Angewandte Chemie International Edition

Cover image for Vol. 47 Issue 12

March 7, 2008

Volume 47, Issue 12

Pages 2153–2317

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Obituary
    7. Book Reviews
    8. Highlights
    9. Review
    10. Communications
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    1. Cover Picture: Exploitation of the Dual-emissive Properties of Cyclometalated Iridium(III)–Polypyridine Complexes in the Development of Luminescent Biological Probes (Angew. Chem. Int. Ed. 12/2008) (page 2153)

      Kenneth Kam-Wing Lo, Kenneth Yin Zhang, Siu-Kit Leung and Man-Chung Tang

      Version of Record online: 3 MAR 2008 | DOI: 10.1002/anie.200890047

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      Chameleons change their skin colors in response to temperature and light conditions. In their Communication on page 2213 ff., K. K.-W. Lo et al. describe the discovery of an iridium–polypyridine complex that shows environment-sensitive dual emission. The incorporation of biological substrates into this system results in luminescent probes that exhibit pronounced changes in their emission profiles upon binding to their specific receptors. (Photograph: www.screameleons.com.)

  2. Inside Cover

    1. Top of page
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    4. Graphical Abstract
    5. News
    6. Obituary
    7. Book Reviews
    8. Highlights
    9. Review
    10. Communications
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    1. Inside Cover: Periodic Iron Nanomineralization in Human Serum Transferrin Fibrils (Angew. Chem. Int. Ed. 12/2008) (page 2154)

      Surajit Ghosh, Arindam Mukherjee, Peter J. Sadler and Sandeep Verma

      Version of Record online: 3 MAR 2008 | DOI: 10.1002/anie.200890048

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      Periodic iron mineralization in human serum transferrin fibrils has been observed by microscopy, as described by P. J. Sadler, S. Verma, and co-workers in the Communication on page 2217 ff. The picture shows transferrin as a ribbon structure, typical micrographs of the fibers, and the diffraction pattern of a fiber nanocrystallite (which resembles the iron oxide/hydroxide mineral shown in a space-filling representation). These findings suggest a previously unknown biological role for transferrin.

  3. Graphical Abstract

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    4. Graphical Abstract
    5. News
    6. Obituary
    7. Book Reviews
    8. Highlights
    9. Review
    10. Communications
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  4. News

    1. Top of page
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    4. Graphical Abstract
    5. News
    6. Obituary
    7. Book Reviews
    8. Highlights
    9. Review
    10. Communications
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  5. Obituary

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    1. Helmut Beinert (1913–2007) (page 2172)

      Peter M. H. Kroneck

      Version of Record online: 3 MAR 2008 | DOI: 10.1002/anie.200800392

  6. Book Reviews

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    1. Molecules and Medicine. By E. J. Corey, Barbara Czakó, and László Kürti. (pages 2173–2174)

      Rainer E. Metternich and Christopher S. Burgey

      Version of Record online: 3 MAR 2008 | DOI: 10.1002/anie.200785558

  7. Highlights

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    1. Golden Opportunities in Stereoselective Catalysis (pages 2178–2181)

      Nadine Bongers and Norbert Krause

      Version of Record online: 12 FEB 2008 | DOI: 10.1002/anie.200704729

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      A golden future: The recent discoveries in stereoselective gold catalysis are extremely promising. Transfer of chirality or the generation of new stereogenic centers from prochiral substrates on application of chiral gold catalysts occur with excellent enantioselectivities. New concepts, such as the use of gold catalysts with chiral counterions, help to improve selectivities (see scheme, dppm=bis(diphenylphosphanyl)methane).

    2. Copper-Free Azide–Alkyne Cycloadditions: New Insights and Perspectives (pages 2182–2184)

      Jean-François Lutz

      Version of Record online: 8 FEB 2008 | DOI: 10.1002/anie.200705365

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      Clicking without copper: Copper-mediated azide–alkyne “click” cycloadditions (CuAAC) play a central role in contemporary synthetic chemistry but rely on transition-metal catalysts, which hamper their adoption in some biological applications. Recently, the strain-promoted and fluorine-activated cycloaddition of cyclooctynes and organic azides (see picture) was proposed as an interesting metal-free alternative to CuAAC.

