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Graphical Abstract Angew. Chem. Int. Ed. 132005

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Contents
The following Communications have been judged by at least two referees to be “very
important papers” and will be published online at www.angewandte.org soon:
Kendric J. Nelson, Ian D. Giles, William W. Shum, Atta M. Arif,
Joel S. Miller*
The Myth of Cyanide Always Being a Strong Field Ligand:
Synthesis and Structural Characterization of Homoleptic S = 2
Pentacyanochromate(ii), [CrII(CN)5]3, and
Nonacyanodichromate(ii), [CrII2(CN)9]5
Andrew J. Wilson, Mitsutoshi Masuda, Rint P. Sijbesma,*
E. W. Meijer*
Chiral Amplification in the Transcription of Supramolecular
Helicity into a Polymer Backbone
Mark Gandelman, Eric N. Jacobsen*
Highly Enantioselective Catalytic Conjugate Addition of
N Heterocycles to a,b-Unsaturated Ketones and Imides
Sang Hyuk Im, Yun Tack Lee, Benjamin Wiley, Younan Xia*
Large-Scale Synthesis of Silver Nanocubes: The Role of HCl in
Promoting Cube Perfection and Monodispersity
Sridhar Narayan, John Muldoon, M. G. Finn, Valery V. Fokin,
Hartmuth C. Kolb, K. Barry Sharpless*
“On Water”: Unique Reactivity of Organic Compounds in
Aqueous Suspensions
Tetsuro Murahashi, Christopher R. Clough, Joshua S. Figueroa,
Christopher C. Cummins*
A Ligand Comprised of Dinitrogen and
Methyldiphenylphosphine in a Cationic Molybdenum Complex
News
Distinctions for G. Frey
1908
M. Inoue Gives the Merck Banyu
Lecture
1908
K. C. Nicolaou to Head Biopolis
Laboratory
1908
Books
Energetic Materials
Ulrich Teipel
reviewed by M.-J. Crawford, T. M. Klaptke,
J. Welch
1909
Modern Allene Chemistry
Norbert Krause, Stephen K. Hashmi
reviewed by G. Maas
1909
Highlights
Synthetic Methods
D. J. Wallace*
1912 – 1915
Relay Ring-Closing Metathesis—A
Strategy for Achieving Reactivity and
Selectivity in Metathesis Chemistry
How can uncooperative alkenes be rendered more susceptible to metathesis
reactions? The realization that what is
difficult in an intermolecular sense can
become straightforward when transposed
to a kinetically favorable intramolecular
reaction has led to development of relay
ring-closing metathesis (see scheme).
This provides a method for directing
initiation and propagation of previously
unattainable metathesis sequences.
Essays
History of Science
J. A. Labinger,*
S. J. Weininger*
1916 – 1922
Believe it or not: It can sometimes be
difficult to prove an idea is wrong once it
has caught the human imagination. This
situation is demonstrated for the two
temporally separated cases of phlogiston
and cold fusion. Although there are clear
differences between the two cases, they
both illustrate how difficult it can be to
prove the non-existence of a conceived
idea.
Controversy in Chemistry: How Do You
Prove a Negative?—The Cases of
Phlogiston and Cold Fusion
1898
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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Angew. Chem. Int. Ed. 2005, 43, 1898 – 1907
Angewandte
Chemie
Reviews
An ideal couple: The intramolecular combination of Brønsted and Lewis acids (e.g.
acyloxyborane catalyst shown), or of two
Lewis acids, or of two Brønsted acids
could become a particularly useful tool for
the design of asymmetric catalysts with
high reactivity, selectivity, and versatility.
The inherent reactivity of the associated
components is maintained, and the highly
organized structures provide an efficient
asymmetric environment.
Designed Catalysis
H. Yamamoto,*
K. Futatsugi
1924 – 1942
“Designer Acids”: Combined Acid
Catalysis for Asymmetric Synthesis
Communications
Bridged Nucleic Acids
S. Obika, M. Sekiguchi, R. Somjing,
T. Imanishi*
1944 – 1947
Bridge to the right angle: A methylene
bridge between the C3’ and N5’ atoms
restricts the g dihedral angle of an
oligonucleotide P3’!N5’ phosphor-
amidate within the + sc orientation (see
scheme), which improves duplex-forming
ability and accelerates hydrolytic cleavage.
Liquid Crystals
Nucleation by chiral polyimide surfaces
leads to finite enantioselectivity in the
B4 phase of achiral banana mesogen
molecules (see optical micrograph). An
ee value of 10 % was obtained with rubbed
chiral polyimide surfaces. This technique
opens up new possible ways of controlling
chirality in chemical and biological
systems.
For the USA and Canada:
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Angew. Chem. Int. Ed. 2005, 43, 1898 – 1907
Adjustment of the g Dihedral Angle
of an Oligonucleotide P3’!N5’
Phosphoramidate Enhances Its Binding
Affinity towards Complementary Strands
K. Shiromo, D. A. Sahade, T. Oda,
T. Nihira, Y. Takanishi, K. Ishikawa,
H. Takezoe*
1948 – 1951
Finite Enantiomeric Excess Nucleated in
an Achiral Banana Mesogen by Chiral
Alignment Surfaces
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1899
Angewandte
Chemie
Pump up the volume: Poly(N-isopropylacrylamide) gel containing poly(2-(methacryloyloxy)decyl phosphate) surfactant
(NIPA-PMDP gel) shows a rapid reversible volume decrease above its phasetransition temperature. The gel also
undergoes an abrupt volume change on
laser irradiation, which results in expulsion of a stream of water (see pictures).
