Angewandte Chemie International Edition

Cover image for Vol. 47 Issue 6

January 25, 2008

Volume 47, Issue 6

Pages 987–1151

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Essay
    9. Review
    10. Communications
    11. Preview
    1. Cover Picture: Self-Organization of Electroactive Materials: A Head-to-Tail Donor–Acceptor Supramolecular Polymer (Angew. Chem. Int. Ed. 6/2008) (page 987)

      Gustavo Fernández, Emilio M. Pérez, Luis Sánchez and Nazario Martín

      Version of Record online: 21 JAN 2008 | DOI: 10.1002/anie.200890015

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      Fullerenes do the conga Fullerenes and their derivatives are widely used as electron-acceptor moieties in organic photovoltaics. In their Communication on pp. 1094 ff. N. Martín and co-workers describe the synthesis and self-recognition of a monomer featuring both a receptor for [60]fullerene (based on the electron-donor exTTF) and a C60 derivative. The monomers link head-to-tail to form linear oligomers and provide a new approach for the organization of electroactive donor–acceptor fragments.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Essay
    9. Review
    10. Communications
    11. Preview
    1. Inside Cover: Multiple C[BOND]H Activations To Construct Biologically Active Molecules in a Process Completely Free of Organohalogen and Organometallic Components (Angew. Chem. Int. Ed. 6/2008) (page 988)

      Bi-Jie Li, Shi-Liang Tian, Zhao Fang and Zhang-Jie Shi

      Version of Record online: 21 JAN 2008 | DOI: 10.1002/anie.200890016

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      Palladium-catalyzed C[BOND]H activation is employed in a novel, efficient synthesis of carbazoles and their derivatives using cross dehydrogenative arylation and Buchwald's C[BOND]N formation. As described by Z.-J. Shi and co-workers in the Communication on page 1115 ff., this methodology requires no prefunctionalization of arene starting materials and proceeds without halide or organometallic reagents.

  3. Graphical Abstract

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

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

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Essay
    9. Review
    10. Communications
    11. Preview
    1. Infrared Spectroscopy and Ab Initio Theory of Isolated H5O2+: From Buckets of Water to the Schrödinger Equation and Back (pages 1008–1011)

      Gereon Niedner-Schatteburg

      Version of Record online: 27 DEC 2007 | DOI: 10.1002/anie.200703555

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      Symmetric and asymmetric at a time: The infrared spectrum of the H5O2+ ion, which was only attained a few years ago by demanding supersonic jet expansion experiments, can now be simulated with elaborate theoretical methods. Naked H5O2+ transfers a proton exactly as predicted for fully hydrated H5O2+. A gap in the description of proton diffusion in water which was begun over 200 years ago has thus been closed.

    2. Catching the Rainbow: Light Harvesting in Dye-Sensitized Solar Cells (pages 1012–1014)

      Neil Robertson

      Version of Record online: 27 DEC 2007 | DOI: 10.1002/anie.200704538

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      Brand new combined harvesters: The development of low-cost dyes for photovoltaic systems which harvest solar radiation (spectrum shown) over a broad spectral range has proven difficult. Cosensitization using more than one dye (for example JK2 and TT1 in picture) is an emerging method to extend the spectral coverage, and may lead to higher energy-conversion efficiencies.

  7. Essay

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Essay
    9. Review
    10. Communications
    11. Preview
    1. Hugo (Ugo) Schiff, Schiff Bases, and a Century of β-Lactam Synthesis (pages 1016–1020)

      Thomas T. Tidwell

      Version of Record online: 19 NOV 2007 | DOI: 10.1002/anie.200702965

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      Schiff—the man and the base: Hugo Schiff (1834–1915) studied with Friedrich Wöhler in Germany, but because of his liberal views spent almost his entire career in Italy, where he prepared and characterized Schiff bases (imines) and made many other chemical investigations. His scientific career spanned more than 60 years, and he lived to see the utilization of Schiff bases in [2+2] cycloadditions with ketenes to form β-lactams.