    3. Molecular Magnesium(I) Compounds: From Curiosity to Kudos (pages 2185–2187)

      Matthias Westerhausen

      Version of Record online: 18 FEB 2008 | DOI: 10.1002/anie.200705758

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      Two for one: Molecular magnesium(I) compounds (see structure: Mg light blue, N dark blue, C gray) with astonishing stability are now accessible in good yields. Decomposition reactions are observed at 170 °C and 300 °C, depending on the ligand present.

  8. Review

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    9. Review
    10. Communications
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    1. Electrostatic Charging Due to Separation of Ions at Interfaces: Contact Electrification of Ionic Electrets (pages 2188–2207)

      Logan S. McCarty and George M. Whitesides

      Version of Record online: 12 FEB 2008 | DOI: 10.1002/anie.200701812

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      The ancient Greeks described the phenomenon of contact electrification (“static electricity”), but the detailed mechanism of charge transfer remains unknown. It is now clear that the charge carriers may be ions or electrons (or both), depending on the specific materials involved (see scheme). This Review focuses on ionic electrets—materials that have a net electrostatic charge arising from an imbalance between cationic and anionic charges.

  9. Communications

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Obituary
    7. Book Reviews
    8. Highlights
    9. Review
    10. Communications
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    1. Controlling Colloidal Superparticle Growth Through Solvophobic Interactions (pages 2208–2212)

      Jiaqi Zhuang, Huimeng Wu, Yongan Yang and Y. Charles Cao

      Version of Record online: 31 JAN 2008 | DOI: 10.1002/anie.200705049

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      A supramolecular chemistry approach is used to make supercrystalline spherical colloidal superparticles (SPs, see picture) from nanoparticles. Detailed mechanistic studies show that the formation of the SPs is a two-step process. The major driving force for superparticle formation is the solvophobic interaction between nanoparticle building blocks and the growth solution; fine-tuning the interaction led to a size-controlled synthesis.

    2. Exploitation of the Dual-emissive Properties of Cyclometalated Iridium(III)–Polypyridine Complexes in the Development of Luminescent Biological Probes (pages 2213–2216)

      Kenneth Kam-Wing Lo, Kenneth Yin Zhang, Siu-Kit Leung and Man-Chung Tang

      Version of Record online: 21 FEB 2008 | DOI: 10.1002/anie.200705155

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      A colorful life: A new class of cyclometalated iridium(III)–polypyridine complexes have been discovered to exhibit environment-sensitive dual emission: In polar and nonpolar media the complexes show green and orange-yellow emission, respectively (see picture). This behavior has been utilized in the development of novel luminescent biological probes for avidin, estrogen receptor α, and human serum albumin.

    3. Periodic Iron Nanomineralization in Human Serum Transferrin Fibrils (pages 2217–2221)

      Surajit Ghosh, Arindam Mukherjee, Peter J. Sadler and Sandeep Verma

      Version of Record online: 6 FEB 2008 | DOI: 10.1002/anie.200705723

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      Spotty iron: Surface deposition of holo human transferrin from aqueous solutions gives rise to long protein fibrils with regular periodic nanomineralization along their length of an FeIII oxide/hydroxide closely resembling lepidocrocite (γ-FeO(OH)). Such a new role for this serum protein could have important biological and medical implications.

    4. pH-Responsive Supramolecular Nanovalves Based on Cucurbit[6]uril Pseudorotaxanes (pages 2222–2226)

      Sarah Angelos, Ying-Wei Yang, Kaushik Patel, J. Fraser Stoddart and Jeffrey I. Zink

      Version of Record online: 14 FEB 2008 | DOI: 10.1002/anie.200705211

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      An open and closed case: pH-controllable nanovalves that operate in water have been produced by attaching [2]pseudorotaxanes to the surface of mesoporous silica nanoparticles. The nanovalves are able to contain guest molecules (rhodamine B, red circles) within the nanopores at acidic and neutral pH values but release them on command when the pH value is raised (see picture).

