Chemistry – An Asian Journal

Cover image for Vol. 1 Issue 1‐2

July 17, 2006

Volume 1, Issue 1-2

Pages 3–291

  1. Editorials

    1. Top of page
    2. Editorials
    3. Focus Reviews
    4. Full Papers
    5. Previews
    1. You have free access to this content
      A Quantum Leap (page 3)

      Ryoji Noyori

      Article first published online: 3 JUL 2006 | DOI: 10.1002/asia.200600161

    2. You have free access to this content
      The Premier Journals for Chemistry … (pages 4–5)

      Peter Gölitz and José Oliveira

      Article first published online: 3 JUL 2006 | DOI: 10.1002/asia.200600173

    1. Cover Picture: Polymerization in Coordination Nanospaces (Chem. Asian J. 1-2/2006) (page 6)

      Takashi Uemura, Satoshi Horike and Susumu Kitagawa

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200690001

      Inspired by Nature and the elegant polymerizations that occur in biological systems, chemists are facing up to the challenge of creating materials with well-defined nanostructures. In their Focus Review on page 36 ff., S. Kitagawa and co-workers describe how porous coordination polymers can be prepared with such regular channel structures, whose flexible pores and unique surface potentials allow precisely controlled polymerization and polymer arrangement. The cover picture represents polystyrene in the cavity of [Zn2(1,4-dicarboxylate)2(triethylenediamine)]n. Polymerization of styrene in these nanochannels exhibits living radical nature and thus suggests the possibility of molecular-weight control.

    2. You have free access to this content
      The 0th International Conference on Cutting-Edge Organic Chemistry in Asia—Asian Core Program (ACP) and IUPAC East Asian Networking Project (pages 18–20)

      Minoru Isobe and Pauline Chiu

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600176

      The 0th International Conference on Cutting-Edge Organic Chemistry in Asia—Asian Core Program (ACP) and IUPAC East Asian Networking Project

  2. Focus Reviews

    1. Top of page
    2. Editorials
    3. Focus Reviews
    4. Full Papers
    5. Previews
    1. Multiphase Organic Synthesis in Microchannel Reactors (pages 22–35)

      Juta Kobayashi, Yuichiro Mori and Shū Kobayashi

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600058

      Thumbnail image of graphical abstract

      Channelling efforts: Multiphase organic reactions can be conducted effectively in microchannel reactors. A variety of organic reactions have been optimized for such systems by exploiting different aspects, such as high specific interfacial area, short molecular diffusion distance, high efficiency for heat transfer, and so on. The Focus Review categorizes these multiphase reactions on the basis of the phases involved.

    2. Polymerization in Coordination Nanospaces (pages 36–44)

      Takashi Uemura, Satoshi Horike and Susumu Kitagawa

      Article first published online: 3 JUL 2006 | DOI: 10.1002/asia.200600074

      Thumbnail image of graphical abstract

      Holey vessels: Recent successful research in porous coordination polymers (PCPs) showed that their nanochannels exhibit unique functions characteristic of their regular nanosized networks. A new successful application is utilization of the nanochannels as a polymerization vessel that allows multilevel controls of polymerization and provides well-defined nanostructures, thus permitting the fabrication of new-generation materials.

  3. Full Papers

    1. Top of page
    2. Editorials
    3. Focus Reviews
    4. Full Papers
    5. Previews
    1. Convergent/Divergent Synthesis and Photophysical Studies of Alternating Benzene–Furan Oligoaryls from Substituted Propargylic Dithioacetals (pages 46–55)

      Chih-Ming Chou, Wei-Qiang Chen, Jia-Hong Chen, Cheng-Lan Lin , Jui-Chang Tseng, Chin-Fa Lee and Tien-Yau Luh

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600026

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      Linking rings: Oligomers of different lengths that contain alternate benzene and furan rings can be synthesized through annulation. These compounds are highly fluorescent in the visible region and are electrochemically active.

    2. Ultrafast Electron Diffraction: Structural Dynamics of Molecular Rearrangement in the NO Release from Nitrobenzene (pages 56–63)

      Yonggang He, Andreas Gahlmann, Jonathan S. Feenstra, Sang Tae Park and Ahmed H. Zewail

      Article first published online: 3 JUL 2006 | DOI: 10.1002/asia.200600107

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      NO release: Ultrafast electron diffraction was used to show that the structural dynamics of a classical reaction, NO release, is essential for elucidating the mechanism of rearrangement and dissociation. The nitrobenzene decomposition pathway involves an intramolecular rearrangement to yield NO and the phenoxyl radical, whose structure was found to be quinoid-like.

