Angewandte Chemie International Edition

Cover image for Vol. 48 Issue 30

July 13, 2009

Volume 48, Issue 30

Pages 5381–5553

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Cover Picture: An Enantiomerically Pure Alleno-Acetylenic Macrocycle: Synthesis and Rationalization of Its Outstanding Chiroptical Response (Angew. Chem. Int. Ed. 30/2009) (page 5381)

      José Lorenzo Alonso-Gómez, Pablo Rivera-Fuentes, Nobuyuki Harada, Nina Berova and François Diederich

      Article first published online: 8 JUL 2009 | DOI: 10.1002/anie.200990154

      Thumbnail image of graphical abstract

      Enantiopure, Shape-Persistent alleno-acetylenic macrocycles are prepared from optically pure 1,3-diethynylallene building blocks, as F. Diederich et al. report in their Communication on page 5545 ff. These macrocycles with their crown geometry and chiral C28 backbone are not only aesthetically pleasing, they also display unusually intense Cotton effects in their circular dichroism spectra, which arise from the unique interplay of the shape-persistent geometry and electronic properties.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Inside Cover: 1,1,8,8-Tetramethyl[8](2,11)teropyrenophane: Half of an Aromatic Belt and a Segment of an (8,8) Single-Walled Carbon Nanotube (Angew. Chem. Int. Ed. 30/2009) (page 5382)

      Bradley L. Merner, Louise N. Dawe and Graham J. Bodwell

      Article first published online: 8 JUL 2009 | DOI: 10.1002/anie.200990155

      Thumbnail image of graphical abstract

      Large, nonplanar PAHs (polycyclic aromatic hydrocarbons) are important because they can be viewed as discrete substructures of the newer allotropes of carbon nanotubes. In their Communication on page 5487 ff., G. J. Bodwell and co-workers present a concise synthesis of a (2,11)teropyrenophane, which features a 36-carbon polynuclear aromatic system. Such a system structurally resembles a segment of an (8,8) single-walled carbon nanotube.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Graphical Abstract: Angew. Chem. Int. Ed. 30/2009 (pages 5385–5395)

      Article first published online: 8 JUL 2009 | DOI: 10.1002/anie.200990156

  4. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Tsutomu Katsuki (page 5398)

      Article first published online: 16 JUN 2009 | DOI: 10.1002/anie.200902602

      Thumbnail image of graphical abstract

      “My most exciting discovery to date has been asymmetric epoxidation of allylic alcohols in the Sharpless lab. If I wasn't a scientist, I would be a high-school teacher. …” This and more about Tsutomu Katsuki can be found on page 5398.

  6. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Solution Processing of Inorganic Materials.Edited by David B. Mitzi. (page 5399)

      Michael Wark

      Article first published online: 8 JUL 2009 | DOI: 10.1002/anie.200902905

      Thumbnail image of graphical abstract

      John Wiley & Sons, Hoboken 2009. 498 pp., hardcover € 109.00.—ISBN 978–0470406656

  7. Highlights

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

      New Strategies for Synthesizing Short Sections of Carbon Nanotubes (pages 5400–5402)

      Brian D. Steinberg and Lawrence T. Scott

      Article first published online: 28 MAY 2009 | DOI: 10.1002/anie.200901025

      Thumbnail image of graphical abstract

      Harbingers of single-chirality nanotubes: Lessons learned from recent syntheses of cyclophanes with record numbers of benzene rings embedded in the macrocycle (see picture) have brought chemists closer to the goal of obtaining structurally uniform single-walled carbon nanotubes made-to-order. The syntheses of the cyclophanes rely on the aromatization of less-strained dihydroaromatic ring systems in the last step to build in the strain.

    2. Nanotube Synthesis

      Growth of Single-Walled Carbon Nanotubes without a Metal Catalyst—A Surprising Discovery (pages 5403–5404)

      Andreas Hirsch

      Article first published online: 3 JUN 2009 | DOI: 10.1002/anie.200901980

      Thumbnail image of graphical abstract

      SiO2nanoparticles alone can catalyze the formation of single-walled carbon nanotubes (SWNTs). Since transition-metal catalysts are not required, clean SWNT materials can be prepared whose intrinsic property profile is not obscured by metal catalyst particles.

