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Graphical Abstract Angew. Chem. Int. Ed. 352004

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The following Communications are available online (in Wiley InterScience). You can find them, as
well as forthcoming Reviews, Highlights, and Essays, at, under Early View.
S.-X. Liu, C. Tanner, A. Neels, S. Dolder,
S. Leutwyler, P. Renaud, P. Bigler,
S. Decurtins*:
Tetrathiafulvalenes Acting as Leaving
Groups: A Route to Bithiazoles
DOI: 10.1002/anie.200460149
Published online: August 12, 2004
M. Murakami,* M. Hasegawa:
Synthesis and Thermal Ring Opening of
DOI: 10.1002/anie.200460144
Published online: August 12, 2004
F. Jiao, P. G. Bruce*:
Two- and Three-Dimensional Mesoporous
Iron Oxides with Microporous Walls
DOI: 10.1002/anie.200460826
Published online: August 12, 2004
Articles judged by the referees or the editor as being either very important or very urgent are immediately edited, proof-read, and electronically
published once the manuscript has arrived in the editorial office in its final form. As long as there is no page number available these articles should
be cited in the following manner:
Author(s), Angew. Chem. Int. Ed., online publication date, DOI.
Meeting Review
A Radical Show
4550 – 4551
E. Lacte
Mass Spectrometry
Analysis and Purification Methods in
Combinatorial Chemistry
Jrgen H. Gross
reviewed by M. Hesse
Bing Yan
reviewed by G. Jung
Recent strategies used in the hunt for new
active compounds employ chemically
modified proteins that are formed by
ligation techniques and then transformed
chemically. The modified proteins
have been successful both as active
compounds and in the search for new
ligands and binding pockets.
Medicinal Chemistry
J. Rademann*
4554 – 4556
Organic Protein Chemistry:
Drug Discovery through the Chemical
Modification of Proteins
Zeolite Nanoslabs?
H. Ramanan, E. Kokkoli,
M. Tsapatsis*
Nanoslabs (1): Investigations of the
mechanism of formation of tetrapropylammonium (TPA)-silicalite-1 by TEM and
atomic force microscopy (AFM) analysis
(see picture) are not consistent with the
existence of “nanoblocks” or “nanoslabs”
previously proposed by J. A. Martens and
4558 – 4561
On the TEM and AFM Evidence of Zeosil
Nanoslabs Present during the Synthesis
of Silicalite-1
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Angew. Chem. Int. Ed. 2004, 43, 4540 – 4548
Zeolite Nanoslabs
Nanoslabs (2): Small square domains of
lighter contrast observed with TEM on
NaCl particles are attributed to tetrapropylammonium-silicalite-1 nanoslabs
carefully extracted from a nanoslab
suspension (see TEM image).
C. E. A. Kirschhock, D. Liang, A. Aerts,
C. A. Aerts, S. P. B. Kremer, P. A. Jacobs,
G. Van Tendeloo,
J. A. Martens*
4562 – 4564
Asymmetric Catalysis
J.-A. Ma, D. Cahard*
4566 – 4583
Towards Perfect Catalytic Asymmetric
Synthesis: Dual Activation of the
Electrophile and the Nucleophile
Twice as good: The design of new catalysts greatly benefits from the concept of
dual activation (see picture) of the electrophile and the nucleophile, which has
been increasingly applied in catalytic
asymmetric syntheses. This Review gives
some examples of spectacular developments in this area; some mechanistic
models are also discussed.
Hypergolic Mixtures
Highly reactive intermediates, such as
that shown, which arise under special
conditions in hypergolic mixtures of
monomethylhydrazine and nitrogen
tetroxide, may trigger uncontrolled
reaction behavior. Car–Parrinello molecular dynamics simulations provide an
insight into the complex reactions on very
short timescales.
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Angew. Chem. Int. Ed. 2004, 43, 4540 – 4548
C. Nonnenberg, I. Frank,*
T. M. KlapCtke
4586 – 4589
Ultrafast Cold Reactions in the Bipropellant Monomethylhydrazine/Nitrogen
Tetroxide: CPMD Simulations
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2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
So similar yet so different: The crystal
structures of six alcohol solvates of the
title compound (see formula) are found to
be very similar at 200 K. In contrast, their
spin-transition behavior and their structural phase transitions are quite different.
