Angewandte Chemie International Edition

Cover image for Vol. 45 Issue 37

September 18, 2006

Volume 45, Issue 37

Pages 6063–6229

  1. Cover Picture

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    1. Cover Picture: Making the True “CP” Ligand (Angew. Chem. Int. Ed. 37/2006) (page 6063)

      Joseph G. Cordaro, Daniel Stein, Heinz Rüegger and Hansjörg Grützmacher

      Article first published online: 11 SEP 2006 | DOI: 10.1002/anie.200690125

      The quest for cyaphide, the phosphorus equivalent of cyanide, has been a challenge for many years. In their Communication on page 6159 ff., H. Grützmacher and co-workers describe their approach to prepare the first stable terminal cyaphide complex [RuH(CP)(dppe)2] (dppe=bis(1,2-diphenylphosphinoethane)). In an initial silyl-protected complex, the Ru center was P-coordinated by the C[TRIPLE BOND]P ligand. Removal of the silyl group yielded the C-coordinated Ru complex, whose structure is shown on the cover picture.

  2. Graphical Abstract

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  3. News

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  4. Book Reviews

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  5. Highlight

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    1. From Olefin to Alkane Metathesis: A Historical Point of View (pages 6082–6085)

      Jean-Marie Basset, Christophe Copéret, Daravong Soulivong, Mostafa Taoufik and Jean Thivolle-Cazat

      Article first published online: 29 AUG 2006 | DOI: 10.1002/anie.200602155

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      Is two better than one? The recent discovery of a homogeneous catalytic system for alkane metathesis is analyzed and compared to other existing systems. The new catalytic system is a combination of two catalysts that carry out dehydrogenation/hydrogenation and olefin metathesis (see scheme).

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    1. Macrocyclization by Ring-Closing Metathesis in the Total Synthesis of Natural Products: Reaction Conditions and Limitations (pages 6086–6101)

      Ana Gradillas and Javier Pérez-Castells

      Article first published online: 21 AUG 2006 | DOI: 10.1002/anie.200600641

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      Closing the circle: The formation of macrocycles by ring-closing metathesis (RCM) has for a long time been a key step in the synthesis of natural products that contain large rings. Which reaction conditions are preferable for a macro-RCM? An overview of the current research is given to help when planning future key macrocyclization steps in the synthesis of natural macrocycles.

      Corrected by:

      Corrigendum: Macrocyclization by Ring-Closing Metathesis in the Total Synthesis of Natural Products: Reaction Conditions and Limitations

      Vol. 45, Issue 48, 8086, Article first published online: 4 DEC 2006

  7. Review

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    1. Encoded Microcarriers For High-Throughput Multiplexed Detection (pages 6104–6117)

      Robert Wilson, Andrew R. Cossins and David G. Spiller

      Article first published online: 29 AUG 2006 | DOI: 10.1002/anie.200600288

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      Faster, smaller, more sensitive: Since the decoding of the human genome a defining trait has been the quest to obtain more and more molecular information from smaller and smaller samples. Latex microspheres encoded with fluorescent dyes allow dozens of molecules to be detected in the same sample at the same time, but the race is now on to develop new types of encoded particle that can extract even more information.

  8. Communications

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    1. Cationic Terminal Borylene Complexes: Structure/Bonding Analysis and [4+1] Cycloaddition Reactivity of a BN Vinylidene Analogue (pages 6118–6122)

      Simon Aldridge, Cameron Jones, Timo Gans-Eichler, Andreas Stasch, Deborah L. Kays (née Coombs), Natalie D. Coombs and David J. Willock

      Article first published online: 25 JUL 2006 | DOI: 10.1002/anie.200602162

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      Charge changes everything: The cationic terminal aminoborylene complex [CpFe(CO)2(BNCy2)]+[BArF4] (1, Cy= cyclohexyl, ArF=3,5-(CF3)2C6H3; Fe orange, B green, N blue, O red, C gray) was structurally characterized. DFT studies (see HOMO−2) indicate delocalized π bonding along the linear Fe-B-N framework and significant Fe[BOND]B and B[BOND]N multiple-bond character.

