Angewandte Chemie International Edition

Cover image for Vol. 47 Issue 7

February 1, 2008

Volume 47, Issue 7

Pages 1153–1339

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Cover Picture: Chemistry and Biology of the Aeruginosin Family of Serine Protease Inhibitors (Angew. Chem. Int. Ed. 7/2008) (page 1153)

      Karolina Ersmark, Juan R. Del Valle and Stephen Hanessian

      Version of Record online: 25 JAN 2008 | DOI: 10.1002/anie.200890018

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      Different phyla and different oceans are sources of linear peptides in the aeruginosin family which comprise a central hydroxy- (or dihydroxy-) octahydroindole carboxamide core unit onto which unusual amino acids are appended. The aeruginosins exhibit varying degrees of inhibitory activity against serine proteases, including factor II (thrombin) and factor VIIa of the blood coagulation cascade. In their Review on page 1202 ff., S. Hanessian et al. provide an overview of the chemical and biological properties of the aeruginosins as well as the natural sources of these compounds, their total syntheses, and structure revisions.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Inside Cover: Oxidative Cross-Coupling of Arenes Induced by Single-Electron Transfer Leading to Biaryls by Use of Organoiodine(III) Oxidants (Angew. Chem. Int. Ed. 7/2008) (page 1154)

      Toshifumi Dohi, Motoki Ito, Koji Morimoto, Minako Iwata and Yasuyuki Kita

      Version of Record online: 25 JAN 2008 | DOI: 10.1002/anie.200890019

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      Environmentally friendly iodine(III) reagents can induce selective activation of naphthalene derivatives by a unique single-electron transfer (SET) mechanism. In their Communication on page 1301 ff., Y. Kita and co-workers describe the successful oxidative cross-coupling of unfunctionalized arenes using organoiodine(III) oxidants without need of metal catalysts. The picture emphasizes the flow of the single electrons from the hypervalent iodine(III) reagents and the green nature of the transformation.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Obituary
    8. Book Review
    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. Obituary
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. You have free access to this content
      Conjugated Microporous Poly(aryleneethynylene) Networks (page 1167)

      Jia-Xing Jiang, Fabing Su, Abbie Trewin, Colin D. Wood, Neil L. Campbell, Hongjun Niu, Calum Dickinson, Alexey Y. Ganin, Matthew J. Rosseinsky, Yaroslav Z. Khimyak and Andrew I. Cooper

      Version of Record online: 25 JAN 2008 | DOI: 10.1002/anie.200890021

      This article corrects:

      Conjugated Microporous Poly(aryleneethynylene) Networks1

      Vol. 46, Issue 45, 8574–8578, Version of Record online: 26 SEP 2007

  5. News

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

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Obituary
    8. Book Review
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    10. Minireview
    11. Review
    12. Communications
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    1. Arthur Kornberg (1918–2007) (page 1172)

      Ulrich Hübscher

      Version of Record online: 25 JAN 2008 | DOI: 10.1002/anie.200705248

  7. Book Review

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Obituary
    8. Book Review
    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. Obituary
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
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    1. The Catalytic Asymmetric Strecker Reaction: Ketimines Continue to Join the Fold (pages 1176–1178)

      Stephen J. Connon

      Version of Record online: 3 JAN 2008 | DOI: 10.1002/anie.200703879

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      Picking up the gauntlet: The challenge of developing highly effective catalyst systems for the enantioselective Strecker reaction to convert ketimine substrates (see scheme, red; A denotes protecting group) into α-amino nitriles (blue) and ultimately α-amino acids has been met by several recent developments.

    2. Catalytic Asymmetric Fluorination Comes of Age (pages 1179–1182)

      Vincent A. Brunet and David O'Hagan

      Version of Record online: 27 DEC 2007 | DOI: 10.1002/anie.200704700

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      Gimme an F: Ever since the first asymmetric fluorination reagents were reported in 1988, the enantioselective introduction of a C[BOND]F bond at a stereogenic center has emerged as a major objective in organic chemistry. Newly published results on the enantioselective fluorination of malonates (see scheme) are put into context in this Highlight. NFSI=N-fluorodibenzenesulfonimide.