  8. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Essay
    9. Review
    10. Communications
    11. Preview
    1. Diamonds are a Chemist's Best Friend: Diamondoid Chemistry Beyond Adamantane (pages 1022–1036)

      Hartmut Schwertfeger, Andrey A. Fokin and Peter R. Schreiner

      Version of Record online: 14 DEC 2007 | DOI: 10.1002/anie.200701684

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      Diamondoids are forever: The increasing availability of diamondoids in large amounts from crude oil opens the door to a virtually unstudied class of carbon-rich materials. These diamond nanostructures not only have well-defined structures but also represent the most stable form of hydrocarbons on the nanometer scale. Their functionalization and characterization has resulted in compounds that are ready for testing as pharmaceuticals, coatings, polymers, molecular junctions, and electronic devices.

  9. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Essay
    9. Review
    10. Communications
    11. Preview
    1. Highly Stable Giant Supramolecular Vesicles Composed of 2D Hydrogen-Bonded Sheet Structures of Guanosine Derivatives (pages 1038–1041)

      Isao Yoshikawa, Jun Sawayama and Koji Araki

      Version of Record online: 21 NOV 2007 | DOI: 10.1002/anie.200704535

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      Stabilized net: A molecular design approach to protect a 2D hydrogen-bonding network with nonpolar shielding layers has allowed the fabrication of micrometer-scale supramolecular vesicles in water (see picture). These hydrogen-bond-directed giant vesicles and their dispersions in aqueous media show high stability under various conditions.

    2. A Multi-Dimensional Microporous Silicate That Is Isomorphous to Zeolite MCM-68 (pages 1042–1046)

      Yoshihito Koyama, Takuji Ikeda, Takashi Tatsumi and Yoshihiro Kubota

      Version of Record online: 28 DEC 2007 | DOI: 10.1002/anie.200704222

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      Hot and steamy cages: The gel composition for MCM-68 typically obtained by hydrothermal methods is changed by steam-assisted crystallization and results in the formation of the highly crystalline pure silica analogue YNU-2P (see picture). The crystal structure of this compound indicates the presence of significant site defects.

    3. Transient X-ray Diffraction Reveals Global and Major Reaction Pathways for the Photolysis of Iodoform in Solution (pages 1047–1050)

      Jae Hyuk Lee, Joonghan Kim, Marco Cammarata, Qingyu Kong, Kyung Hwan Kim, Jungkweon Choi, Tae Kyu Kim, Michael Wulff and Hyotcherl Ihee

      Version of Record online: 28 DEC 2007 | DOI: 10.1002/anie.200704150

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      The structural dynamics of the photodissociation of iodoform in methanol (see picture: H blue, C green, I violet) are revealed by means of time-resolved X-ray diffraction in solution (also called transient X-ray liquidography because of its analogy to crystallography). While spectroscopic studies suggest the existence of isoiodoform, no signals are observed for this intermediate species in time-resolved diffraction experiments performed using time delays between 100 ps and 3 μs.

    4. Rapid Detection of S-Adenosyl Homocysteine Using Self-Assembled Optical Diffraction Gratings (pages 1051–1053)

      Ghanashyam Acharya, Chun-Li Chang, David P. Holland, David H. Thompson and Cagri A. Savran

      Version of Record online: 28 DEC 2007 | DOI: 10.1002/anie.200703222

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      I saw the SAH: Clinically relevant concentrations of S-adenosyl homocysteine (SAH) can be rapidly detected using self-assembled diffraction gratings. SAH bound to antibody-conjugated (Ab) microbeads (see picture) and then incubated with a gold chip functionalized with SAH-specific aptamer in alternating line patterns produces gratings that are detected by optical diffraction intensity measurements (detection limit: 64 pmol L−1).

    5. Carboxylic Acid Enriched Nanospheres of Semiconductor Nanorods for Cell Imaging (pages 1054–1057)

      Leyu Wang, Peng Li, Jie Zhuang, Feng Bai, Jing Feng, Xiyun Yan and Yadong Li

      Version of Record online: 20 DEC 2007 | DOI: 10.1002/anie.200703720

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      A cure for hydrophobia: Monodisperse semiconductor nanorods are synthesized using nitrates as precursors. The surface modification of these hydrophobic nanocrystals is accomplished through encapsulation with a carboxylic acid enriched polymer (see TEM images), which leads to hydrophilic, bioconjugatable nanospheres for use in multicolor biolabeling applications.