Implications of these observations for
crystal engineering are discussed.
Crystal Engineering
M. Hostettler, K. W. TCrnroos,
D. Chernyshov, B. Vangdal,
H.-B. Brgi*
4589 – 4594
Challenges in Engineering Spin Crossover: Structures and Magnetic Properties
of Six Alcohol Solvates of Iron(ii)
Tris(2-picolylamine) Dichloride
Allylic Substitution
G. Lipowsky, N. Miller,
G. Helmchen*
Come together: Successful cooperation of
iridium and copper yielded a new catalyst
system for allylic alkylation. Branched
alkylation products can be obtained
4595 – 4597
rapidly and with high enantioselectivity
from simple linear precursors (see
scheme; cod = cyclooctadiene).
Regio- and Enantioselective IridiumCatalyzed Allylic Alkylation with In Situ
Activated P,C-Chelate Complexes
A ring-size-selective macrolactonization
and the early introduction of the saccharide portions are the main features of a
total synthesis of the 20-membered
macrolide apoptolidin (see formula),
which induces apoptosis in rat glia cells
transformed with oncogenes.
Natural Products Synthesis
H. Wehlan, M. Dauber,
M.-T. Mujica Fernaud, J. Schuppan,
R. Mahrwald, B. Ziemer,
M.-E. Juarez Garcia,
U. Koert*
4597 – 4601
Total Synthesis of Apoptolidin
Versatile building blocks for the
construction of molecular models
for heterogeneous catalysts are readily
available in high yields in the form of
fully metalated silsesquioxane derivatives,
such as dimeric 1, by using alkali-metal
silylamides as deprotonating agents.
V. Lorenz, S. Gießmann, Y. K. Gun’ko,
A. K. Fischer, J. W. Gilje,
F. T. Edelmann*
4603 – 4606
Fully Metalated Silsesquioxanes: Building
Blocks for the Construction of Catalyst
A Sn-nanorod-templated process was
used for the first synthesis of singlecrystalline wurtzite-type ZnS nanotubes.
The as-grown ZnS nanotubes are structurally uniform single crystals and are
partially filled with Sn (see picture). Most
of the tubes are straight with lengths
ranging from several to tens of micrometers, diameters of about 150–250 nm,
and wall thicknesses of about 50–80 nm.
Angew. Chem. Int. Ed. 2004, 43, 4540 – 4548
Catalyst Models
J. Hu,* Y. Bando, J. Zhan,
D. Golberg
4606 – 4609
Sn-Filled Single-Crystalline Wurtzite-Type
ZnS Nanotubes
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
S. Matsumoto, S. Tsutsui, E. Kwon,
K. Sakamoto*
4610 – 4612
Formation of a Stable, Lattice-Framework
Disilene: A Strategy for the Construction
of Bulky Substituents
Bulky protectors: A one-pot reduction of
with potassium graphite yielded a unique
lattice-framework disilene in 47 % yield
(see scheme). The new polycyclic disilene
Combinatorial Synthesis
Exploring the structural diversity of
peptide dendrimers as synthetic protein
models: A 65 536-membered combinatorial peptide-dendrimer library was prepared by split-and-mix techniques on
beads (see picture). The library was
screened and revealed peptide dendrimers that catalyze fluorogenic ester
hydrolysis and peptide dendrimers that
bind to vitamin B12.
A. Clouet, T. Darbre,
J.-L. Reymond*
4612 – 4615
A Combinatorial Approach to Catalytic
Peptide Dendrimers
Noncovalent Interactions
is C2-symmetric and has a long Si Si
double bond (2.26 Q). Its stability is
attributed to the bulky substituents, which
act as protecting groups.
Subnanosecond ion-pair lifetimes have
been observed for the electrostatic
attachment of divalent spin-carrying
counterions to oppositely charged, rodlike
RuII coordination polymers in solution.
Continuous wave (CW) EPR and double
electron-electron resonance (DEER)
spectroscopy show that the spatial
distribution of the divalent counterions
reflects the spatial distribution of charges
on the polyion (see schematic representation).