    5. Gold Nanoparticles Coated with a Thermosensitive Hyperbranched Polyelectrolyte: Towards Smart Temperature and pH Nanosensors (pages 2227–2230)

      Yi Shen, Min Kuang, Zhong Shen, Jörg Nieberle, Hongwei Duan and Holger Frey

      Version of Record online: 14 FEB 2008 | DOI: 10.1002/anie.200704572

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      Controlled phase changes: Thermosensitive Au nanoparticles with tunable lower critical solution temperature have been prepared by coating the nanoparticles with a thermo- and pH-responsive hyperbranched polyelectrolyte. The globular, polyfunctional structure of the hyperbranched polymers offer new options to control phase-transition temperatures of the nanoparticles (see aggregation equilibrium in diagram).

    6. Two-Photon Fluorescent Probes for Acidic Vesicles in Live Cells and Tissue (pages 2231–2234)

      Hwan Myung Kim, Myoung Jin An, Jin Hee Hong, Byeong Ha Jeong, Ohyun Kwon, Ju-Yong Hyon, Seok-Cheol Hong, Kyoung J. Lee and Bong Rae Cho

      Version of Record online: 13 FEB 2008 | DOI: 10.1002/anie.200704586

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      Move with the groove: Two-photon fluorescent pH probes and a two-photon lysotracker (AL1) can visualize acidic vesicles in live cells and living tissue for a long period of time without mistargeting and photobleaching problems. Using AL1, vesicles can be tracked in real time (see picture).

    7. DOSY NMR Experiments as a Tool for the Analysis of Constitutional and Motional Dynamic Processes: Implementation for the Driven Evolution of Dynamic Combinatorial Libraries of Helical Strands (pages 2235–2239)

      Nicolas Giuseppone, Jean-Louis Schmitt, Lionel Allouche and Jean-Marie Lehn

      Version of Record online: 14 FEB 2008 | DOI: 10.1002/anie.200703168

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      Diffusion ordered spectroscopy (DOSY) NMR experiments have been used to characterize a dynamic combinatorial library of helical strands and grid-type metallosupramolecular architectures. The technique allows the deconvolution of very similar chemical structures differing only by their hydrodynamic radius. Moreover, the occurrence of springlike, extension–contraction conformational motions in helical strands can be revealed as a function of the temperature.

    8. Reversible Switching between Macrocyclic and Polymeric States by Morphological Control in a Constitutional Dynamic System (pages 2240–2243)

      Sébastien Ulrich and Jean-Marie Lehn

      Version of Record online: 14 FEB 2008 | DOI: 10.1002/anie.200704946

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      Exchanging loose ends: The combination of a morphologically controlled core and reversible covalent linkages allows the reversible switching of a dynamic system between two states, a macrocyclic and a polymeric one (see picture). The process demonstrates that a constitutional dynamic system may undergo a constitutional change on modification of morphological information.

      Corrected by:

      Corrigendum: Reversible Switching between Macrocyclic and Polymeric States by Morphological Control in a Constitutional Dynamic System

      Vol. 47, Issue 24, 4462, Version of Record online: 27 MAY 2008

    9. From Disulfide- to Thioether-Linked Glycoproteins (pages 2244–2247)

      Gonçalo J. L. Bernardes, Elizabeth J. Grayson, Sam Thompson, Justin M. Chalker, James C. Errey, Farid El Oualid, Timothy D. W. Claridge and Benjamin G. Davis

      Version of Record online: 14 FEB 2008 | DOI: 10.1002/anie.200704381

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      Strengthening the bond: The introduction of a thiol tag in combination with chemoselective ligation to form a disulfide-linked bioconjugate is a selective and useful method for site-selective protein glycosylation. The phosphine-mediated desulfurization of such glycoconjugates to their reductant-resistant thioether-linked counterparts completes a convergent, site-selective synthesis of thioether-linked glycoproteins (see scheme).