    2. Helicity Inversion in Lanthanide(III) Complexes with Chiral Nonaaza Macrocyclic Ligands (pages 6122–6126)

      Janusz Gregoliński and Jerzy Lisowski

      Article first published online: 21 AUG 2006 | DOI: 10.1002/anie.200602464

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      Giving lanthanides a new twist: The chiral nonaaza macrocycle L wraps tightly around lanthanide(III) ions in a helical fashion (see picture). The all-R enantiomer of the macrocycle, LRRRRRR, forms kinetically controlled complexation products of M helicity (100 % de), which undergo inversion to the P diastereomer (90 % de). Both products have been isolated in enantiopure form and structurally characterized.

      Corrected by:

      Corrigendum: Helicity Inversion in Lanthanide(III) Complexes with Chiral Nonaaza Macrocyclic Ligands

      Vol. 47, Issue 52, 10013, Article first published online: 12 DEC 2008

    3. A Multifunctional Metal–Organic Open Framework with a bcu Topology Constructed from Undecanuclear Clusters (pages 6126–6130)

      Qian-Rong Fang, Guang-Shan Zhu, Zhao Jin, Ming Xue, Xiao Wei, De-Jun Wang and Shi-Lun Qiu

      Article first published online: 27 JUL 2006 | DOI: 10.1002/anie.200601668

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      Flexible ligands afford large pores: A novel metal–organic framework constructed from cadmium carboxylate cluster secondary building units and formic acid bridging molecules is reported (see picture). This highly porous material displays rare body-centered cubic topology, as well as good sorption characteristics and optoelectronic properties.

    4. Highly Diastereo- and Enantioselective Mukaiyama Aldol Reactions Catalyzed by Hydrogen Bonding (pages 6130–6133)

      Jeff D. McGilvra, Aditya K. Unni, Kriti Modi and Viresh H. Rawal

      Article first published online: 14 AUG 2006 | DOI: 10.1002/anie.200601638

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      Enzyme lite: Like a minimalist enzyme, a simple chiral alcohol of the taddol family, 1, catalyzes Mukaiyama aldol reactions between silyl enolates of amides and aldehydes to afford products with high diastereo- and enantioselectivities (see scheme; TBS=tert-butyldimethylsilyl).

    5. A Population of Thermostable Reverse Transcriptases Evolved from Thermus aquaticus DNA Polymerase I by Phage Display (pages 6133–6137)

      Sophie Vichier-Guerre, Stéphane Ferris, Nicolas Auberger, Karim Mahiddine and Jean-Luc Jestin

      Article first published online: 12 JUL 2006 | DOI: 10.1002/anie.200601217

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      Running in reverse: A set of enzymes selected according to their RNA-dependent DNA polymerase activity from a library of more than 107 mutant enzymes has been characterized. The product was specifically bound to catalytically active proteins displayed on filamentous bacteriophage. The selected variants have a catalytic efficiency for reverse transcription that is two orders of magnitude higher.

      Corrected by:

      Corrigendum: A Population of Thermostable Reverse Transcriptases Evolved from Thermus aquaticus DNA Polymerase I by Phage Display

      Vol. 49, Issue 7, 1184, Article first published online: 1 FEB 2010

    6. Evidence That a Miniature CuI Metalloprotein Undergoes Collisional Electron Transfer in the Inverted Marcus Region (pages 6137–6140)

      Jing Hong, Olesya A. Kharenko, Jiufeng Fan, Fei Xie, Amy K. Petros, Brian R. Gibney and Michael Y. Ogawa

      Article first published online: 22 AUG 2006 | DOI: 10.1002/anie.200601517

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      It takes two to transfer: A synthetic CuI metalloprotein undergoes bimolecular photoinduced electron transfer in the inverted Marcus regime. The buried CuI4S4(N/O)4 cofactor (purple) has a high reorganization energy and experiences weak electronic coupling to electron acceptors (Q) in the bulk solvent. This lowers kET below the diffusion limit and allows observation of inverted Marcus behavior.