  9. Minireview

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
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    1. The Chemistry of Fluorescent Bodipy Dyes: Versatility Unsurpassed (pages 1184–1201)

      Gilles Ulrich, Raymond Ziessel and Anthony Harriman

      Version of Record online: 18 DEC 2007 | DOI: 10.1002/anie.200702070

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      Unexpected adaptability: The properties of dipyrrometheneboron difluoride (F-Bodipy) dyes can be modified in many ways (see picture, B pink, N blue, C gray). This versatility has allowed new uses to be developed for this molecule. Emphasis is given to synthetic considerations, optical properties, and applications as chemical sensors, luminescent devices, and molecular materials.

  10. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Chemistry and Biology of the Aeruginosin Family of Serine Protease Inhibitors (pages 1202–1223)

      Karolina Ersmark, Juan R. Del Valle and Stephen Hanessian

      Version of Record online: 12 DEC 2007 | DOI: 10.1002/anie.200605219

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      Oceans apart: With sources ranging from the marine sponges in North Queensland, Australia, to the cyanobacterial waterblooms of Lake Kasumigaura, Japan, and the blue-green algae found in Hula Valley, Israel, the aeruginosin family of linear peptides exhibit potent inhibition against serine proteases such as the medically relevant thrombin, as well as other proteins involved in the blood coagulation cascade.

  11. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Structure of the Tyrosyl Biradical in Mouse R2 Ribonucleotide Reductase from High-Field PELDOR (pages 1224–1227)

      Vasyl P. Denysenkov, Daniele Biglino, Wolfgang Lubitz, Thomas F. Prisner and Marina Bennati

      Version of Record online: 2 JAN 2008 | DOI: 10.1002/anie.200703753

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      Paramagnetic centers rigidly embedded in proteins serve as a probe in structural studies of macromolecular complexes. Pulse EPR at high frequencies allows the determination of not only the distance but also the relative orientation of these centers (see tyrosyl radicals; C gray, O red, N blue). The method has considerable potential for studying the assembly of protein complexes.

    2. Reversible Electron Transfer Coupled to Spin Crossover in an Iron Coordination Salt in the Solid State (pages 1228–1231)

      Marat M. Khusniyarov, Thomas Weyhermüller, Eckhard Bill and Karl Wieghardt

      Version of Record online: 4 JAN 2008 | DOI: 10.1002/anie.200704951

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      A rad. dad: The electronic structure of [Fe(dad)3][Fe(pda)2] was investigated by X-ray crystallography, Mössbauer spectroscopy, and magnetic susceptibility measurements as a function of the temperature. Reversible one-electron transfer from the dianion (high-spin FeII) to the dication (low-spin FeII) generates a monoanion (intermediate-spin FeIII) and a monocation (high-spin FeII and α-diimine π radical anion) above 235 K.

    3. Evolution of Homochiral Helical Dye Assemblies: Involvement of Autocatalysis in the “Majority-Rules” Effect (pages 1232–1236)

      Andreas Lohr and Frank Würthner

      Version of Record online: 8 JAN 2008 | DOI: 10.1002/anie.200704550

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      Chiral amplification in action: Kinetic studies on the self-assembly of bis(merocyanine) dyes reveal that two phenomena that have been suggested to be of importance for natural homochirogenesis, namely, autocatalysis and the “majority-rules” effect, are both involved in the evolution of homochiral helical dye nanorods (see picture, D=supramolecular oligomer species; H1=kinetically self-assembled nanorods; H1*=H1-type aggregate precursors).

    4. Photoisomerization of cis,cis- and cis,trans-1,4-Di-o-tolyl-1,3-butadiene in Glassy Media at 77 K: One-Bond-Twist and Bicycle-Pedal Mechanisms (pages 1237–1240)

      Jack Saltiel, Michael A. Bremer, Somchoke Laohhasurayotin and Tallapragada S. R. Krishna

      Version of Record online: 4 JAN 2008 | DOI: 10.1002/anie.200704465

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      Let's twist again: In the isomerization of cis,cis-1,4-di-o-tolyl-1,3-butadiene in isopentane glass at 77 K, hula-twist pathways are eliminated, because unstable photoproduct conformers do not form. Instead, the isomerization is found to proceed by bicycle-pedal (BP) and one-bond-twist (OBT) mechanisms (see scheme).

    5. Nanofibers and Lyotropic Liquid Crystals from a Class of Self-Assembling β-Peptides (pages 1241–1244)

      William C. Pomerantz, Virany M. Yuwono, Claire L. Pizzey, Jeffery D. Hartgerink, Nicholas L. Abbott and Samuel H. Gellman

      Version of Record online: 8 JAN 2008 | DOI: 10.1002/anie.200704372

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      More than a pretty phase: A class of helical β-peptides has been discovered that form lyotropic liquid-crystalline (LC) phases in water. The β-peptide sequence strongly affects the mode of assembly and ultimately whether a LC phase is formed. For a non-globally amphiphilic β-peptide that can form a LC phase, cryo-TEM revealed thin fibers several micrometers in length, consistent with Onsager theory.