D. Hinderberger, O. Schmelz, M. Rehahn,
G. Jeschke*
4616 – 4621
Electrostatic Site Attachment of Divalent
Counterions to Rodlike Ruthenium(ii)
Coordination Polymers Characterized by
EPR Spectroscopy
Liquid Crystals
B. Chen, X. B. Zeng, U. Baumeister,
S. Diele, G. Ungar,
C. Tschierske*
4621 – 4625
Liquid Crystals with Complex
The hexagonal-channeled layer phase
(ChLhex ; see picture, right) is one of the
new liquid-crystalline phases formed by
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
the self-organization of the rigid rodlike
alkali-metal carboxylates shown.
Angew. Chem. Int. Ed. 2004, 43, 4540 – 4548
Homogeneous Catalysis
Cationic gold catalyzes the title reaction in
strong acid solvents with SeVI as the
stoichiometric oxidant. At 180 oC and
27 bar of CH4 turnover numbers of about
30 and methanol concentrations of 0.6 m
have been observed with selectivities
> 90%. DFT calculations indicate that
cationic AuI and AuIII are both viable
catalysts that operate by electrophilic C H
activation and oxidative functionalization
(see picture).
C. Jones, D. Taube, V. R. Ziatdinov,
R. A. Periana,* R. J. Nielsen, J. Oxgaard,
W. A. Goddard III
4626 – 4629
Selective Oxidation of Methane to
Methanol Catalyzed, with C H Activation,
by Homogeneous, Cationic Gold
Natural Products Synthesis
A flexible and modular approach was used
in the convergent and highly stereocontrolled synthesis of the antimitotic agent
dictyostatin. This first total synthesis
establishes its full stereochemistry and
should be amenable to producing useful
quantities and designed analogues of this
molecule, whose conformation closely
resembles that of discodermolide (see
overlayed structures).
I. Paterson,* R. Britton, O. Delgado,
A. Meyer, K. G. Poullennec 4629 – 4633
Total Synthesis and Configurational
Assignment of ( )-Dictyostatin,
a Microtubule-Stabilizing Macrolide of
Marine Sponge Origin
Natural Products Synthesis
Will the real dictyostatin please stand up?
There were five finalists as stereostructures for the potent anticancer agent
dictyostatin; ten, if one were to include
enantiomers. A total synthesis of ( )dictyostatin (1) has ended the decade-old
masquerade and identified the winner as a
structure recently proposed by Paterson
and Wright.
Y. Shin, J.-H. Fournier, Y. Fukui,
A. M. Brckner,
D. P. Curran*
4634 – 4637
Total Synthesis of ( )-Dictyostatin:
Confirmation of Relative and Absolute
Signaling dinucleotides: The first singleisomer synthesis of nicotinamide adenine
dinucleotide phosphate (NADP) is
reported. Installation and maintenance
of sensitive phosphate and pyridinium
functionalities were key to success.
Significantly, conversion of NADP
into the important mammalian second
messenger NAADP was achieved. The
graph shows the biological evaluation of
the activity of the release of Ca2+ ions,
which confirms the identity of NAADP.
Angew. Chem. Int. Ed. 2004, 43, 4540 – 4548
Natural Products Synthesis
J. Dowden,* C. Moreau, R. S. Brown,
G. Berridge, A. Galione,
B. V. L. Potter
4637 – 4640
Chemical Synthesis of the Second
Messenger Nicotinic Acid Adenine
Dinucleotide Phosphate by Total
Synthesis of Nicotinamide Adenine
Dinucleotide Phosphate
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
C. D. Papageorgiou, M. A. Cubillo de Dios,
S. V. Ley, M. J. Gaunt*
4641 – 4644
Enantioselective Organocatalytic
Cyclopropanation via Ammonium
Highly functionalized cyclopropanes
can be produced with excellent enantioselectivity through an amine-catalyzed
organocatalytic cyclopropanation process
(see scheme). Catalytically generated
asymmetric ammonium ylides mediate
the reaction, and the cyclopropane
products can be produced as either
enantiomer by using quinine- or
quinidine-derived catalysts.
A “Nod” in the right direction: Aromatic
analogues of the lipooligosaccharidic
nodulation (Nod) factors involved in the
symbiosis of Sinorhizobium meliloti and
legumes are easily assembled from very
simple precursors by combining biotechnological and chemical procedures. Some
of these analogues (see structure) bind
tightly to a specific binding protein and
form a new class of glycolipid mimics.