    7. Bimolecular Control over Polypropene Stereochemical Microstructure in a Well-Defined Two-State System and a New Fundamental Form: Stereogradient Polypropene (pages 6140–6144)

      Matthew B. Harney, Yonghui Zhang and Lawrence R. Sita

      Article first published online: 21 AUG 2006 | DOI: 10.1002/anie.200601616

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      A new slant on polypropene: By taking advantage of the living nature of propene polymerization in a well-defined two-state system, an unlimited variety of polypropene microstructures, including a new stereogradient structure, can be prepared with stereochemical microstructural homogeneity.

    8. Four-Color, Enzyme-Free Interrogation of DNA Sequences with Chemically Activated, 3′-Fluorophore-Labeled Nucleotides (pages 6144–6148)

      Niels Griesang, Kerstin Gießler, Tanja Lommel and Clemens Richert

      Article first published online: 22 AUG 2006 | DOI: 10.1002/anie.200600804

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      Color reveals base: The enzymatic template-directed elongation of primers with fluorophore-labeled nucleoside triphosphates is the most frequently used reaction for determining DNA sequences. Primer extension followed by optical read out can now be achieved without enzymes.

    9. 2D NMR Spectroscopic Evidence for Unprecedented Interactions of cis-[Rh2(dap)(μ-O2CCH3)21-O2CCH3)(CH3OH)](O2CCH3) with a DNA Oligonucleotide: Combination of Intercalative and Coordinative Binding (pages 6148–6151)

      Mijeong Kang, Abdellatif Chouai, Helen T. Chifotides and Kim R. Dunbar

      Article first published online: 22 AUG 2006 | DOI: 10.1002/anie.200600938

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      Slip it in: The dual capability of intercalation and coordination binding of dirhodium complexes was observed in the reaction of the title complex with d(CTCTCAACTTCC). A major adduct with the 1,12-diazaperylene (dap) group intercalated between the A6 and A7 residues was produced. Additionally, the Rh atom that is not bound to the dap group forms a coordinative bond to the N7 site of A6.

    10. Phosphole-Modified Poly(thiophene)s: Unique Postfunctionalizable Conjugated Polymers That Sense Elemental Chalcogenides (pages 6152–6155)

      Manuel Sebastian, Muriel Hissler, Claire Fave, Joëlle Rault-Berthelot, Christophe Odin and Régis Réau

      Article first published online: 14 AUG 2006 | DOI: 10.1002/anie.200601844

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      Bulk response: Following the development of conjugated polymers that sense ions or neutral molecules, the first π-conjugated polymer which is capable of detecting elemental chalcogens is presented. Individual reactions at the phosphole moieties (see picture) result in macroscopic responses of the bulk polymer.

    11. Anion-Templated Syntheses of Pseudopeptidic Macrocycles (pages 6155–6159)

      Miriam Bru, Ignacio Alfonso, M. Isabel Burguete and Santiago V. Luis

      Article first published online: 14 AUG 2006 | DOI: 10.1002/anie.200602206

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      A very welcome guest: The terephthalate anion efficiently templates the selective assembly of a tetraimino dianion host–guest complex, which can be reduced to the final [2+2] pseudopeptidic macrocycle (see scheme; O red, blue N).

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      Making the True “CP” Ligand (pages 6159–6162)

      Joseph G. Cordaro, Daniel Stein, Heinz Rüegger and Hansjörg Grützmacher

      Article first published online: 28 AUG 2006 | DOI: 10.1002/anie.200602499

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      Cyaphide attained: A high-yielding synthesis for the first stable terminal cyaphide complex [RuH(CP)(dppe)2] (dppe=bis(1,2-diphenylphosphinoethane); see structure: P orange, Ru silver, C gray, H white) was developed from the silyl-substituted phosphaalkyne complex [RuH(dppe)2(Ph3SiC[TRIPLE BOND]P)]OTf (OTf=CF3SO3) and sodium phenoxide.

    13. Endowing Aspecific, Unbridged-Metallocene Propylene-Polymerization Catalysts with Isospecificity: The Unprecedented Role of MAO (pages 6163–6166)

      Seong Kyun Kim, Hwa Kyu Kim, Min Hyung Lee, Seung Woong Yoon and Youngkyu Do

      Article first published online: 22 AUG 2006 | DOI: 10.1002/anie.200600666

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      Unbridged yet isospecific metallocene polypropylene catalytic systems can be generated in situ during the MAO-assisted activation step (see picture; MAO=methyl aluminum oxane), as demonstrated with a dimethylaminophenyl-substituted zirconocene that has a racemic, C2-symmetric structure in the solid state and produces highly isotactic polypropylene.