    6. Self-Assembly of a Homochiral Nanoscale Metallacycle from a Metallosalen Complex for Enantioselective Separation (pages 1245–1249)

      Gao Li, Weibin Yu, Jia Ni, Taifeng Liu, Yan Liu, Enhong Sheng and Yong Cui

      Version of Record online: 4 JAN 2008 | DOI: 10.1002/anie.200704347

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      Only half may enter: A homochiral porous nanoscale metallacycle has been efficiently self-assembled from semiflexible enantiopure metallosalen complexes with complementary coordination motifs. Single crystals of the macromolecule (see structure; C gray, Zn purple, O red, N blue) show a reversible and controllable dynamic behavior. Particularly, the metallacycle can be used to resolve small racemic alcohols with high enantioselectivity (over 99.0 % ee).

    7. Antibacterial and Hemolytic Activities of Pyridinium Polymers as a Function of the Spatial Relationship between the Positive Charge and the Pendant Alkyl Tail (pages 1250–1254)

      Varun Sambhy, Blake R. Peterson and Ayusman Sen

      Version of Record online: 7 JAN 2008 | DOI: 10.1002/anie.200702287

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      The benefits of separation: For homologous polymers having similar backbone composition and charge/tail ratios, placing the charge and alkyl tail on spatially separated centers results in a higher membrane-disrupting ability, as evident from the increased antibacterial and hemolytic activities. The spatial separation particularly amplifies mammalian cell toxicity (see picture).

    8. Synthesis and Lithographic Patterning of FePt Nanoparticles Using a Bimetallic Metallopolyyne Precursor (pages 1255–1259)

      Kun Liu, Cheuk-Lam Ho, Stephane Aouba, Yi-Qun Zhao, Zheng-Hong Lu, Srebri Petrov, Neil Coombs, Paul Dube, Harry E. Ruda, Wai-Yeung Wong and Ian Manners

      Version of Record online: 3 JAN 2008 | DOI: 10.1002/anie.200703199

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      Micropatterns of arrays of ferromagnetic face-centered tetragonal FePt nanoparticles can be fabricated from thin films of a novel air- and moisture-stable bimetallic polyferroplatinyne precursor, which can be utilized directly as a negative resist in both electron-beam lithography and UV photolithography.

    9. Virion-Mimicking Nanocapsules from pH-Controlled Hierarchical Self-Assembly for Gene Delivery (pages 1260–1264)

      Peisheng Xu, Shi-Yan Li, Qun Li, Edward A. Van Kirk, Jun Ren, William J. Murdoch, Zhaojie Zhang, Maciej Radosz and Youqing Shen

      Version of Record online: 8 JAN 2008 | DOI: 10.1002/anie.200703203

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      A new concept for fabricating nanocarriers carrying free DNA for gene delivery to overcome the intracellular dissociation barrier of cationic polymer/DNA complexes is presented. Free DNA plasmids (shown in green) are encapsulated in a nanocapsule core, which is protected by a hydrophobic membrane (purple) with a poly(ethylene glycol) outer layer (blue). The nanocapsules can release free DNA into the cells and have high in vitro and in vivo transfection efficiency.

    10. Differentiation between Structurally Homologous Shiga 1 and Shiga 2 Toxins by Using Synthetic Glycoconjugates (pages 1265–1268)

      Ramesh R. Kale, Colleen M. McGannon, Cynthia Fuller-Schaefer, Duane M. Hatch, Michael J. Flagler, Shantini D. Gamage, Alison A. Weiss and Suri S. Iyer

      Version of Record online: 2 JAN 2008 | DOI: 10.1002/anie.200703680

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      Choose your poison: Shiga toxins 1 and 2 are the major virulence factors of E. coli O157:H7. However, Shiga 2 is more potent than Shiga 1. Biotinylated glycoconjugates have been developed that differentiate between these structurally homologous toxins (see picture; R=OH: selective for Shiga 1; R=NHAc: selective for Shiga 2). These synthetic materials efficiently capture toxins without interference from the sample matrix.