    10. Ring Selectivity: Successive Ring Expansion of Two Benzocyclobutenes for Divergent Access to Angular and Linear Benzanthraquinones (pages 2248–2252)

      Takeaki Suzuki, Toshiyuki Hamura and Keisuke Suzuki

      Version of Record online: 14 FEB 2008 | DOI: 10.1002/anie.200705630

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      Which ring shall it be? The successive thermal ring expansion of two benzocyclobutenes connected by an ethene bridge enables the expeditious synthesis of benzanthraquinones (see scheme). The key to the success of this approach is the selective electrocyclic ring opening of one of the benzocyclobutene moieties in the initial stage of the process.

    11. Visualizing Metabolically Labeled Glycoconjugates of Living Cells by Copper-Free and Fast Huisgen Cycloadditions (pages 2253–2255)

      Xinghai Ning, Jun Guo, Margreet A. Wolfert and Geert-Jan Boons

      Version of Record online: 14 FEB 2008 | DOI: 10.1002/anie.200705456

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      CuI-free click: 4-Dibenzocyclooctynol reacts, in the absence of a CuI catalyst, exceptionally fast with azido-containing saccharides and amino acids to give stable triazoles. A biotin-modified derivative is ideally suited for visualizing and tracking glycoconjugates of living cells that are metabolically labeled with azido-containing monosaccharides (see image).

    12. Intercluster Compounds Consisting of Gold Clusters and Fullerides: [Au7(PPh3)7]C60⋅THF and [Au8(PPh3)8](C60)2 (pages 2256–2259)

      Martin Schulz-Dobrick and Martin Jansen

      Version of Record online: 8 FEB 2008 | DOI: 10.1002/anie.200705373

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      Balls and bunches: [Au7(PPh3)7]C60⋅THF (see picture) and [Au8(PPh3)8](C60)2 are the first intercluster compounds consisting of gold clusters and fullerides. The interplay between long-range Coulomb interactions and short-range C[BOND]H–π and π–π interactions is responsible for the formation of well-crystalline compounds with a conspicuous segregation of the cations' and anions' partial structures.

    13. Chemical Communication between Metal-Complex-Based Monolayers (pages 2260–2262)

      Tarkeshwar Gupta and Milko E. van der Boom

      Version of Record online: 13 FEB 2008 | DOI: 10.1002/anie.200705841

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      Look who's talking: Redox-induced chemical communication between surface-confined osmium(II) and ruthenium(III) polypyridyl complexes in organic solvents has been demonstrated. Fe2+ was used as electron carrier (see picture), and the output signal of the monolayer reporter system was read optically with a conventional UV/Vis spectrophotometer in the transmission mode. Electron transfer takes place at surface–solution interfaces.

    14. Gold(I)-Catalyzed Cycloisomerization of 3-Methoxy-1,6-enynes Featuring Tandem Cyclization and [3,3]-Sigmatropic Rearrangement (pages 2263–2266)

      Hyo J. Bae, Baburaj Baskar, Sang E. An, Jae Y. Cheong, Daniel T. Thangadurai, In-Chul Hwang and Young H. Rhee

      Version of Record online: 11 FEB 2008 | DOI: 10.1002/anie.200705117

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      Golden reactivity: A new gold(I)-catalyzed cycloisomerization of 3-methoxy-1,6-enynes was discovered. Structurally simple 3-methoxy-1,6-enynes engage in a tandem cyclization/[3,3]-sigmatropic rearrangement to deliver a variety of 1-methoxy-1,4-cycloheptadienes (see scheme). Notably, the reaction can be performed under very mild conditions and the synthetic utility of this reaction was demonstrated by facile conversion of the product into various cyclohept-4-en-1-ones.

    15. Diaminocarbene[3]ferrocenophanes and Their Transition-Metal Complexes (pages 2267–2270)

      Dimitri M. Khramov, Evelyn L. Rosen, Vincent M. Lynch and Christopher W. Bielawski

      Version of Record online: 7 FEB 2008 | DOI: 10.1002/anie.200704978

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      Jones'n for electrons: Various Rh complexes (see general structure) were formed with diaminocarbenes that contain 1,1′-disubstituted ferrocenes in their backbones. Electronic communication between the Fe centers in the redox-active carbenes and the coordinated transition metals was observed. For example, the oxidation potential of the Fe center in a bimetallic complex was found to depend on the electron density of the ligated Rh atom.

