Doric, Ionic, nor Corinthian! (HgC6F4)3 interacts with 1,3,5-(Me3SiC[TRIPLE BOND]C)3C6H3 to form columns with peripheral trimethylsilyl groups. These columns self-aggregate into a hexagonal solid containing pores lined by nonpolar methyl groups (see picture; Hg orange, Si purple, C gray, F green, H white), which can adsorb alkanes reversibly.

    15. Calculation of the Dependence of Homo- and Heteronuclear 3J and 2J Scalar Couplings for the Determination of the 2′-Hydroxy Conformation in RNA (pages 7033–7036)

      Jörg Fohrer, Uwe Reinscheid, Mirko Hennig and Teresa Carlomagno

      Article first published online: 27 SEP 2006 | DOI: 10.1002/anie.200602583

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      Packing a punch: The 2′-hydroxy group has a strong effect on the structural and dynamic properties of RNA and DNA, and governs the hydration of the RNA minor groove. The conformation of this group was previously investigated using NOEs and 2J(C2′,OH2) and 3J(C1′/C3′/H2′,OH2) couplings at low temperature in water. In the present study, ab initio calculations were used to derive appropriate Karplus-like equations for the couplings (see picture).

    16. Formation and Structure of a Stable Monoradical Cation by Reduction of a Diphosphafulvenium Salt (pages 7036–7039)

      Frédéric Biaso, Thibault Cantat, Nicolas Mézailles, Louis Ricard, Pascal Le Floch and Michel Geoffroy

      Article first published online: 2 OCT 2006 | DOI: 10.1002/anie.200603009

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      One-electron reduction of a diphosphafulvenium dication gives the first stable diphosphafulvenium monoradical cation (see scheme). An X-ray crystal structure analysis, EPR measurements, and DFT calculations clearly show that reduction takes place at the exocyclic double bond and that the excess of electron density is stabilized by the two electron-withdrawing phosphonium groups (see SOMO; P orange, C dark gray, H light gray).

    17. One-Step, Confined Growth of Bimetallic Tin–Antimony Nanorods in Carbon Nanotubes Grown In Situ for Reversible Li+ Ion Storage (pages 7039–7042)

      Yong Wang and Jim Yang Lee

      Article first published online: 29 SEP 2006 | DOI: 10.1002/anie.200602071

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      Two into one does go: A high-yield preparation of carbon nanotube (CNT)-encapsulated Sn–Sb nanorods that exhibit excellent lithium storage properties is described. The perceived growth process involves a) antimony tin oxide nanoparticles, b) growth of carbon nanotubes induced by molten Sn–Sb alloy, and c) capillary encapsulation of molten Sn–Sb into carbon-nanotube interior (see scheme).

    18. Electrochemical Switching and Size Selection in Cucurbit[8]uril-Mediated Dendrimer Self-Assembly (pages 7042–7046)

      Wei Wang and Angel E. Kaifer

      Article first published online: 2 OCT 2006 | DOI: 10.1002/anie.200602220

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      A host of possibilities: Cucurbit[8]uril acts as a host to mediate in a highly effective way the formation of charge-transfer complexes between dendrimers containing accessible π-donor and π-acceptor units (see scheme). Redox switching of the self-assembly affords control over the size of the predominant dendrimer assemblies.

    19. A Simple Rule of Thumb for Diffusion on Transition-Metal Surfaces (pages 7046–7049)

      Anand Udaykumar Nilekar, Jeff Greeley and Manos Mavrikakis

      Article first published online: 29 SEP 2006 | DOI: 10.1002/anie.200602223

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      On the surface: Diffusion on transition-metal surfaces plays a key role in the transport of atomic and molecular species on catalytic surfaces. Density functional calculations show that there is a simple linear relation that allows the prediction of the diffusion barrier from the binding energy of the diffusing species on the respective metal surface.

    20. The Question of the Cr Oxidation State in the {Cr(SNS)} Catalyst for Selective Ethylene Trimerization: An Unanticipated Re-Oxidation Pathway (pages 7050–7053)

      Claire Temple, Amir Jabri, Patrick Crewdson, Sandro Gambarotta, Ilia Korobkov and Robbert Duchateau

      Article first published online: 28 SEP 2006 | DOI: 10.1002/anie.200602240

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      An unprecedented oxidation of chromium(II) by trimethylaluminum which, despite the reducing environment, forms a cationic organochromium(III) complex (see picture; SNS=RSCH2CH2N(H)CH2CH2SR, Cy=cyclohexyl, X=[Me6Al2Cl]), provides a possible catalyst re-activation pathway.