    14. Onset of Crystalline Order in 1-Nonanethiol Monolayers Deposited from Solution (pages 6166–6169)

      María José Capitán, Jesús Álvarez, Juan José Calvente and Rafael Andreu

      Article first published online: 14 AUG 2006 | DOI: 10.1002/anie.200600926

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      Reversible switching between order and disorder in a 1-nonanethiol selfassembled monolayer (SAM) is easily accomplished by alternately exposing the monolayer to liquid ethanol then to a helium stream (see picture). Upon removing the liquid phase, the development of crystalline order in the monolayer takes place over a time scale of hours, which implies the sequential crystallization of individual thiol domains.

    15. Luminescent Dinuclear Platinum(II) Terpyridine Complexes with a Flexible Bridge and “Sticky Ends” (pages 6169–6173)

      Vivian Wing-Wah Yam, Kenneth Hoi-Yiu Chan, Keith Man-Chung Wong and Ben Wai-Kin Chu

      Article first published online: 17 AUG 2006 | DOI: 10.1002/anie.200600962

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      Sticking together: Dinuclear platinum(II) terpyridyl complexes display a high tendency towards intramolecular self-association, in which the two Pt terpy units “stick together”. The driving force is provided by metal–metal and π–π interactions which can be controlled by temperature modulation.

    16. Thermoresponsive Micelles from Oligopeptide-Grafted Cyclotriphosphazenes (pages 6173–6176)

      Yong Joo Jun, Udaya S. Toti, Hye Young Kim, Ji Young Yu, Byeongmoon Jeong, Moo Jin Jun and Youn Soo Sohn

      Article first published online: 14 AUG 2006 | DOI: 10.1002/anie.200601108

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      Hard graft: Amphiphilic cyclic phosphazene trimers grafted with hydrophobic oligopeptide (red) and hydrophilic methoxypolyethylene glycol (blue) show a variety of thermoresponsive properties including lower critical solution temperatures near body temperature. They form strong micelles in aqueous solution at an appropriate hydrophobic-to-hydrophilic balance.

    17. Direct Assembly of Nucleoside Precursors from Two- and Three-Carbon Units (pages 6176–6179)

      Carole Anastasi, Michael A. Crowe, Matthew W. Powner and John D. Sutherland

      Article first published online: 17 AUG 2006 | DOI: 10.1002/anie.200601267

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      Sweetness and life: Pentose aminooxazolines—intermediates in potentially prebiotic nucleoside synthesis—can be produced in water from a reaction that bypasses the corresponding sugar. 2-Aminooxazole, a condensation product of glycolaldehyde and cyanamide, reacts with glyceraldehyde under mild conditions in a remarkable process that is essentially quantitative, and is highly stereoselective for ribose and arabinose aminooxazolines.

    18. Family 4 Glycosidases Carry Out Efficient Hydrolysis of Thioglycosides by an α,β-Elimination Mechanism (pages 6179–6182)

      Vivian L. Y. Yip and Stephen G. Withers

      Article first published online: 17 AUG 2006 | DOI: 10.1002/anie.200601421

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      Thioglycosides are widely used as competitive inhibitors of glycosidases. The first glycosidase capable of hydrolyzing unactivated thioglycosides—BglT, a 6-phospho-β-glucosidase from glucosidase family 4—has been found. The efficient cleavage of the thioglycosidic linkage is a consequence of the α,β-elimination mechanism used by GH4 enzymes, in contrast to the nucleophilic displacement mechanisms of “classical” glycosidases.

    19. Radical Alkylation of Bis(silyloxy)enamine Derivatives of Organic Nitro Compounds (pages 6182–6186)

      Jin Young Lee, Young-Taek Hong and Sunggak Kim

      Article first published online: 14 AUG 2006 | DOI: 10.1002/anie.200601461

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      Alkylation β to a nitro group by radical chemistry is made possible by initial conversion of the organic nitro compound into a bis(silyloxy)enamine (see scheme; TBSOTf=tert-butyldimethylsilyl trifluoromethanesulfonate). An advantage of the method is the simultaneous conversion of the nitro group into a synthetically useful oxime ether group.