    6. Structure Calculation of an Elastic Hydrogel from Sonication of Rigid Small Molecule Components (pages 1058–1062)

      Kirsty M. Anderson, Graeme M. Day, Martin J. Paterson, Peter Byrne, Nigel Clarke and Jonathan W. Steed

      Version of Record online: 28 DEC 2007 | DOI: 10.1002/anie.200703785

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      Making plans for hydrogels: Calculations successfully predict the molecular structure of a robust hydrogel. Melamine and uric acid cocrystallize with water upon sonication, and using experimental data, the minimized structure (see picture) was calculated and successfully compared with powder X-ray diffraction data of the xerogel.

    7. Ultrasound Switch and Thermal Self-Repair of Morphology and Surface Wettability in a Cholesterol-Based Self-Assembly System (pages 1063–1067)

      Junchen Wu, Tao Yi, Tianmin Shu, Mengxiao Yu, Zhiguo Zhou, Miao Xu, Yifeng Zhou, Huijun Zhang, Jiantao Han, Fuyou Li and Chunhui Huang

      Version of Record online: 20 DEC 2007 | DOI: 10.1002/anie.200703946

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      Sound effects: The morphologies and surface properties of a cholesterol-based assembly with two hydrogen-bond sites per molecule can be controlled by ultrasound stimuli and restored by a thermal process. The cooperation competition of intra- and intermolecular hydrogen bonds and hydrophobic interactions, regulated by sonication or thermal processes, are suggested to be the main contributions toward the self-assembly (see schematic of gelation process and wettability tests).

    8. Detection of a Radical Cation of an NADH Analogue in Two-Electron Reduction of a Protonated p-Quinone Derivative by an NADH Analogue (pages 1068–1071)

      Junpei Yuasa, Shunsuke Yamada and Shunichi Fukuzumi

      Version of Record online: 28 DEC 2007 | DOI: 10.1002/anie.200704136

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      An electron-transfer pathway is preferred to a direct hydride-transfer pathway in two-electron reduction of protonated 1-(p-tolylsulfinyl)-2,5-benzoquinone by the NADH analogue 10-methyl-9,10-dihydroacridine, as has been demonstrated for the first time by ESR detection of the resulting radical cation of the acridine derivative (see picture).

    9. A Hydrodynamically Focused Stream as a Dynamic Template for Site-Specific Electrochemical Micropatterning of Conducting Polymers (pages 1072–1075)

      Shuang Hou, Shutao Wang, Zeta T. F. Yu, Nicole Q. M. Zhu, Kan Liu, Jing Sun, Wei-Yu Lin, Clifton K.-F. Shen, Xiaohong Fang and Hsian-Rong Tseng

      Version of Record online: 4 JAN 2008 | DOI: 10.1002/anie.200704264

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      Working patterns: Size-controllable electrochemical deposition of conducting polymer micropatterns across individually addressable electrode junction pairs (inset) is achieved with a hydrodynamically focused laminar stream in a microfluidic setting (see picture). Such a focused stream can be used as a dynamic template for sequential production of sensor arrays capable of detecting extremely small quantities of analytes.

    10. Two-Dimensional Tiling by Rubrene Molecules Self-Assembled in Supramolecular Pentagons, Hexagons, and Heptagons on a Au(111) Surface (pages 1076–1079)

      Marina Pivetta, Marie-Christine Blüm, François Patthey and Wolf-Dieter Schneider

      Version of Record online: 28 DEC 2007 | DOI: 10.1002/anie.200704479

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      Tiling patterns: Rubrene (C42H28) molecules self-assemble on a gold surface to create a two-dimensional tiling with a combination of slightly distorted supramolecular pentagons, hexagons, and heptagons. Both periodic and nonperiodic tessellations are observed, as well as circular singularities in extended honeycomb domains, formed by the replacement of a ring of twelve hexagons by six pentagon-heptagon pairs.