  8. Minireview

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

      Engineering Substrate Topography at the Micro- and Nanoscale to Control Cell Function (pages 5406–5415)

      Christopher J. Bettinger, Robert Langer and Jeffrey T. Borenstein

      Article first published online: 2 JUN 2009 | DOI: 10.1002/anie.200805179

      Thumbnail image of graphical abstract

      Grounded: Substrate nanotopography is known to profoundly influence the behavior of cells both in vitro and in vivo. Recent developments have demonstrated the use of engineered synthetic substrates to control complex cell function, including differentiation and tissue formation. The fluorescent micrograph in the picture depicts a multicellular structure of endothelial cells that was assembled using substrates with synthetic nanotopography.

  9. Review

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

      Nanogels as Pharmaceutical Carriers: Finite Networks of Infinite Capabilities (pages 5418–5429)

      Alexander V. Kabanov and Serguei V. Vinogradov

      Article first published online: 27 JUN 2009 | DOI: 10.1002/anie.200900441

      Thumbnail image of graphical abstract

      Drug protection: Nanogels—swollen nanosized networks of hydrophilic neutral or ionic polymer chains—can spontaneously incorporate low-molecular-mass drugs or biomacromolecules such as oligonucleotides, siRNA, DNA, and proteins. Numerous chemical functionalities can be employed for the introduction of imaging molecules and the targeted release of drugs (see picture).

  10. Communications

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

      Osmapyridine and Osmapyridinium from a Formal [4+2] Cycloaddition Reaction (pages 5430–5434)

      Bin Liu, Huijuan Wang, Hujun Xie, Birong Zeng, Jinxiang Chen, Jun Tao, Ting Bin Wen, Zexing Cao and Haiping Xia

      Article first published online: 3 APR 2009 | DOI: 10.1002/anie.200900998

      Thumbnail image of graphical abstract

      Metalla-cycloaddition: An unprecedented formal [4+2] cycloaddition reaction takes place when osmium hydrido alkenylcarbyne 1 reacts with acetonitrile to afford the first metallapyridinium complex 2 in high yield (see scheme). Deprotonation of 2 gives the first osmapyridine compound 3. Treatment of 3 with HBF4 can regenerate 2 in almost quantitative yield.

    2. Carbon Nanotubes

      Efficient Separation of (6,5) Single-Walled Carbon Nanotubes Using a “Nanometal Sinker” (pages 5435–5438)

      Yuichi Kato, Yasuro Niidome and Naotoshi Nakashima

      Article first published online: 3 JUN 2009 | DOI: 10.1002/anie.200900651

      Thumbnail image of graphical abstract

      Sort it out! Density-gradient ultracentrifugation is used to separate single-walled carbon nanotubes (SWNTs) of a single chirality. A “nanometal sinker” (AuCl4 ions) adsorbs onto specific SWNTs and allows the separation of adsorbed SWNTs and nonfunctionlized SWNTs (see picture). (6,5) SWNTs have been successfully separated from as-prepared SWNTs in a process termed “SWNT chirality fishing”.

    3. Photoconductive Structures

      A Photoconductive Covalent Organic Framework: Self-Condensed Arene Cubes Composed of Eclipsed 2D Polypyrene Sheets for Photocurrent Generation (pages 5439–5442)

      Shun Wan, Jia Guo, Jangbae Kim, Hyotcherl Ihee and Donglin Jiang

      Article first published online: 11 MAY 2009 | DOI: 10.1002/anie.200900881

      Thumbnail image of graphical abstract

      On again, off again: A pyrene-based covalent organic framework (see structure: blue pyrene, white B, red O) facilitates exciton migration and carrier transportation, harvests visible-light photons, and responds quickly to irradiation with light to enable the generation of a significant photocurrent. The framework is capable of repetitive photocurrent switching with a large on–off ratio.