    3. Facile Synthesis of Oligosaccharide Probes for the Analysis of Protein–Carbohydrate Interactions (pages 64–75)

      Maki Takatani and Yukishige Ito

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600025

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      Sugar factory: Various oligosaccharides can be assembled easily without the need for chromatographic separation of the intermediates. These compounds were fixed on gold-coated sensor chips via thiol linkers (see figure) for evaluation of their affinity to calreticulin.

    4. Countercation Transport Modeled by Porous Spherical Molybdenum Oxide Based Nanocapsules (pages 76–81)

      Dieter Rehder, Erhard T. K. Haupt, Hartmut Bögge and Achim Müller

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600035

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      In and out: Cellular transmembrane transport of Li+, Na+, K+, and Ca2+ ions along ion channels can be modeled by porous spherical nanosized molybdenum oxide based capsules. As shown by 7Li and 23Na NMR spectroscopy, cavity-internal Li+ can be replaced by Ca2+ and, in part, by Na+ and K+. In a complementary experiment, Li+ does not replace internal Na+ ions. The results are relevant to the understanding of lithium-based therapies.

    5. Dynamic Self-Assembly of an M3L6 Molecular Triangle and an M4L8 Tetrahedron from Naked PdII Ions and Bis(3-pyridyl)-Substituted Arenes (pages 82–90)

      Dillip K. Chand, Kumar Biradha, Masaki Kawano, Shigeru Sakamoto, Kentaro Yamaguchi and Makoto Fujita

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600029

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      Molecular shapes: A double-walled triangle and a tetrahedron are formed from pyridine-appended ligands and the naked PdII ion and remain in dynamic equilibrium, which largely depends on the choice of ligand and anion. The crystal structures of the tetrahedral compounds reveal unique framework topology that is quite different from the previously reported coordination tetrahedra.

    6. Preparation of Nearly Monodisperse Nanoscale Inorganic Pigments (pages 91–94)

      Dingsheng Wang, Xin Liang and Yadong Li

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600078

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      The dye is cast: Several important commercial pigments have been synthesized on the basis of the liquid–solid–solution (LSS) phase-transfer and separation process. They can be well-dispersed in cyclohexane and remain non-agglomerated, even over several months. These nearly monodisperse nanoscale inorganic pigments could potentially have important applications in the pigment industry.

    7. Unexpected Chiroptical Inversion Observed for Supramolecular Complexes Formed between an Achiral Polythiophene and ATP (pages 95–101)

      Chun Li , Munenori Numata, Masayuki Takeuchi and Seiji Shinkai 

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600039

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      Mirrored rarity: Optically active supramolecular complexes were constructed by noncovalent complexation of an achiral water-soluble polythiophene (PT-1) with adenosine triphosphate (ATP) in aqueous medium. The chiroptical inversion of these supramolecular complexes can be achieved by adjusting the ATP concentration (see figure; — (red) [ATP]=0.025 mM, — [ATP]=0.25 mM).

    8. Mechanism of Asymmetric Hydrogenation of Acetophenone Catalyzed by Chiral η6-Arene–N-Tosylethylenediamine–Ruthenium(II) Complexes (pages 102–110)

      Christian A. Sandoval, Takeshi Ohkuma, Noriyuki Utsumi, Kunihiko Tsutsumi, Kunihiko Murata and Ryoji Noyori

      Article first published online: 3 JUL 2006 | DOI: 10.1002/asia.200600098

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      Acid test: Asymmetric hydrogenation of acetophenone (1) in the presence of catalyst 2 in methanol under acidic conditions affords (S)-1-phenylethanol (3) with 96 % ee in 100 % yield. Like the transfer hydrogenation catalyzed by similar Ru catalysts with basic 2-propanol or a formic acid/triethylamine mixture, this hydrogenation with H2 gas proceeds through a metal–ligand bifunctional mechanism. Tf = trifluoromethanesulfonyl, Ts = p-toluenesulfonyl.