    11. Metal–Organic Nanoporous Structures with Anisotropic Photoluminescence and Magnetic Properties and Their Use as Sensors (pages 1080–1083)

      Bogdan V. Harbuzaru, Avelino Corma, Fernando Rey, Pedro Atienzar, Jose L. Jordá, Hermenegildo García, Duarte Ananias, Luis D. Carlos and João Rocha

      Version of Record online: 8 JAN 2008 | DOI: 10.1002/anie.200704702

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      Shining bright: Porous metal–organic framework materials are important owing to their potential applications as sensors. A new family of nanoporous, multifunctional rare-earth metal–organic materials displays emission quantum yields and efficiencies that are the highest reported for solid-state Eu3+ compounds with organic ligands and magnetic properties. The picture shows [Gd,Eu]- and [Tb]-containing materials under UV light and interacting with a magnet.

    12. Total Synthesis and Structure Assignment of the Anthrone C-Glycoside Cassialoin (pages 1084–1087)

      Yasuhito Koyama, Ryo Yamaguchi and Keisuke Suzuki

      Version of Record online: 28 DEC 2007 | DOI: 10.1002/anie.200704625

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      Configuration confirmed: The first total synthesis and structure assignment of the anthrone C-glycoside cassialoin (1) have been achieved by exploiting an isoxazole-containing stereogenic α-ketol and a subsequent intramolecular redox reaction (see retrosynthetic analysis; MOM = methoxymethyl).

    13. Catalytic Asymmetric Alkylation of Aldehydes with Grignard Reagents (pages 1088–1090)

      Yusuke Muramatsu and Toshiro Harada

      Version of Record online: 4 JAN 2008 | DOI: 10.1002/anie.200704963

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      Added benefits: Grignard reagents can be employed in the asymmetric alkylation of aldehydes by using a titanium(IV) catalyst derived from binol in the presence of excess titanium tetraisopropoxide (see scheme). The reaction proceeds with a low catalyst loading (2 mol %) and exhibits high enantioselectivity for both aromatic and unsaturated aldehydes and for both alkyl and aryl Grignard reagents.

    14. Regioselective Aliphatic Retro-[1,4]-Brook Rearrangements (pages 1091–1093)

      Yuji Mori, Yutaka Futamura and Kazumi Horisaki

      Version of Record online: 4 JAN 2008 | DOI: 10.1002/anie.200702539

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      A turn-up for the Brook: The relative ease of silyl migration in the aliphatic retro-Brook rearrangements of α,γ-disilyloxy organolithium compounds (see scheme) has been revealed for the first time to be [1,2]≪[1,4]. The increasing size of the silyloxy group at the γ position relative to that at the α position induces higher [1,4] selectivity.

      Corrected by:

      Corrigendum: Regioselective Aliphatic Retro-[1,4]-Brook Rearrangements

      Vol. 47, Issue 11, 1982, Version of Record online: 22 FEB 2008

    15. Self-Organization of Electroactive Materials: A Head-to-Tail Donor–Acceptor Supramolecular Polymer (pages 1094–1097)

      Gustavo Fernández, Emilio M. Pérez, Luis Sánchez and Nazario Martín

      Version of Record online: 8 NOV 2007 | DOI: 10.1002/anie.200703049

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      Fullerenes do the conga! Synthesis and self-recognition of a monomer featuring a specially designed receptor for [60]fullerene are described. The monomer self-assembles in a head-to-tail fashion through π–π interactions, thus forming a linear oligomeric species in solution (see image). The formation of this redox-amphoteric supramolecular polymer represents a new approach to the controlled organization of electroactive materials.

    16. Practical Implications of Boron-to-Zinc Transmetalation for the Catalytic Asymmetric Arylation of Aldehydes (pages 1098–1101)

      Ciril Jimeno, Sonia Sayalero, Torstein Fjermestad, Gisela Colet, Feliu Maseras and Miquel A. Pericàs

      Version of Record online: 28 DEC 2007 | DOI: 10.1002/anie.200703103

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      Faster than believed: Transmetalation from aryl boronic acids and triaryl boroxines to diethylzinc takes place within minutes following a two-step, low-energy pathway (see picture), according to density functional calculations and reaction microcalorimetry measurements. The experimental conditions for a practical, atom-economical, and highly enantioselective catalytic arylation of a variety of aldehydes have been developed from these data.