    4. Conjugated Polymers

      Controlling Rigidity and Planarity in Conjugated Polymers: Poly(3,4-ethylenedithioselenophene) (pages 5443–5447)

      Yair H. Wijsboom, Asit Patra, Sanjio S. Zade, Yana Sheynin, Mao Li, Linda J. W. Shimon and Michael Bendikov

      Article first published online: 2 JUN 2009 | DOI: 10.1002/anie.200901231

      Thumbnail image of graphical abstract

      Staying on a plane: Even small substituents on the backbone of conjugated polymers can cause them to twist significantly, lowering conjugation and leading to wider band gaps. Oligo- and polyselenophenes are more rigid than their thiophene analogues, and can maintain their planarity and low band gap with substituents that otherwise cause considerable twisting. The picture shows two selenophene dimers; Se magenta, S yellow.

    5. Fused Polycycles

      One-Step Synthesis of the Benzocyclo[penta- to octa-]isoindole Core (pages 5448–5451)

      Yimin Hu, Chenli Yu, Dong Ren, Qiong Hu, Lidong Zhang and Dong Cheng

      Article first published online: 19 MAY 2009 | DOI: 10.1002/anie.200901246

      Thumbnail image of graphical abstract

      Three in one go: Unactivated dienes containing a cycloalkenyl moiety reacted with a range of substituted aryl halides in the presence of Pd(OAc)2/PPh3 to afford fused polycyclic heterocycles (see scheme). Three carbon–carbon bonds are formed in this domino reaction, which involves highly regioselective C[BOND]C coupling and C[BOND]H functionalization steps. DMF=N,N-dimethylformamide; Bn=benzyl, Ts=p-toluenesulfonyl.

    6. Polyoxometalate Formation

      Nucleation Mechanisms of Molecular Oxides: A Study of the Assembly–Dissassembly of [W6O19]2− by Theory and Mass Spectrometry (pages 5452–5456)

      Laia Vilà-Nadal, Antonio Rodríguez-Fortea, Li-Kai Yan, Elizabeth F. Wilson, Leroy Cronin and Josep M. Poblet

      Article first published online: 18 JUN 2009 | DOI: 10.1002/anie.200901348

      Thumbnail image of graphical abstract

      Step by step: The combined use of ESI mass spectrometry and complementary DFT approaches allows the proposal of a formation mechanism for the Lindqvist anion. The mechanism is based on successive aggregation steps of hydrogentungstate anion as the “building block” with subsequent protonation and water condensation. The Lindqvist anion is formed after five steps.

    7. Molecular Conformation

      Synthesis and Structure of Stereoisomeric Multivicinal Hexafluoroalkanes (pages 5457–5460)

      Luke Hunter, Peer Kirsch, Alexandra M. Z. Slawin and David O'Hagan

      Article first published online: 23 JUN 2009 | DOI: 10.1002/anie.200901956

      Thumbnail image of graphical abstract

      Rational expectations: Molecules containing six contiguous fluorine atoms along a carbon backbone have been synthesized in a stereocontrolled manner. X-ray crystallography shows that the fluoroalkane can adopt a helical or a zigzag shape depending on the stereochemical pattern (see structures). These findings are rationalized by simple stereochemical effects associated with C[BOND]F bonds.

    8. C[BOND]H Activation

      Selective Synthesis of Osmanaphthalene and Osmanaphthalyne by Intramolecular C[BOND]H Activation (pages 5461–5464)

      Bin Liu, Hujun Xie, Huijuan Wang, Liqiong Wu, Qianyi Zhao, Jinxiang Chen, Ting Bin Wen, Zexing Cao and Haiping Xia

      Article first published online: 18 JUN 2009 | DOI: 10.1002/anie.200902238

      Thumbnail image of graphical abstract

      Bisosmanaphthalene 2 and osmanaphthalyne 3 can conveniently be synthesized selectively and in high yield from osmium hydride–alkenylcarbyne 1 by intramolecular C[BOND]H activation under an inert or oxidizing atmosphere (N2 or O2, respectively). The transformation of bisosmanaphthalene 2 into osmanaphthalyne 3 represents the first conversion from metallabenzene into metallabenzyne.