    16. Palladium–Oxygen and Palladium–Arene Interactions in Complexes Derived from Biaryl Aminocarbenes: Comparison with Biaryl Phosphanes (pages 2271–2274)

      Joan Vignolle, Heinz Gornitzka, Bruno Donnadieu, Didier Bourissou and Guy Bertrand

      Version of Record online: 13 FEB 2008 | DOI: 10.1002/anie.200704927

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      Similar yet very different: Biaryl aminocarbenes were prepared, characterized spectroscopically, and coordinated to an allylpalladium fragment (see scheme). In the resulting Pd complexes of these bidentate hemilabile ligands, secondary Pd–O and Pd–arene interactions were observed that differ markedly from those encountered in complexes of the related biaryl phosphanes.

    17. Self-Sufficient Baeyer–Villiger Monooxygenases: Effective Coenzyme Regeneration for Biooxygenation by Fusion Engineering (pages 2275–2278)

      Daniel E. Torres Pazmiño, Radka Snajdrova, Bert-Jan Baas, Michael Ghobrial, Marko D. Mihovilovic and Marco W. Fraaije

      Version of Record online: 25 JAN 2008 | DOI: 10.1002/anie.200704630

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      Two-in-one biocatalysts were engineered by the covalent fusion of NADPH-dependent Baeyer–Villiger monooxygenases to a phosphite dehydrogenase for coenzyme regeneration (see scheme). Not only the purified fusion proteins, but also whole cells and crude cell extracts containing the enzyme conjugates, could be used to catalyze biotransformations with high efficiency. NADP+=nicotinamide adenine dinucleotide phosphate.

    18. Nickel-Catalyzed Reductive Cyclization of Unactivated 1,6-Enynes in the Presence of Organozinc Reagents (pages 2279–2282)

      Mao Chen, Yue Weng, Mian Guo, Hua Zhang and Aiwen Lei

      Version of Record online: 8 FEB 2008 | DOI: 10.1002/anie.200704452

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      Pyrrolidine and tetrahydrofuran derivatives were synthesized in a highly stereoselective manner through the Ni-catalyzed reduction of the title compounds under mild conditions (see scheme). The product of cyclization is initially associated with both a Ni and a Zn species, the removal of which by elimination and hydrolysis corresponds to the formal incorporation of dihydrogen. acac=acetylacetonate; R=alkyl, aryl; X=N, O.

    19. Product Selection through Photon Flux: Laser-Specific Lactone Synthesis (pages 2283–2286)

      Claudio Roscini, David M. E. Davies, Malcolm Berry, Andrew J. Orr-Ewing and Kevin I. Booker-Milburn

      Version of Record online: 18 FEB 2008 | DOI: 10.1002/anie.200704816

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      Lasers flux their muscles: The Norrish type I and type II reactions of 1,3-indandiones can be controlled by judicious choice of light source. Selectivity depends on photon flux, not wavelength. Laser irradiation lead to lactones (type I); conventional lamp irradiation gives diketones by fragmentation (type II, see scheme).

    20. Iron-Nanoparticle-Catalyzed Hydrolytic Dehydrogenation of Ammonia Borane for Chemical Hydrogen Storage (pages 2287–2289)

      Jun-Min Yan, Xin-Bo Zhang, Song Han, Hiroshi Shioyama and Qiang Xu

      Version of Record online: 11 FEB 2008 | DOI: 10.1002/anie.200704943

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      Attractive hydrogen production? The amorphous Fe nanoparticles prepared following a simple but very efficient method possess high catalytic activity (see picture) for the generation of hydrogen from an aqueous solution of ammonia borane, even in air, and can readily be recycled with no obvious loss of catalytic activity.