    17. Comparative Properties of Insulin-like Growth Factor 1 (IGF-1) and [Gly7D-Ala]IGF-1 Prepared by Total Chemical Synthesis (pages 1102–1106)

      Youhei Sohma, Brad L. Pentelute, Jonathan Whittaker, Qin-xin Hua, Linda J. Whittaker, Michael A. Weiss and Stephen B. H. Kent

      Version of Record online: 27 DEC 2007 | DOI: 10.1002/anie.200703521

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      Chemistry for biology: IGF-1 and [Gly7D-Ala]IGF-1 have been prepared by a total chemical synthesis and their folding and receptor-binding properties compared (see scheme). This approach facilitates the introduction of nonstandard amino acids whose biosynthetic incorporation is difficult or not feasible and thus promises to lead to a new generation of structure–activity studies of potential interest in the treatment of cancer and diabetes mellitus.

    18. Donor–Acceptor Cyclopropanes as Three-Carbon Components in a [4+3] Cycloaddition Reaction with 1,3-Diphenylisobenzofuran (pages 1107–1110)

      Olga A. Ivanova, Ekaterina M. Budynina, Yuri K. Grishin, Igor V. Trushkov and Pavel V. Verteletskii

      Version of Record online: 4 JAN 2008 | DOI: 10.1002/anie.200704438

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      Dienophiles with a difference: 2-Aryl 1,1-bis(alkoxycarbonyl) cyclopropanes undergo the title reaction under the catalysis of ytterbium triflate (Yb(OTf)3) in excellent yield (see scheme). Under mild reaction conditions, the major product is the less stable exo isomer. At higher temperatures, the endo isomer is obtained exclusively, as the exo cycloadduct decomposes through cycloreversion.

    19. The Selenium-Based Hexameric Macrocycle [(Se[DOUBLE BOND])P(μ-NtBu)2P(μ-Se)]6 (pages 1111–1114)

      Silvia González-Calera, Dana J. Eisler, James V. Morey, Mary McPartlin, Sanjay Singh and Dominic S. Wright

      Version of Record online: 2 JAN 2008 | DOI: 10.1002/anie.200703981

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      Head-to-Tail: The Wurtz reaction of the dimer [(Cl)(Se[DOUBLE BOND])P(μ-NtBu)]2 (1) with sodium metal gives the inorganic macrocycle [(Se[DOUBLE BOND])P(μ-NtBu)2P(μ-Se)]6 (2), arising from cyclization of a selenium-centered nucleophilic intermediate. The inorganic macrocyclic backbone contains alternating PIII and PV centers and possesses an 8.2-Å-diameter cavity.

    20. Multiple C[BOND]H Activations To Construct Biologically Active Molecules in a Process Completely Free of Organohalogen and Organometallic Components (pages 1115–1118)

      Bi-Jie Li, Shi-Liang Tian, Zhao Fang and Zhang-Jie Shi

      Version of Record online: 5 NOV 2007 | DOI: 10.1002/anie.200704092

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      Step by step: Highly selective cross dehydrogenative arylation of acetanilides was developed to construct biaryls under mild condition. With this method, different aryl C[BOND]H bonds were activated in sequential reactions to construct functionalized carbazoles (see scheme), which are present as key structural units in various biological molecules and organic optical materials.

    21. Asymmetric Counteranion-Directed Catalysis for the Epoxidation of Enals (pages 1119–1122)

      Xingwang Wang and Benjamin List

      Version of Record online: 27 DEC 2007 | DOI: 10.1002/anie.200704185

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      A new mode of chiral anion catalysis: A powerful chiral-counteranion strategy for catalytic asymmetric epoxidations using the newly discovered catalyst 1 has been applied to the epoxidation of α,β-unsaturated aldehydes together with tert-butyl hydroperoxide as the oxidant (see scheme). Remarkably, this system provides the corresponding epoxides in high diastereo- and enantioselectivity for both di- and trisubstituted enals.