    9. Supramolecular Chemistry

      Octadehydrodibenzo[12]annulene-Based Organogels: Two Methyl Ester Groups Prevent Crystallization and Promote Gelation (pages 5465–5469)

      Ichiro Hisaki, Hajime Shigemitsu, Yuu Sakamoto, Yasuchika Hasegawa, Yasuo Okajima, Kazunori Nakano, Norimitsu Tohnai and Mikiji Miyata

      Article first published online: 26 MAY 2009 | DOI: 10.1002/anie.200900501

      Thumbnail image of graphical abstract

      A boomerang-shaped organic gelator, a dehydrobenzo[12]annulene derivative with two methyl ester groups (see picture), successfully forms an organogel in various organic solvents.

    10. Helical Structures

      One-Step Construction of Five Successive Rings by Rhodium-Catalyzed Intermolecular Double [2+2+2] Cycloaddition: Enantioenriched [9]Helicene-Like Molecules (pages 5470–5473)

      Ken Tanaka, Naohiro Fukawa, Takeshi Suda and Keiichi Noguchi

      Article first published online: 18 JUN 2009 | DOI: 10.1002/anie.200901962

      Thumbnail image of graphical abstract

      Spiraling upwards: Enantioenriched fluorenone-containing [9]helicene-like molecules have been successfully synthesized through the formation of five successive rings by rhodium-catalyzed intermolecular double [2+2+2] cycloadditions of 2-naphthol-linked tetraynes with dialkynylketones (see scheme; cod=cycloocta-1,5-diene). Their unique crystal structures and photophysical properties have also been determined.

    11. Asymmetric Aminocatalysis

      Organocatalytic Regio- and Stereoselective Inverse-Electron-Demand Aza-Diels–Alder Reaction of α,β-Unsaturated Aldehydes and N-Tosyl-1-aza-1,3-butadienes (pages 5474–5477)

      Bo Han, Zhao-Quan He, Jun-Long Li, Rui Li, Kun Jiang, Tian-Yu Liu and Ying-Chun Chen

      Article first published online: 24 JUN 2009 | DOI: 10.1002/anie.200902216

      Thumbnail image of graphical abstract

      Dienamines formed in situ from a chiral secondary amine and an α,β-unsaturated aldehyde undergo the highly α-regioselective title reaction to give densely functionalized piperidine derivatives with excellent enantioselectivity (see scheme). The products were converted into a variety of versatile cyclic frameworks. Ts=4-toluenesulfonyl.

    12. Natural Product Synthesis

      Asymmetric Total Synthesis of Soraphen A: A Flexible Alkyne Strategy (pages 5478–5481)

      Barry M. Trost, Joshua D. Sieber, Wei Qian, Rajiv Dhawan and Zachary T. Ball

      Article first published online: 24 JUN 2009 | DOI: 10.1002/anie.200901907

      Thumbnail image of graphical abstract

      A triple-bond bonanza: The alkyne functional group can be a valuable handle for organic synthesis because the alkyne unit can function both as a nucleophile or as an electrophile when activated with an appropriate metal catalyst. This dual nature of the alkyne moiety has been exploitated for the concise total synthesis of the natural product soraphen A (see retrosynthesis; PMB=para-methoxybenzyl, TBS=tert-butyldimethylsilyl).

      Corrected by:

      Corrigendum: Asymmetric Total Synthesis of Soraphen A: A Flexible Alkyne Strategy

      Vol. 48, Issue 45, 8396, Article first published online: 20 OCT 2009

    13. Singlet Biradicals

      Resonance Balance Shift in Stacks of Delocalized Singlet Biradicals (pages 5482–5486)

      Akihiro Shimizu, Mikio Uruichi, Kyuya Yakushi, Hiroyuki Matsuzaki, Hiroshi Okamoto, Masayoshi Nakano, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata and Takashi Kubo

      Article first published online: 22 JUN 2009 | DOI: 10.1002/anie.200901382

      Thumbnail image of graphical abstract

      Two flavors: Intra- and intermolecular spin–spin interactions of unpaired electrons coexist and correlate in stacks of phenalenyl-based singlet biradicals. The electronic structure of the one-dimensional π–π chain is best represented by the superposition of formulas A and B in terms of the resonating valence-bond (RVB) model. Lower temperatures and higher pressures induce a resonance balance shift to the formula B.