    21. Hierarchical Growth of Large-Scale Ordered Zeolite Silicalite-1 Membranes with High Permeability and Selectivity for Recycling CO2 (pages 7053–7056)

      Hailing Guo, Guangshan Zhu, Hua Li, Xiaoqin Zou, Xiaoju Yin, Weishen Yang, Shilun Qiu and Ruren Xu

      Article first published online: 2 OCT 2006 | DOI: 10.1002/anie.200602308

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      Another fine mesh you've got me into: A stainless-steel-net-imbedded silicalite-1 membrane (MFI film) is synthesized by a hydrothermal method. A hierarchical growth mechanism of the membrane formation is deduced. The MFI film has high thermal and mechanical stability, large-scale order, and exhibits high permeation flux and excellent permeation selectivity for CO2 (see scheme).

    22. Efficient Phosphodiester Binding and Cleavage by a ZnII Complex Combining Hydrogen-Bonding Interactions and Double Lewis Acid Activation (pages 7056–7059)

      Guoqiang Feng, Daniela Natale, Ravi Prabaharan, Juan C. Mareque-Rivas and Nicholas H. Williams

      Article first published online: 29 SEP 2006 | DOI: 10.1002/anie.200602532

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      A combined attack: Hydrogen-bonding interactions with double Lewis acid activation generate a dinuclear ZnII complex that is exceptionally effective for binding monoanionic phosphate diesters in water and for catalyzing phosphodiester transesterifications. The complex catalyzes the hydrolytic cleavage of RNA-like activated, artificial substrates and nonactivated, natural substrates with similar efficiencies.

    23. Single-Step Synthesis and Surface-Assisted Growth of Superconducting TaS2 Nanowires (pages 7060–7063)

      Charles W. Dunnill, Hannah K. Edwards, Paul D. Brown and Duncan H. Gregory

      Article first published online: 28 SEP 2006 | DOI: 10.1002/anie.200602614

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      Super skinny: TaS2 nanowires with a high aspect ratio (50 000:1; see micrograph) are synthesized from the elements in a one-step reaction. The single-crystalline 2H-TaS2 nanowires are superconducting, with a transition temperature (Tc=3.4 K) that is enhanced compared to that of the bulk material (Tc=0.8 K).

    24. Ligand-Free Platinum Nanoparticles Encapsulated in a Hollow Porous Carbon Shell as a Highly Active Heterogeneous Hydrogenation Catalyst (pages 7063–7066)

      Shigeru Ikeda, Satoru Ishino, Takashi Harada, Natsumi Okamoto, Takao Sakata, Hirotaro Mori, Susumu Kuwabata, Tsukasa Torimoto and Michio Matsumura

      Article first published online: 28 SEP 2006 | DOI: 10.1002/anie.200602700

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      Wrapped up but still active: A platinum nanoparticle that is 2.2 nm in diameter and not coated by any stabilizing agent can be encapsulated in a hollow carbon shell 30–40 nm in diameter with a micro- to nanoporous wall structure (see picture). This encapsulated nanoparticle acts as an efficient and recyclable heterogeneous catalyst for various liquid-phase hydrogenation reactions.

    25. The Use of Vinyl Sulfonium Salts in the Stereocontrolled Asymmetric Synthesis of Epoxide- and Aziridine-Fused Heterocycles: Application to the Synthesis of (−)-Balanol (pages 7066–7069)

      Matthew G. Unthank, Nigel Hussain and Varinder K. Aggarwal

      Article first published online: 29 SEP 2006 | DOI: 10.1002/anie.200602782

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      Lift your ylides: An asymmetric, epoxy-annulation reaction mediated by a vinyl sulfonium salt converts aminoaldehydes and -ketones into fused heterocyclic epoxides. The methodology was extended to an aziridine-annulation reaction, which was used to complete the shortest known formal synthesis of balanol (see scheme, Ts=toluene-p-sulfonyl, Tf=trifluoromethanesulfonyl).