    20. Synthesis and Study of Janus Bis(carbene)s and Their Transition-Metal Complexes (pages 6186–6189)

      Dimitri M. Khramov, Andrew J. Boydston and Christopher W. Bielawski

      Article first published online: 14 AUG 2006 | DOI: 10.1002/anie.200601583

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      Deuces wild: From catalysis through materials science to biology, N-heterocyclic carbenes (NHCs) can truly be regarded as a wild card of ligands. A new series of “two-faced” (Janus-type) ligands composed of two linearly opposed NHCs fused to an arene linker has been synthesized and can be used to prepare discrete bimetallic complexes.

    21. White Metallopolyynes for Optical Limiting/Transparency Trade-off Optimization (pages 6189–6193)

      Gui-Jiang Zhou, Wai-Yeung Wong, Zhenyang Lin and Cheng Ye

      Article first published online: 17 AUG 2006 | DOI: 10.1002/anie.200601651

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      High-transparency optical limiters: A series of solution-processable white metallopolyynes are shown to be excellent optical power limiters (see picture) with optimized optical transparency/nonlinearity trade-off. They exhibit an optical-limiting performance superior to those of the common reverse saturable absorption dyes, such as C60 and metal phthalocyanine complexes.

    22. Configurationally Stable Molecular Propellers: First Resolution of Residual Enantiomers (pages 6193–6196)

      Tiziana Benincori, Giuseppe Celentano, Tullio Pilati, Alessandro Ponti, Simona Rizzo and Francesco Sannicolò

      Article first published online: 23 AUG 2006 | DOI: 10.1002/anie.200601869

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      Fixing the propeller: There is general consensus that phosphine oxides and phosphines carrying three identical aryl groups are operationally achiral compounds. Herein it is shown that suitably tailored triarylphosphine oxides give rise to configurationally stable residual enantiomers, which were isolated in an enantiopure state.

      Corrected by:

      Corrigendum: Configurationally Stable Molecular Propellers: First Resolution of Residual Enantiomers

      Vol. 45, Issue 47, 7870, Article first published online: 27 NOV 2006

    23. Total Synthesis of Pseudolaric Acid A (pages 6197–6201)

      Zhe Geng, Bin Chen and Pauline Chiu

      Article first published online: 14 AUG 2006 | DOI: 10.1002/anie.200602056

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      The antiangiogenic and cytotoxic natural product pseudolaric acid A ((−)-1) has been obtained by a 26-step synthetic route. This enantioselective synthesis employed an intramolecular carbene cyclization cycloaddition cascade reaction as the key step to construct the carbocyclic framework. PMB=para-methoxybenzyl.

    24. Alkane Metathesis Catalyzed by a Well-Defined Silica-Supported Mo Imido Alkylidene Complex: [([TRIPLE BOND]SiO)Mo([DOUBLE BOND]NAr)([DOUBLE BOND]CHtBu)(CH2tBu)] (pages 6201–6203)

      Frédéric Blanc, Christophe Copéret, Jean Thivolle-Cazat and Jean-Marie Basset

      Article first published online: 17 AUG 2006 | DOI: 10.1002/anie.200602171

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      A two-functions-in-one catalyst precursor allows an olefin metathesis catalyst to be turned into an alkane metathesis catalyst. A silica-supported alkyl alkylidene molybdenum complex containing an ancillary imido ligand is a highly active olefin metathesis catalyst and also acts as a catalyst precursor for alkane metathesis. This system involves a single metal with dual properties and shows that ancillary ligands are compatible with alkane metathesis reactions.

    25. Iridium-Catalyzed Enantioselective Synthesis of Allylic Alcohols: Silanolates as Hydroxide Equivalents (pages 6204–6207)

      Isabelle Lyothier, Christian Defieber and Erick M. Carreira

      Article first published online: 17 AUG 2006 | DOI: 10.1002/anie.200602408

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      Masked hydroxide: A highly regio- and enantioselective Ir-catalyzed allylic etherification of acyclic, achiral allylic carbonates can be achieved by using potassium silanolates as nucleophiles. The use of these hydroxide equivalents allows access to valuable chiral allylic alcohols.