    14. Cyclophanes

      1,1,8,8-Tetramethyl[8](2,11)teropyrenophane: Half of an Aromatic Belt and a Segment of an (8,8) Single-Walled Carbon Nanotube (pages 5487–5491)

      Bradley L. Merner, Louise N. Dawe and Graham J. Bodwell

      Article first published online: 17 MAR 2009 | DOI: 10.1002/anie.200806363

      Thumbnail image of graphical abstract

      A mind-bending compound: 1,1,8,8-Tetramethyl[8](2,11)teropyrenophane (see picture) has been synthesized in just eight steps and 10 % overall yield from dimethyl suberate. The teropyrene system and its two benzylic carbon atoms are close in structure to half of an 80-carbon atom aromatic belt (Vögtle belt) and a segment of an (8,8) single-walled carbon nanotube.

    15. Gas Adsorption

      Amorphous Molecular Organic Solids for Gas Adsorption (pages 5492–5495)

      Jian Tian, Praveen K. Thallapally, Scott J. Dalgarno, Peter B. McGrail and Jerry L. Atwood

      Article first published online: 3 JUN 2009 | DOI: 10.1002/anie.200900479

      Thumbnail image of graphical abstract

      Fixing the hole: Molecular organic compounds with large accessible internal cavities display gas-storage ability in the amorphous solid state. This finding suggests for the first time that long-range molecular order is not a prerequisite for organic molecules to be engineered as porous materials.

    16. Porphyrinoids

      Triply N-Confused Hexaphyrins: Near-Infrared Luminescent Dyes with a Triangular Shape (pages 5496–5499)

      Yong-Shu Xie, Keisuke Yamaguchi, Motoki Toganoh, Hidemitsu Uno, Masaaki Suzuki, Shigeki Mori, Shohei Saito, Atsuhiro Osuka and Hiroyuki Furuta

      Article first published online: 19 MAY 2009 | DOI: 10.1002/anie.200900596

      Thumbnail image of graphical abstract

      Getting in shape: Meso-pentafluorophenyl triply N-confused hexaphyrins have been synthesized in the free-base and oxidized forms and shown to have a triangular shape and efficient emission in the NIR region (see picture). The triangular shape is achieved by the presence of alternating confused and normal pyrrole rings. DFT calculations show that the triangular shape is more stable than a rectangular form.

    17. Synthetic Methods

      Diverse Reactivity of Zirconacyclocumulenes Derived from Coupling of Benzynezirconocenes with 1,3-Butadiynes towards Acyl Cyanides: Synthesis of Indeno[2,1-b]pyrroles or [3]Cumulenones (pages 5500–5504)

      Xiaoping Fu, Jingjin Chen, Guangyu Li and Yuanhong Liu

      Article first published online: 28 MAY 2009 | DOI: 10.1002/anie.200900951

      Thumbnail image of graphical abstract

      Versatility: Cycloaddition of carbamoyl cyanides to 1,3-butadiynes via seven-membered zirconacyclocumulenes yields dihydroindeno[2,1-b]pyrroles (see scheme, right); a C(sp2)[BOND]H bond on the aromatic substituent of the 1,3-butadiyne reactant is activated in the process. In contrast, reactions with aryl or alkyl acyl cyanides provide a stereoselective route to cis-[3]cumulenones (left).

    18. Highly Substituted Furo[3,4-d][1,2]oxazines: Gold-Catalyzed Regiospecific and Diastereoselective 1,3-Dipolar Cycloaddition of 2-(1-Alkynyl)-2-alken-1-ones with Nitrones (pages 5505–5508)

      Feng Liu, Yihua Yu and Junliang Zhang

      Article first published online: 24 JUN 2009 | DOI: 10.1002/anie.200901299

      Thumbnail image of graphical abstract

      Rapid access: A gold(I)-catalyzed 1,3-dipolar cycloaddition of 2-(1-alkynyl)-2-alken-1-ones with nitrones provides a practical, regiospecific, and stereoselective access to highly substituted fused bicyclic furo[3,4-d][1,2]oxazines under mild conditions (see scheme). These fused heterobicyclic compounds can be readily converted into furans or 3,6-dihydro-2H-1,2-oxazines in a chemoselective fashion.