    26. A Rearrangement to a Zirconium–Alkenylidene in the Insertion of Dihalocarbenoids and Acetylides into Zirconacycles (pages 7070–7072)

      Emma Thomas, Sally Dixon and Richard J Whitby

      Article first published online: 29 SEP 2006 | DOI: 10.1002/anie.200602822

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      Sequential insertion of 1-lithio-1,1-dihaloalkanes and lithium acetylides into zirconacyclopentenes and -pentanes affords complex bicyclo[3.3.0]octenes and bicyclo[3.3.0]octanes through a novel rearrangement of a zirconium–alkynyl to a zirconate—alkenylidene species (see scheme; Cp=cyclopentadienyl).

    27. Total Synthesis of IKD-8344 (pages 7072–7075)

      Woo Han Kim, Sung Kil Hong, Sang Min Lim, Min-Ae Ju, Soon Kyu Jung, Yong Wook Kim, Jae Hoon Jung, Min Sang Kwon and Eun Lee

      Article first published online: 2 OCT 2006 | DOI: 10.1002/anie.200602860

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      Complete construction: The total synthesis of IKD-8344, a novel 28-membered ring macrodiolide antibiotic (see structure), was accomplished by employing Williamson ether synthesis, β-alkoxymethacrylate radical cyclization, and Yamaguchi lactonization reactions. This synthesis is another example of the application of β-alkoxymethacrylate radical cyclization reactions for the stereoselective construction of complex oxacyclic natural products.

    28. A Pathway for NH Addition to Styrene Promoted by Gold (pages 7075–7078)

      Xingyi Deng, Thomas A. Baker and Cynthia M. Friend

      Article first published online: 2 OCT 2006 | DOI: 10.1002/anie.200602876

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      Going for gold! The synthesis of aziridines using heterogeneous gold catalysts has an unanticipated potential. Chemisorbed atomic oxygen is used to activate ammonia, producing NH bound to the gold surface (see scheme). Addition of NH across the double bond of styrene gave 2-phenylaziridine on a single-crystal Au(111) surface.

    29. Domino Cu-Catalyzed C[BOND]N Coupling/Hydroamidation: A Highly Efficient Synthesis of Nitrogen Heterocycles (pages 7079–7082)

      Rubén Martín, Marta Rodríguez Rivero and Stephen L. Buchwald

      Article first published online: 29 SEP 2006 | DOI: 10.1002/anie.200602917

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      Working in tandem: Highly functionalized pyrroles and pyrazoles can be synthesized from a domino Cu-catalyzed C[BOND]N coupling/hydroamidation sequence. The scope and the generality of the method is noteworthy as a wide variety of substituents, either in the alkene or alkyne counterparts, are well tolerated.

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      Intermolecular Oxidative Enolate Heterocoupling (pages 7083–7086)

      Phil S. Baran and Michael P. DeMartino

      Article first published online: 29 SEP 2006 | DOI: 10.1002/anie.200603024

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      No priming necessary: The intermolecular oxidative heterocoupling of imides and oxindoles to esters, ketones, and lactones is shown for the first time to be synthetically viable. Strategic use of the initial oxidation state of the reactants allows for the excision of prefunctionalization steps (halogenation, enol-silane formation) and allows for the concise synthesis of unsymmetrical lignans, such as (−)-bursehernin (1).

    31. Total Synthesis of Platensimycin (pages 7086–7090)

      K. C. Nicolaou, Ang Li and David J. Edmonds

      Article first published online: 29 SEP 2006 | DOI: 10.1002/anie.200603892

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      Beat the superbugs: The newly discovered antibiotic platensimycin (1) promises to combat current drug-resistant infections. The natural product shows potent activity against Gram-positive bacteria and contains a novel molecular architecture. The total synthesis of this intriguing natural product that opens the way to a variety of otherwise inaccessible analogues has now been achieved (calculated structure shown on the right).

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    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Book Review
    6. Highlights
    7. Review
    8. Communications
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    1. You have free access to this content
      Preview: Angew. Chem. Int. Ed. 42/2006 (page 7097)

      Article first published online: 23 OCT 2006 | DOI: 10.1002/anie.200690147

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