    11. A Selective Instant Synthesis of a Coordination Network and Its Ab Initio Powder Structure Determination (pages 1269–1271)

      Masaki Kawano, Tsuyoshi Haneda, Daisuke Hashizume, Fujio Izumi and Makoto Fujita

      Version of Record online: 8 JAN 2008 | DOI: 10.1002/anie.200704809

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      Fast powders and slow crystals: A uniform powder sample of a flexible porous coordination network is prepared in high yield by kinetically controlled synthesis and its crystal structure solved by synchrotron ab initio powder X-ray diffraction (see picture). Crystals of a totally different porous network with larger channels for guest encapsulation are also obtained by thermodynamic control in a slow crystallization process.

    12. Total Synthesis of Ouabagenin and Ouabain (pages 1272–1275)

      Hongxing Zhang, Maddi Sridhar Reddy, Serge Phoenix and Pierre Deslongchamps

      Version of Record online: 8 JAN 2008 | DOI: 10.1002/anie.200704959

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      The highly oxygenated steroid ouabagenin (1 b) and its glycoside ouabain (1 a) were prepared by a strategy based on a polyanionic cyclization. Starting building blocks A and B were combined to give the key intermediate C and transformed into 1 b in 27 steps. Finally, ouabagenin (1 b) was converted into ouabain (1 a) in six steps (see scheme).

    13. Dissociation Behavior of Clathrate Hydrates to Ice and Dependence on Guest Molecules (pages 1276–1279)

      Satoshi Takeya and John A. Ripmeester

      Version of Record online: 8 JAN 2008 | DOI: 10.1002/anie.200703718

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      Self-preservation: The existence of gas hydrates (see picture) outside their stability zone for prolonged periods is shown to depend on the interaction strength between guest molecules (red) and water (blue), as reflected by the dissociation pressures at 273 K.

    14. Palladium–(S,pR)-FerroNPS-Catalyzed Asymmetric Allylic Etherification: Electronic Effect of Nonconjugated Substituents on Benzylic Alcohols on Enantioselectivity (pages 1280–1283)

      Fuk Loi Lam, Terry Tin-Lok Au-Yeung, Fuk Yee Kwong, Zhongyuan Zhou, Kwok Yin Wong and Albert S. C. Chan

      Version of Record online: 3 JAN 2008 | DOI: 10.1002/anie.200703955

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      An enantioselective C[BOND]O bond-forming reaction proceeds well under palladium catalysis with newly developed N–P,S ligands with a ferrocene motif (see scheme). Nonconjugated substituents on the benzylic alcohol substrate lead to an increase in enantioselectivity with increasing electron-donating ability in the title reaction with racemic 1,3-diphenyl-2-propenyl acetate. Cy = cyclohexyl.

    15. Enantioselective Synthesis of (+)-Monobromophakellin and (+)-Phakellin: A Concise Phakellin Annulation Strategy Applicable to Palau'amine (pages 1284–1286)

      Shaohui Wang and Daniel Romo

      Version of Record online: 3 JAN 2008 | DOI: 10.1002/anie.200703998

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      A unique oxidative cyclization of a tricycle bearing a guanidine aminal provides a concise route to the enantioselective synthesis of (+)-phakellin and (+)-monobromophakellin in nine and ten steps, respectively, starting from L-proline (see scheme). This sequence provides a simple annulation strategy applicable to the preparation of more complex members of this family of marine sponge-derived alkaloids including palau'amine.

    16. Structural Aspects of Nucleation Inhibitors for Diastereomeric Resolutions and the Relationship to Dutch Resolution (pages 1287–1290)

      Michel Leeman, Giuseppina Brasile, Edith Gelens, Ton Vries, Bernard Kaptein and Richard Kellogg

      Version of Record online: 10 JAN 2008 | DOI: 10.1002/anie.200704021

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      You say you want a resolution: Nucleation inhibitors for the resolution of diastereomers by selective crystallization have been designed and tested. The resolution of racemic 3-methoxyphenylethylamine was optimized with (S)-mandelic acid as the resolving agent (see scheme). Multifunctional inhibitors are particularly effective.

    17. Immortalizing a Transient Electrophile for DNA Cross-Linking (pages 1291–1293)

      Huan Wang, Manvinder S. Wahi and Steven E. Rokita

      Version of Record online: 3 JAN 2008 | DOI: 10.1002/anie.200704137

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      Who wants to live forever? Compounds that act as strong nucleophiles and good leaving groups repeatedly capture and release a transient quinone methide to extend its effective lifetime under aqueous conditions and promote DNA cross-linking (see scheme). This finding may expand the biological and therapeutic activity of quinone methides.