    26. A General Approach to the Covalent Immobilization of Single Polymers (pages 6207–6210)

      Li Liu and Mingdi Yan

      Article first published online: 14 AUG 2006 | DOI: 10.1002/anie.200602097

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      Stuck fast: The covalent immobilization of polymeric single molecules is achieved by the photochemically induced C[BOND]H/N[BOND]H insertion reaction of perfluorophenylazides (see picture). When the concentration of the surface azido groups is decreased, isolated polymeric single molecules are observed. This technique is especially suited for materials that do not possess functional groups and are difficult to be immobilized by other means.

    27. Quantum Chemical Calculations Predict the Diphenyl Diuranium Compound [PhUUPh] To Have a Stable 1Ag Ground State (pages 6210–6213)

      Giovanni La Macchia, Marcin Brynda and Laura Gagliardi

      Article first published online: 14 AUG 2006 | DOI: 10.1002/anie.200602280

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      Nice to see U2! The [PhUUPh] molecule (see picture; U pink, C gray, H white) has been studied by multiconfigurational quantum chemical methods. It was found that a quintuple bond is formed between the two uranium atoms with a U[BOND]U bond length of 2.29 Å. The phenyl ligand was used to mimic a bulky terphenyl ligand, which could be a promising candidate for the stabilization of multiply bonded uranium compounds.

    28. A Supramolecular Photocatalyst for the Production of Hydrogen and the Selective Hydrogenation of Tolane (pages 6215–6218)

      Sven Rau, Bernhard Schäfer, Dieter Gleich, Ernst Anders, Manfred Rudolph, Manfred Friedrich, Helmar Görls, William Henry and Johannes G. Vos

      Article first published online: 17 AUG 2006 | DOI: 10.1002/anie.200600543

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      Light-driven metallo-organic catalysis: Intramolecular photoelectron transfer in the heterodinuclear complex 1 facilitates the photocatalytic production of hydrogen and the selective hydrogenation of tolane to give cis-stilbene. All three well-coordinated parts of the supramolecular system are essential: the (tbbpy)2Ru fragment as a photoactive unit, the redox-active bridging ligand as an electron relay and storage site, and the palladium as a catalytically active center.

    29. Efficient Oxidative Cyclization of 1,6-Dienes: A Highly Diastereoselective Entry to Substituted Tetrahydropyrans (pages 6218–6221)

      Stefanie Roth and Christian B. W. Stark

      Article first published online: 24 JUL 2006 | DOI: 10.1002/anie.200504572

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      Widely applicable: Substituted tetrahydropyran products can be obtained in good to high yields and excellent diastereoselectivity by oxidative cyclization of 1,6-dienes (see scheme, PG=protecting group). In situ generated ruthenium tetroxide (1–5 mol %) serves as a catalyst and sodium periodate on wet silica serves as a terminal oxidant. The conversion of a cyclization product into a synthetically useful δ-lactone building block is also presented.

    30. Hydrogen-Bonded Hexamers Self-Assemble as Spherical and Tubular Superstructures on the Sub-Micron Scale (pages 6221–6224)

      Michael W. Heaven, Gareth W. V. Cave, Robert M. McKinlay, Jochen Antesberger, Scott J. Dalgarno, Praveen K. Thallapally and Jerry L. Atwood

      Article first published online: 25 JUL 2006 | DOI: 10.1002/anie.200600671

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      Six packs: Hydrogen-bonded pyrogallol[4]arene hexameric nanocapsules self-assemble into spheres (A; see picture), tubules, and combinations of both (B) on the sub-micron scale. These assemblies were characterized by using dynamic light scattering, scanning electron microscopy, transmission electron microscopy (see inset), and atomic force microscopy techniques.

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    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Book Reviews
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    7. Minireview
    8. Review
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      Preview: Angew. Chem. Int. Ed. 37/2006 (page 6229)

      Article first published online: 11 SEP 2006 | DOI: 10.1002/anie.200690127

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