    22. The Largest 15N–15N Coupling Constant Across an NHN Hydrogen Bond (pages 1123–1126)

      Mariusz Pietrzak, Andrew C. Try, Bruno Andrioletti, Jonathan L. Sessler, Pavel Anzenbacher Jr. and Hans-Heinrich Limbach

      Version of Record online: 27 DEC 2007 | DOI: 10.1002/anie.200704411

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      Tug of war: Treatment of the doubly 15N-labeled anion receptor 6-nitro-2,3-dipyrrol-2-ylquinoxaline with solid sodium hydride in CD2Cl2/[D6]DMSO leads to the monodeprotonated anion (see picture). The NMR data indicate the formation of a very strong intramolecular NHN hydrogen bond, with a scalar 15N–15N coupling constant of 16.5 Hz, the largest value observed to date.

    23. Hydrogenation of Carbon Dioxide is Promoted by a Task-Specific Ionic Liquid (pages 1127–1129)

      Zhaofu Zhang, Ye Xie, Wenjing Li, Suqin Hu, Jinliang Song, Tao Jiang and Buxing Han

      Version of Record online: 18 DEC 2007 | DOI: 10.1002/anie.200704487

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      A basic hydrogenation catalyst: The combination of a basic ionic liquid (IL) and a supported ruthenium complex catalyzes the hydrogenation of CO2 with satisfactory activity and selectivity (see scheme). The resulting formic acid is easily collected and the ionic liquid and catalyst can be reused directly after an easy separation step.

    24. Confirmation of the Stereostructure of (+)-Cytostatin by Fluorous Mixture Synthesis of Four Candidate Stereoisomers (pages 1130–1133)

      Won-Hyuk Jung, Sabrina Guyenne, Concepción Riesco-Fagundo, John Mancuso, Shuichi Nakamura and Dennis P. Curran

      Version of Record online: 3 JAN 2008 | DOI: 10.1002/anie.200704893

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      Mix and match: Four closely related candidate isomers for cytostatin have been synthesized by using the technique of fluorous mixture synthesis. Comparison of NMR, thin-layer chromatography, and optical rotation data enabled the three isomers that were not cytostatin to be identified. Thus, by a process of elimination (disproof), the isomer corresponding to cytostatin was determined, and the 4S,5S,6S,9S,10S,11S configuration confirmed.

    25. Allylation of Ketones with a Ferrocene-Based Planar Chiral Lewis Acid (pages 1134–1137)

      Ramez Boshra, Ami Doshi and Frieder Jäkle

      Version of Record online: 28 DEC 2007 | DOI: 10.1002/anie.200704687

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      Flat, like your hand: The heteronuclear bidentate Lewis acid 1,2-Fc(BMeCl)(SnMe2Cl) is readily resolved into its constituent enantiomers through highly stereoselective complexation with N-methylpseudoephedrine. The resulting planar chiral Lewis acids show optical purities greater than 97 % and, upon conversion to the respective allylborane derivatives (see scheme), rapidly add to ketones with enantiomeric excess of up to 80 %.

    26. Highly Efficient Ruthenium(II) Porphyrin Catalyzed Amidation of Aldehydes (pages 1138–1140)

      Joyce Wei Wei Chang and Philip Wai Hong Chan

      Version of Record online: 28 DEC 2007 | DOI: 10.1002/anie.200704695

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      H to N: The first example of a mild, highly efficient C[BOND]H bond amidation catalyzed by ruthenium(II) porphyrin complexes uses PhI[DOUBLE BOND]NTs as the nitrogen source for installing the amide bond functionality in a wide variety of aldehydes (see scheme). The protocol is chemoselective, with the new C[BOND]N bond forming only at the acyl C[BOND]H bond, even in aldehyde substrates containing other functional groups.

    27. Generation and Coordinating Properties of a Carbene Bearing a Phosphorus Ylide: An Intensely Electron-Donating Ligand (pages 1141–1144)

      Shin-ya Nakafuji, Junji Kobayashi and Takayuki Kawashima

      Version of Record online: 4 JAN 2008 | DOI: 10.1002/anie.200704746

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      A generous giver: Rh and Pd complexes of an ylide-substituted carbene were synthesized. The carbonyl stretching vibration of the Rh complex (see picture; Rh purple, C turquoise, N blue, O red, P orange, Cl green) was observed at the lowest wavenumber of all cis-[RhCl(CO)2(carbene)] complexes known to date, which indicates that this is the strongest known electron-donating carbene.

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

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