    18. Use of Sodium Iodide as the Precursor to the Control Agent in Ab Initio Emulsion Polymerization (pages 1294–1297)

      Jeff Tonnar and Patrick Lacroix-Desmazes

      Version of Record online: 2 JAN 2008 | DOI: 10.1002/anie.200704146

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      Iodide does the job: Water-soluble, harmless, cheap, and nonhazardous NaI was used in combination with K2S2O8 instead of I2 itself to produce an uncolored living poly(butyl acrylate) latex of controlled molecular weight by a single-step polymerization process (see scheme for one polymerization pathway). Reactivation of the polymer then yielded a block-copolymer latex. BuA=butyl acrylate.

    19. [2+1] Cycloaddition of Nitrene onto C60 Revisited: Interconversion between an Aziridinofullerene and an Azafulleroid (pages 1298–1300)

      Tsukasa Nakahodo, Mitsunori Okada, Hiroyuki Morita, Toshiaki Yoshimura, Midori O. Ishitsuka, Takahiro Tsuchiya, Yutaka Maeda, Hisashi Fujihara, Takeshi Akasaka, Xingfa Gao and Shigeru Nagase

      Version of Record online: 8 JAN 2008 | DOI: 10.1002/anie.200704410

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      An open and closed case: The reversible interconversion of a [1,2]aziridinofullerene and a [1,6]azafulleroid represents the first such example for a monosubstituted fullerene. While the [1,2]aziridinofullerene rearranges thermally to the [1,6]azafulleroid, the [1,6]azafulleroid rearranges photochemically to the [1,2]aziridinofullerene in high yield (see picture).

    20. Oxidative Cross-Coupling of Arenes Induced by Single-Electron Transfer Leading to Biaryls by Use of Organoiodine(III) Oxidants (pages 1301–1304)

      Toshifumi Dohi, Motoki Ito, Koji Morimoto, Minako Iwata and Yasuyuki Kita

      Version of Record online: 13 DEC 2007 | DOI: 10.1002/anie.200704495

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      Cross-coupling goes green: The direct oxidative cross-coupling reaction of naphthalenes and other electron-rich arenes with mesitylenes has been achieved in high yields using hypervalent iodine(III) reagents. The key for reaction success is the exclusive generation of cation radical intermediates of naphthalenes and the use of mesitylenes as the reactive and less dimerizable nucleophiles. R = alkyl, aryl, halogen, ester, alkoxy, etc.

    21. Iron-Catalyzed Desulfinylative C[BOND]C Cross-Coupling Reactions of Sulfonyl Chlorides with Grignard Reagents (pages 1305–1307)

      Chandra M. Rao Volla and Pierre Vogel

      Version of Record online: 3 JAN 2008 | DOI: 10.1002/anie.200704858

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      A friendly couple: Conditions have been uncovered that allow the desulfinylative C[BOND]C cross-coupling reaction of inexpensive sulfonyl chlorides and Grignard reagents (see scheme, acac=acetylacetonate, NMP=N-methylpyrrolidone). The reactions rely on environmentally friendly iron catalysts and do not require expensive and/or toxic ligands.

    22. An N,N′-Dioxide/In(OTf)3 Catalyst for the Asymmetric Hetero-Diels–Alder Reaction Between Danishefsky's Dienes and Aldehydes: Application in the Total Synthesis of Triketide (pages 1308–1311)

      Zhipeng Yu, Xiaohua Liu, Zhenhua Dong, Mingsheng Xie and Xiaoming Feng

      Version of Record online: 4 JAN 2008 | DOI: 10.1002/anie.200704759

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      In-teresting catalyst: An asymmetric hetero Diels–Alder reaction between Danishefsky's dienes and various aldehydes using an N,N′-dioxide/In(OTf)3 complex affords highly substituted chiral dihydropyranones with up to 99 % ee (see scheme). The catalyst was applied to the synthesis of triketide from propionaldehyde in 72 % yield and with 97 % ee.