Glycolipid Mimics
N. Grenouillat, B. Vauzeilles, J.-J. Bono,
E. Samain, J.-M. Beau*
4644 – 4646
Simple Synthesis of Nodulation-Factor
Analogues Exhibiting High Affinity
towards a Specific Binding Protein
Natural Products Synthesis
H. Muratake,*
M. Natsume*
The barrier has finally been lifted to the
synthesis of hetisine-type alkaloids with
the total synthesis of ( )-nominine (1) in
40 steps from 2-bromo-5-methoxyphenethyl iodide. Key steps in the construction
of the architecturally complex polycyclic
structure of this natural product were a
radical cyclization of an enyne and a
palladium-catalyzed intramolecular
a arylation of an aldehyde.
4646 – 4649
Total Synthesis of ( )-Nominine,
a Heptacyclic Hetisine-Type Aconite
Charge-Transfer Complexes
Y. S. Rosokha, S. V. Lindeman,
S. V. Rosokha, J. K. Kochi*
4650 – 4652
Halide Recognition through Diagnostic
“Anion–p” Interactions: Molecular
Complexes of Cl , Br , and I with Olefinic
and Aromatic p Receptors
Intense colorations and new chargetransfer absorption bands are observed
upon addition of a halide (Cl , Br , I ) to
neutral organic p acceptors with electrondeficient olefinic and aromatic centers.
These phenomena results from noncovalent anion–p interactions (shown schematically), which were confirmed by X-ray
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Angew. Chem. Int. Ed. 2004, 43, 4540 – 4548
Medicinal Chemistry
L. Kværnø, T. Ritter, M. Werder, H. Hauser,
E. M. Carreira*
4653 – 4656
Giving cholesterol the brush off: An
intestinal brush border membrane vesicle
assay has been devised for the convenient
in vitro testing of small molecules for
inhibition of cholesterol absorption. The
assay was used to identify new
nonhydrolyzable glycosides as potent
cholesterol-absorption inhibitors and an
oxazolidinone as an effective replacement
of the b-lactam scaffold of ezetimibe (1).
Quantifiable amounts of HOOOH can be
detected by 1H NMR spectroscopic analysis of the thermal reaction of O3 and
HOOH (see scheme). This first experimental report of a link between these
three oxidants suggests that HOOOH
may be involved in oxidation reactions
that span biological, atmospheric, and
environmental systems.
Red light, green light! Emission through
three-photon upconversion processes
An In Vitro Assay for Evaluation of
Small-Molecule Inhibitors of Cholesterol
P. T. Nyffeler, N. A. Boyle, L. Eltepu,
C.-H. Wong, A. Eschenmoser, R. A. Lerner,
P. Wentworth, Jr.*
4656 – 4659
Dihydrogen Trioxide (HOOOH) Is
Generated during the Thermal Reaction
between Hydrogen Peroxide and Ozone
from polymeric organic–lanthanide complexes (lanthanide, Ln = Tb, Eu) was
observed upon excitation of the tripodal
organic ligand at 845 nm. Multiphoton
absorption by the ligand followed by a
transfer of energy to Ln (see picture;
S = singlet state, T = triplet state) gives
rise to characteristic Eu (red) or Tb
(green) emission.
Feeling the heat: Surface-initiated atom
transfer radical polymerization was used
to modify a film of aligned carbon nanotubes with poly(N-isopropylacrylamide)
(see TEM image). A distinct temperature
responsiveness is found for both the
macroscopic (wettability) and the microscopic (the diameter and rigidity of a
single carbon nanotube) properties of the
resulting film.
Surface Chemistry
K.-L. Wong, W.-M. Kwok, W.-T. Wong,*
D. L. Phillips,*
K.-W. Cheah*
4659 – 4662
Green and Red Three-Photon
Upconversion from Polymeric
Lanthanide(iii) Complexes
T. Sun, H. Liu, W. Song, X. Wang, L. Jiang,*
L. Li,* D. Zhu
4663 – 4666
Responsive Aligned Carbon Nanotubes
Communications labeled with this symbol have been judged by two referees as being “very important papers”.
Angew. Chem. Int. Ed. 2004, 43, 4540 – 4548
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Sister Journals
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
4670 – 4671
Angew. Chem. Int. Ed. 2004, 43, 4540 – 4548
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abstract, int, angel, chem, graphical, 352004
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