    21. A Highly Active Chiral Indium Catalyst for Living Lactide Polymerization (pages 2290–2293)

      Amy F. Douglas, Brian O. Patrick and Parisa Mehrkhodavandi

      Version of Record online: 13 FEB 2008 | DOI: 10.1002/anie.200705033

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      It loves LA! A unique chiral dinuclear indium complex 1 (see structure; In gray, Cl green, O red, N blue, C black) has been developed as a catalyst for the highly active, living ring-opening polymerization of lactide (LA). The catalyst retains the same reaction rate during two consecutive additions of lactide, and there is significant site control of polymer tacticity.

    22. Highly Stereoselective Synthesis of Substituted γ-Lactams from Acylsilanes (pages 2294–2297)

      Robert B. Lettan II, Chase C. Woodward and Karl A. Scheidt

      Version of Record online: 12 FEB 2008 | DOI: 10.1002/anie.200705229

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      It takes three: The stereoselective synthesis of highly substituted γ-lactams from amide enolates, acylsilanes, and imines is reported. This multicomponent reaction accesses γ-amino-β-hydroxy amides in a single flask with good yields and excellent levels of diastereoselectivity (see scheme). Exposure of the linear products to microwave irradiation and acidic conditions promotes a cyclization to form the corresponding γ-lactams in excellent yields.

    23. Enantio- and Diastereoselective Hydrogenation of Farnesol and O-Protected Derivatives: Stereocontrol by Changing the C[DOUBLE BOND]C Bond Configuration (pages 2298–2300)

      Aie Wang, Bettina Wüstenberg and Andreas Pfaltz

      Version of Record online: 12 FEB 2008 | DOI: 10.1002/anie.200705521

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      Four isomers–one catalyst: The four stereoisomers of hexahydrofarnesol can be prepared with high enantio- and diastereoselectivity by using the same chiral iridium catalyst 1 with different cis/trans isomers of farnesol (see scheme; BArF=tetrakis[bis-3,5-(trifluoromethyl)phenyl]borate). Both the internal trialkyl-substituted C[DOUBLE BOND]C bond and the allylic alcohol unit are hydrogenated with high facial selectivity.

    24. The η61-Coordination of Beryllium Atoms in the Graphite Analogue BeB2C2 (pages 2301–2303)

      Kathrin Hofmann, Xavier Rocquefelte, Jean-François Halet, Carsten Bähtz and Barbara Albert

      Version of Record online: 14 FEB 2008 | DOI: 10.1002/anie.200705023

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      Nonsymmetrical coordination favored: The structure of BeB2C2 (see picture; Be white, B dark gray, C light gray) has been solved using near-edge fine-structure analysis of electron energy loss spectra and high-resolution powder diffractometry. It exhibits the unusual features of graphite-analogous B/C layers and a nonsymmetrical coordination of the beryllium atoms. The latter reveals a striking parallelism of the molecular and solid-state chemistries of Be compounds.

    25. Zinc-Promoted Hydrohydrazination of Terminal Alkynes: An Efficient Domino Synthesis of Indoles (pages 2304–2307)

      Karolin Alex, Annegret Tillack, Nicolle Schwarz and Matthias Beller

      Version of Record online: 8 FEB 2008 | DOI: 10.1002/anie.200703823

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      Indole click chemistry: The quest for better catalysts for the intermolecular hydrohydrazination to indoles leads to zinc salts. A simple one-pot synthesis forms indoles from arylhydrazines and terminal alkynes. The pharmacologically relevant indole building blocks are selectively formed in the presence of zinc triflate (Zn(OTf)2) or ZnCl2 (see scheme).

    26. Stereochemical Determination of Thuggacins A–C, Highly Active Antibiotics from the Myxobacterium Sorangium cellulosum (pages 2308–2311)

      Martin Bock, Kathrin Buntin, Rolf Müller and Andreas Kirschning

      Version of Record online: 14 FEB 2008 | DOI: 10.1002/anie.200704897

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      Chemistry and biology meet in the structure elucidation of the antibiotics thuggacins A–C. The absolute configuration of all stereogenic centers in the thuggacins was confirmed through a combination of chemical derivatization, NMR analysis, molecular modeling, and bioinformatic analysis of the thuggacin biosynthetic genes.

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    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Obituary
    7. Book Reviews
    8. Highlights
    9. Review
    10. Communications
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