    19. Host–Guest Systems

      Induced-Fit Encapsulation by a 1,3,5-Alternate Calix[6]arene (pages 5509–5512)

      Mickaël Ménand, Axel Leroy, Jérôme Marrot, Michel Luhmer and Ivan Jabin

      Article first published online: 24 JUN 2009 | DOI: 10.1002/anie.200901722

      Thumbnail image of graphical abstract

      A little bit of flexibility: Charged or neutral species can be accommodated in solution and in the solid state by the closed hydrophobic cavity of the first calix[6]arene to adopt a 1,3,5-alternate conformation (see picture, Boc=tert-butoxycarbonyl). The encapsulation involves an induced-fit process that is reminiscent of the rotation of a door and is characterized by large activation barriers for guest exchange.

    20. N-Heterocyclic Carbenes

      Direct Synthesis of Iron, Cobalt, Nickel, and Copper Complexes of N-Heterocyclic Carbenes by Using Commercially Available Metal Powders (pages 5513–5516)

      Bin Liu, Qinqin Xia and Wanzhi Chen

      Article first published online: 24 JUN 2009 | DOI: 10.1002/anie.200901850

      Thumbnail image of graphical abstract

      Move to the first row: Simple and practical synthetic methods have been developed for metal complexes of N-heterocyclic carbenes. A number of FeII, CoII, NiII, as well as divalent and mixed-valent Cu carbene complexes were obtained in good yields by treating metal powders with imidazolium salts in the presence of Ag2O or air.

    21. Carbohydrate Isomerization

      Stabilization of the Acyclic Tautomer in Reducing Carbohydrates (pages 5517–5520)

      Valeri V. Mossine, Charles L. Barnes, Deborah L. Chance and Thomas P. Mawhinney

      Article first published online: 23 JUN 2009 | DOI: 10.1002/anie.200902123

      Thumbnail image of graphical abstract

      Sweet structure: Acyclic reducing carbohydrate intermediates are typically impossible to crystallize. 1-Amino-1-deoxy-D-fructose derivatives afford an exceptional example of the keto form in the crystalline state (see structure), possibly as a consequence of an interplay between the hydrophobic microenvironment around the carbonyl group and hydrogen-bonding patterns.

    22. Biocatalysis

      Asymmetric Self- and Cross-Aldol Reactions of Glycolaldehyde Catalyzed by D-Fructose-6-phosphate Aldolase (pages 5521–5525)

      Xavier Garrabou, José A. Castillo, Christine Guérard-Hélaine, Teodor Parella, Jesús Joglar, Marielle Lemaire and Pere Clapés

      Article first published online: 24 JUN 2009 | DOI: 10.1002/anie.200902065

      Thumbnail image of graphical abstract

      New facets of enzyme activity: D-Fructose-6-phosphate aldolase (FSA) catalyzes the self-aldol reaction of glycolaldehyde (GA) and its cross-aldol addition to other aldehydes. As the affinity of GA for FSA as a donor is higher than that as an acceptor, cross-aldol reactions are possible with good to poor aldehyde acceptors if the concentration of GA in the reaction is kept low.

    23. Main-Group Chemistry

      A Short Bi[DOUBLE BOND]Bi Bond Supported by a Metalloid Group 13 Ligand (pages 5526–5529)

      Ganesan Prabusankar, Christian Gemel, Pattiyil Parameswaran, Charity Flener, Gernot Frenking and Roland A. Fischer

      Article first published online: 24 JUN 2009 | DOI: 10.1002/anie.200902172

      Thumbnail image of graphical abstract

      Bismuth goes GaGa: Dibismuthenes are derived from commercially available bismuth(III) triflate or aryloxide salts by employing [Ga(ddp)] (ddp=CH[MeC(2,6-iPr2C6H3)N]2) as an efficient reducing agent and trapping ligand. Apart from the shortest bismuth–bismuth bonds known to date, the compounds demonstrate the unique synthetic potential in main-group chemistry of low-coordinate Group 13 compounds analogous to N-heterocyclic carbenes.