    23. Highly Regio-, Diastereo-, and Enantioselective [2+2+2] Cycloaddition of 1,6-Enynes with Electron-Deficient Ketones Catalyzed by a Cationic RhI/H8-binap Complex (pages 1312–1316)

      Ken Tanaka, Yousuke Otake, Hiromi Sagae, Keiichi Noguchi and Masao Hirano

      Version of Record online: 8 JAN 2008 | DOI: 10.1002/anie.200704758

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      Two quaternary carbon centers are created in the title reaction to form fused dihydropyrans (see scheme). The same catalyst promotes the ortho functionalization of aryl ketones with 1,6-enynes with excellent regio- and enantioselectivity. Z=amide, C(CO2Me)2, O; E=CO2Et, Ac; R1=Me, aryl, CO2Me; R2=Me; R3=Me, CO2Et.

    24. Catalytic Enantioselective Reformatsky Reaction with Aldehydes (pages 1317–1319)

      M. Ángeles Fernández-Ibáñez, Beatriz Maciá, Adriaan J. Minnaard and Ben L. Feringa

      Version of Record online: 4 JAN 2008 | DOI: 10.1002/anie.200704841

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      120 years after the discovery of the Reformatsky reaction, the first effective catalytic enantioselective Reformatsky reaction with aldehydes using a binol derivative as a chiral catalyst is presented (see scheme; TMS=trimethylsilyl). The reaction is performed with ethyl iodoacetate and Me2Zn. The presence of air is found to be crucial to reach high conversions and selectivities.

    25. A Hybrid Semiconductor Electrode for Wavelength-Controlled Switching of the Photocurrent Direction (pages 1320–1322)

      Radim Beranek and Horst Kisch

      Version of Record online: 11 JAN 2008 | DOI: 10.1002/anie.200701103

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      A light switch: A nanocrystalline hybrid photoelectrode consisting of nitrogen-modified titanium dioxide (an n-type semiconductor) and copper(I) iodide (a p-type semiconductor) on conducting glass shows wavelength-controlled switching of the photocurrent in the narrow range from 410 to 420 nm (see picture).

    26. Vesicle Formation from Reactive Surfactants (pages 1323–1325)

      Helmut H. Zepik, Peter Walde and Takashi Ishikawa

      Version of Record online: 4 JAN 2008 | DOI: 10.1002/anie.200704022

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      Zwitterionic gemini vesicles: Alkylphosphothioates and N-(2-bromoethyl)-N,N-dimethylalkylammonium surfactants react quantitatively in aqueous buffer to form zwitterionic gemini surfactants. The reaction products transform spontaneously into lipid vesicles that behave similarly to phospholipid vesicles. The zwitterionic gemini vesicles encapsulate water-soluble molecules; when fed with the single-chain precursors, they grow quantitatively.

    27. Synthesis and Crystal Structures of the Ligand-Stabilized Silver Chalcogenide Clusters [Ag154Se77(dppxy)18], [Ag320(StBu)60S130(dppp)12], [Ag352S128(StC5H11)96], and [Ag490S188(StC5H11)114] (pages 1326–1331)

      Christopher E. Anson, Andreas Eichhöfer, Ibrahim Issac, Dieter Fenske, Olaf Fuhr, Paloma Sevillano, Claudia Persau, Dietmar Stalke and Jiatao Zhang

      Version of Record online: 4 JAN 2008 | DOI: 10.1002/anie.200704249

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      The reaction of silver thiolates with Se(SiMe3)2 or S(SiMe3)2 in the presence of bidentate phosphanes leads to the formation of very large cluster molecules with distorted spherical metal–chalcogenide cores with diameters of 2–4 nm. The surfaces of these cores are protected by thiolate and phosphane ligands. Structural analyses show a higher degree of disorder with increasing number of Ag atoms. The compound with the highest silver content (see figure) has an idealized formulation [Ag490S188(StC5H11)114].

    28. Allosteric Activation of HtrA Protease DegP by Stress Signals during Bacterial Protein Quality Control (pages 1332–1334)

      Michael Meltzer, Sonja Hasenbein, Patrick Hauske, Nicolette Kucz, Melisa Merdanovic, Sandra Grau, Alexandra Beil, Dafydd Jones, Tobias Krojer, Tim Clausen, Michael Ehrmann and Markus Kaiser

      Version of Record online: 3 JAN 2008 | DOI: 10.1002/anie.200703273

      Thumbnail image of graphical abstract

      Unleashing the proteolytic activity of DegP: A study with synthetic mimics of cellular stress signals reveals an allosteric (chemical) activation mechanism of the bacterial HtrA protease DegP, leading to a fine-tuned amplification of protein degradation during bacterial protein quality control (see scheme: binding of a peptide sequence (circles) increases activation. The nature of the penultimate residue (red) is shown to be decisive).

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