    9. Total Synthesis of (±)-Pallavicinin and (±)-Neopallavicinin (pages 111–120)

      Xiao-Shui Peng and Henry N. C. Wong

      Article first published online: 3 JUL 2006 | DOI: 10.1002/asia.200600061

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      Emulating nature: (±)-Pallavicinin and (±)-neopallavicinin were for the first time synthesized from (±)-Wieland–Miescher ketone. The synthetic strategy involves biomimetic Grob fragmentation, intramolecular aldol condensation, and Michael addition. This approach should provide opportunities for access to other related bioactive diterpenoids.

    10. Chiral Scandium Catalysts for Enantioselective Michael Reactions of β-Ketoesters (pages 121–124)

      Chikako Ogawa, Keiko Kizu, Haruka Shimizu, Masahiko Takeuchi and Shu Kobayashi

      Article first published online: 3 JUL 2006 | DOI: 10.1002/asia.200600093

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      Less is more: Michael reactions of β-ketoesters (e.g. 1) with α,β-unsaturated ketones (e.g. 2) proceed highly enantioselectively in the presence of Sc(OTf)3 and a chiral bipyridine 3. The reactions proceeded smoothly in dichloroethane at 40 °C to afford the corresponding Michael adducts 4 in good to high yields with excellent enantioselectivities. The reaction proceeds best at low concentrations. Tf = trifluoromethanesulfonyl.

      Corrected by:

      Corrigendum: Chiral Scandium Catalysts for Enantioselective Michael Reactions of β-Ketoesters

      Vol. 1, Issue 4, 504, Article first published online: 11 OCT 2006

    11. An Efficient Total Synthesis of Optically Active Tetrodotoxin from Levoglucosenone (pages 125–135)

      Daisuke Urabe, Toshio Nishikawa  and Minoru Isobe

      Article first published online: 3 JUL 2006 | DOI: 10.1002/asia.200600038

      Thumbnail image of graphical abstract

      The sweetest poison: Tetrodotoxin (3), a toxic principal of puffer-fish poisoning, was prepared in 22 steps from intermediate 2, which is readily available from levoglucosenone (1). This synthesis is much more efficient than previous asymmetric total syntheses and allows the preparation of a variety of molecular probes of tetrodotoxin for biochemical research.

    12. Flavin-Catalyzed Oxidation of Amines and Sulfides with Molecular Oxygen: Biomimetic Green Oxidation (pages 136–147)

      Yasushi Imada, Hiroki Iida, Satoshi Ono, Yoshiyuki Masui and Shun-Ichi Murahashi 

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600080

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      Imitating nature: A flavin-catalyzed biomimetic, aerobic oxidation simulates the function of flavin monooxygenase. This organocatalytic oxidation of sulfides and secondary and tertiary amines with oxygen or even air in the presence of hydrazine monohydrate at room temperature gives the corresponding products in excellent yields and selectivities along with the environmentally benign by-products water and molecular nitrogen.

    13. New Donor–Acceptor Materials Based on Random Polynorbornenes Bearing Pendant Phthalocyanine and Fullerene Units (pages 148–154)

      Andrés de la Escosura, M. Victoria Martínez-Díaz, Tomás Torres, Robert H. Grubbs, Dirk M. Guldi, Helmut Neugebauer, Christoph Winder, Martin Drees  and N. Serdar Sariciftci

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600090

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      Catching sunlight: The incorporation of both phthalocyanine (Pc) and fullerene (C60) pendant units within polymeric frameworks such as poly(norbornene)s leads to long-lived photoinduced charge-separated states. These copolymers can harvest photons with wavelengths up to the infrared region, therefore making the material an interesting candidate for low-bandgap photovoltaic devices.

    14. New Synthetic Routes to C-Amino Phosphorus Ylides and their Subsequent Fragmentation into Carbenes and Phosphines (pages 155–160)

      Salvador Conejero, Maoying Song, David Martin, Yves Canac, Michele Soleilhavoup and Guy Bertrand

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600075

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      Readily available phosphonio-substituted iminium salts and C-amino phosphaalkenes can be transformed in one step into C-amino phosphorus ylides, which undergo fragmentation into phosphines and amino carbenes. This novel route to amino carbenes promises to be broadly applicable and highly functional-group tolerant.