    24. P[BOND]P Activation

      Nonmetal-Mediated Fragmentation of P4: Isolation of P1 and P2 Bis(carbene) Adducts (pages 5530–5533)

      Olivier Back, Glenn Kuchenbeiser, Bruno Donnadieu and Guy Bertrand

      Article first published online: 19 JUN 2009 | DOI: 10.1002/anie.200902344

      Thumbnail image of graphical abstract

      Cutting P4in pieces! Stable singlet carbenes react with white phosphorus at room temperature to afford P4 , P3 , P2 , and even P1 fragments that are stabilized by the carbene moiety (see picture). This process of activation and fragmentation, which was previously carried out using transition metals, can lead to the environmentally friendly production of phosphorus derivatives.

    25. Gold Catalysis

      Gold-Catalyzed Cycloaromatization of 2,4-Dien-6-yne Carboxylic Acids: Synthesis of 2,3-Disubstituted Phenols and Unsymmetrical Bi- and Terphenyls (pages 5534–5537)

      Patricia García-García, Manuel A. Fernández-Rodríguez and Enrique Aguilar

      Article first published online: 8 MAY 2009 | DOI: 10.1002/anie.200901269

      Thumbnail image of graphical abstract

      Round numbers: A gold-catalyzed 2,7-cycloaromatization of captodative dienyne carboxylic acids has been developed that occurs at room temperature with low catalyst loading and total regioselective control (see scheme). The reaction is totally dependent on the electronic properties of the dienyne acid: if a strong electron-donating group is not directly linked to the triple bond, a 1,6-cyclization/decarboxylation sequence takes place.

    26. B[BOND]B Bond Protonation

      Synthesis of a Stable B2H5+ Analogue by Protonation of a Double Base-Stabilized Diborane(4) (pages 5538–5541)

      Oxana Ciobanu, Elisabeth Kaifer, Markus Enders and Hans-Jörg Himmel

      Article first published online: 16 JUN 2009 | DOI: 10.1002/anie.200901842

      Thumbnail image of graphical abstract

      Polarity of H+reversed: The synthesis of [B2H3(hpp)2]+I,a dinuclear borohydride with terminal and bridging H atoms (see picture; B yellow, N blue, C gray, H white, I purple), is made possible with the ligand hexahydropyrimidopyrimidate (hpp). In the course of the reaction the proton is converted into a hydride.

    27. Bio-Electrochemistry

      Imaging Single Enzyme Molecules under In Situ Conditions (pages 5542–5544)

      Claudia Baier and Ulrich Stimming

      Article first published online: 24 JUN 2009 | DOI: 10.1002/anie.200806144

      Thumbnail image of graphical abstract

      A change of image: Single molecules of horseradish peroxidase are investigated by scanning electrochemical potential microscopy (SECPM) and electrochemical STM (EC-STM). SECPM delivers images (left) of single enzymes that are of greater detail than those obtained by EC-STM (right) and even shows an enzyme molecule not visible in the STM image.

    28. Chiral Macrocycles

      An Enantiomerically Pure Alleno-Acetylenic Macrocycle: Synthesis and Rationalization of Its Outstanding Chiroptical Response (pages 5545–5548)

      José Lorenzo Alonso-Gómez, Pablo Rivera-Fuentes, Nobuyuki Harada, Nina Berova and François Diederich

      Article first published online: 16 JUN 2009 | DOI: 10.1002/anie.200901240

      Thumbnail image of graphical abstract

      The unique combination of geometric and electronic properties explains the remarkable magnitude of the Cotton effects in the circular dichroism spectra of new enantiomerically pure alleno-acetylenic macrocycles (see picture). The macrocycles (P,P,P,P)-(−)-1 (red) and (M,M,M,M)-(+)-1 (blue) were prepared in three steps starting from optically pure 1,3-di-tert-butyl-1,3-diethynylallenes.

  11. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. You have free access to this content
      Preview: Angew. Chem. Int. Ed. 31/2009 (page 5553)

      Article first published online: 8 JUL 2009 | DOI: 10.1002/anie.200990158

SEARCH

SEARCH BY CITATION