    15. Nucleophilic Activation of Alkenyl and Aryl Boronates by a Chiral CuIF Complex: Catalytic Enantioselective Alkenylation and Arylation of Aldehydes (pages 161–166)

      Daisuke Tomita, Motomu Kanai and Masakatsu Shibasaki

      Article first published online: 3 JUL 2006 | DOI: 10.1002/asia.200600068

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      Cu/B combo: A new method for catalytic enantioselective alkenylation and arylation of aldehydes involves the activation of alkenyl and aryl boronates by a catalytic amount of a CuIF–DTBM-segphos complex through transmetalation. The resulting novel alkenyl and aryl copper species react with aldehydes to produce optically active secondary allylic alcohols and diaryl methanols with excellent enantioselectivity. Pin=pinacol.

    16. Gene Delivery by Aminofullerenes: Structural Requirements for Efficient Transfection (pages 167–175)

      Hiroyuki Isobe, Waka Nakanishi, Naoki Tomita, Shigeki Jinno, Hiroto Okayama and Eiichi Nakamura

      Article first published online: 4 JUL 2006 | DOI: 10.1002/asia.200600051

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      It takes balls! Screening of over twenty aminofullerenes revealed the structural requirements for these molecules to be efficient gene-delivery reagents. The tetrapiperidinofullerene shown exhibited the highest transfection efficiency.

    17. Mono- and Di(dimethylamino)styryl-Substituted Borondipyrromethene and Borondiindomethene Dyes with Intense Near-Infrared Fluorescence (pages 176–187)

      Yan-Hong Yu, Ana B. Descalzo, Zhen Shen, Holger Röhr, Quan Liu, Yan-Wei Wang, Monika Spieles, Yi-Zhi Li, Knut Rurack and Xiao-Zeng You

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600042

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      To dye for: Bright red or bright near-infrared (NIR) fluorescence emission are the key features of a series of functional borondipyrromethene and borondiindomethene dyes that carry one or two (dimethylamino)styryl units as an extension of the chromophore. The choice of a suitable meso substituent yields pH indicators or metal-ion-responsive dyes with a variety of powerful signaling pathways.

    18. A Femtosecond Study of Excitation-Wavelength Dependence of Solvation Dynamics in a Vesicle (pages 188–194)

      Pratik Sen, Subhadip Ghosh, Sudip Kumar Mondal, Kalyanasis Sahu, Durba Roy, Kankan Bhattacharyya and Keisuke Tominaga

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600036

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      Can you tell the difference? Femtosecond fluorescence upconversion studies of coumarin 480 in a lipid vesicle show two distinct locations with very different solvation times. These sites can be distinguished because of the dependence of the solvation dynamics on excitation wavelength.

    19. Complex of Silylene with Nitrogen: A Combined Matrix-Spectroscopic and Density Functional Theory Study (pages 195–202)

      Günther Maier, Hans Peter Reisenauer, Jörg Glatthaar and Roland Zetzmann

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600089

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      Does siladiazomethane exist? No! Experiment and theory show that the most stable SiH2N2 species is an end-on complex of silylene with nitrogen. Such silylene complexes with carbon monoxide are, however, more stable.

    20. Highly Efficient Three-Component Synthesis of β-Lactams from N-methylhydroxylamine, Aldehydes, and Phenylacetylene (pages 203–209)

      Liang Zhao and Chao-Jun Li

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600097

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      Mix and match: The three-component reaction of N-substituted hydroxylamines, aldehydes, and phenylacetylene catalyzed by CuCl/2,2′-bipyridine in the presence of NaOAc under neat conditions afford the corresponding β-lactams in good to excellent yields (see scheme). The method, which tolerates aromatic, heteroaromatic, and aliphatic aldehydes, allows efficient access to various N-alkyl β-lactam derivatives.

    21. Design of a Binaphthyl-Based Axially Chiral Amino Acid as an Organocatalyst for Direct Asymmetric Aldol Reactions (pages 210–215)

      Taichi Kano, Osamu Tokuda, Jun Takai and Keiji Maruoka

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600077

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      A novel and robust binaphthyl-based amino acid (S)-1 was designed for the direct asymmetric aldol reaction and exhibits higher chemical stability and selectivity than the well-known proline catalyst. The direct asymmetric aldol reaction of a range of ketones and aldehydes afforded the aldol adduct in high yields with high enantioselectivities (e.g. see scheme).

    22. Diffusion-Influenced Reversible Trapping Problem in the Presence of an External Field (pages 216–223)

      Soohyung Park and Kook Joe Shin

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600076

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      New results for an old problem: The effect of an external field on the dynamics of diffusion-influenced processes for irreversible trapping in one dimension has now been extended to reversible traps. These results can be applied to the investigation of the dynamics of electron transfer in semiconductors.

    23. Pyrene-Based Dual-Mode Fluorescence Switches and Logic Gates That Function in Solution and Film (pages 224–230)

      Weidong Zhou, Yongjun Li, Yuliang Li, Huibiao Liu, Shu Wang, Cuihong Li, Mingjian Yuan, Xiaofeng Liu and Daoben Zhu

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600037

      Thumbnail image of graphical abstract

      A logical switch: A particularly simple hingelike molecular switch (see formula) exhibits dual fluorescence responses driven by acid or Zn2+ ions which alternate the excimer/monomer emission ratio of the pyrene units. On the basis of these reversible fluorescence switches, the corresponding integrated logic gates and communication networks have been also constructed.

    24. Packing Modes in Some Mono- and Disubstituted Phenylpropiolic Acids: Repeated Occurrence of the Rare syn,anti Catemer (pages 231–244)

      Dinabandhu Das and Gautam R. Desiraju

      Article first published online: 3 JUL 2006 | DOI: 10.1002/asia.200600046

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      Unusual chains: Although the dimer is almost invariably the default packing mode in carboxylic acids, the syn,anti catemer is preferentially formed in phenylpropiolic acids. Supportive C[BOND]H⋅⋅⋅O hydrogen-bonding interactions are crucial to the adoption of this rare conformation.

    25. Second-Generation Total Synthesis of Azaspiracids-1, -2, and -3 (pages 245–263)

      K. C. Nicolaou, Michael O. Frederick, Eriketi Z. Loizidou, Goran Petrovic, Kevin P. Cole, Theocharis V. Koftis and Yoichi M. A. Yamada

      Article first published online: 4 JUL 2006 | DOI: 10.1002/asia.200600059

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      What′s your poison? The azaspiracids-1 (1), -2 (2), and -3 (3) are naturally occurring marine neurotoxins, whose structures were originally assigned incorrectly. The correct structure of 1 was later confirmed by total synthesis. The second-generation syntheses have confirmed the structures of 2 and 3, and the improved access to these scarce compounds render 13 readily available for biological studies.

    26. Methylation of [Pt2(μ-SR)(μ-S)(PPh3)4]: En Route to Mixed-Thiolato Bridged Complexes (pages 264–272)

      Siew Huay Chong, Lip Lin Koh, William Henderson and T. S. Andy Hor

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200600060

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      Bridging the divide: Conversion of [Pt2(μ-S)2(PPh3)4] into {Pt2(μ-SR)(μ-SCH3)} species such as 1 via {Pt2(μ-SR)(μ-S)} (R=benzyl, allyl, ester, nitrile, dioxolane) gives a series of asymmetric dithiolate-bridged diplatinum complexes. When R carries a suitable pendant donor such as CnSPh, intramolecular phosphine displacement can give a sulfur-rich diplatinum product 2. • (purple) Pt, • (pink) P, • (yellow) S, ○ C (Ph of PPh3 and H atoms not shown).

    27. Luminescent Molecular Copper(I) Alkynyl Open Cubes: Synthesis, Structural Characterization, Electronic Structure, Photophysics, and Photochemistry (pages 273–286)

      Chui-Ling Chan, Kai-Leung Cheung, Wai Han Lam, Eddie Chung-Chin Cheng, Nianyong Zhu, Sam Wing-Kin Choi and Vivian Wing-Wah Yam

      Article first published online: 3 JUL 2006 | DOI: 10.1002/asia.200600067

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      A class of their own: A novel series of tetranuclear CuI–alkynyl complexes with an “open-cube” structure was synthesized ([Cu4{P(p-MeC6H4)3}43112-C≡C-p-MeOC6H4)3]PF6 shown). Their excited-state properties were probed by systematic studies of their electronic absorption and photoluminescence, with DFT calculations, as well as through oxidative quenching experiments and transient absorption spectroscopy.

  4. Previews

    1. Top of page
    2. Editorials
    3. Focus Reviews
    4. Full Papers
    5. Previews
    1. You have free access to this content
      Preview: Chem. Asian J. 3/2006 (page 291)

      Article first published online: 10 JUL 2006 | DOI: 10.1002/asia.200690000

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