The gel can be used in fluid control
systems, such as drug delivery.
Polymer–Surfactant Gels
It’s a wind up: Peeling the skin of an apple
into a single helical ribbon gives a sort of
shell that can be wound back around the
apple. Such a shell can be constructed at
the molecular scale using a helix with a
reduced diameter at both ends which
behaves as a capsule and entraps a small
guest such as water (see picture).
Molecular Recognition
Rapid Swelling/Collapsing
Behavior of Thermoresponsive
Poly(N-isopropylacrylamide) Gel
Containing Poly(2-(methacryloyloxy)decyl
phosphate) Surfactant
J. Garric, J.-M. Lger,
I. Huc*
1954 – 1958
Molecular Apple Peels
Porous Materials
Change and change about: Highly porous,
homochiral metal–organic frameworks
(MOFs) undergo reversible single-crystal
to single-crystal and single-crystal to
amorphous to single-crystal structural
transformations when exposed to solvent
vapors or air. These results suggest that
true heterogeneous asymmetric catalysts
can be built from homochiral MOFs.
C.-D. Wu, W. Lin*
1958 – 1961
Highly Porous, Homochiral Metal–
Organic Frameworks: Solvent-ExchangeInduced Single-Crystal to Single-Crystal
Transformations
Host–Guest Systems
Biporous materials: Two distinct large
channels form within a 3D coordination
network. Each channel adsorbs its own
preferred guest from a mixture of two
guests, such as cyclohexane and
naphthalene, to form two independent
columnar arrays of guests in the crystal
(see figure).
Angew. Chem. Int. Ed. 2005, 43, 1898 – 1907
H. Yan,* H. Fujiwara, K. Sasaki,
K. Tsujii*
1951 – 1954
O. Ohmori, M. Kawano,*
M. Fujita*
1962 – 1964
A Two-in-One Crystal: Uptake of Two
Different Guests into Two Distinct
Channels of a Biporous Coordination
Network
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2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1901
Contents
Surface Structures
Self-assembled tapes: Adsorption and
self-assembly of peptides on mica substrates produces tapes, a single molecule
in thickness, with a cross-b-sheet structure (see picture). A variety of surface
morphologies may be produced depending on the preparation procedure. One of
these, a close-packed monolayer of
parallel-aligned tapes, may be of practical
utility as a functionalized protein-like
surface.
C. Whitehouse,* J. Fang, A. Aggeli,
M. Bell, R. Brydson, C. W. G. Fishwick,
J. R. Henderson, C. M. Knobler,
R. W. Owens, N. H. Thomson, D. A. Smith,
N. Boden*
1965 – 1968
Adsorption and Self-Assembly of Peptides
on Mica Substrates
Controlled Fibril Assembly
J. M. Smeenk, M. B. J. Otten, J. Thies,
D. A. Tirrell, H. G. Stunnenberg,
J. C. M. van Hest*
1968 – 1971
Controlled Assembly of Macromolecular
b-Sheet Fibrils
Blocking out aggregation: Triblock
copolymers consisting of a central
b-sheet polypeptide block with the
repeating [(AlaGly)3GluGly]n sequence
and poly(ethylene glycol) (PEG) of
Mn = 750 g mol1 were prepared and the
assembly properties in the solid state
were investigated. Attachment of PEG
prevented the macroscopic aggregation of
the b-sheet polypeptide portion and,
Mixed-Metal Clusters
M. Koutmos,
D. Coucouvanis*
The reactivity of Fe/S and Fe/Mo/S clusters, similar or analogous to those occurring in biological systems, with thiophilic
metal ions is explored. The synthesis of
two heteropolynuclear clusters with different coordination geometries at different sites is reported. The new clusters
contain FeIII, MoV, and CuI centers in
pseudotetrahedral, pseudooctahedral,
and pseudotrigonal coordination environments, respectively (see structure).
1971 – 1974
Metal Clusters as Ligands: Substitution of
Fe ions in Fe/Mo/S Clusters by Thiophilic
CuI Ions To Give Clusters with
[Cu4Mo2Fe2S8]4+ and [Cu5Mo3Fe4S11]6+
Cores
A transparent thin film of titanate nanotubes turns brown under cathodic polarization in water. This electrochromism
arises from the creation of Ti3+ centers by
proton intercalation into the interlayer
separation of nanotubes. The significant
color change of the titanate nanotubes is a
consequence of their layered nanostructure.
Electrochromism
H. Tokudome,
M. Miyauchi*
1974 – 1977
Electrochromism of Titanate-Based
Nanotubes
1902
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
instead, resulted in the formation of welldefined fibrils.
www.angewandte.org
Angew. Chem. Int. Ed. 2005, 43, 1898 – 1907
Angewandte
Chemie
Sensors
A chameleonic, redox-switchable carrier
molecule: A [4,4]ferrocenophane ligand
can selectively recognize Mg2+ ions
through complexation. This ligand can
transport and release Mg2+ ions by application of an external electrochemical
stimulus across a CH2Cl2 liquid
membrane (see picture). Furthermore,
dramatic color changes are seen, which
allow the potential for “naked-eye”
detection.
A. Caballero, V. Lloveras, A. Trraga,
A. Espinosa, M. D. Velasco,
J. Vidal-Gancedo, C. Rovira, K. Wurst,
P. Molina,* J. Veciana*
1977 – 1981
An Electroactive Nitrogen-Rich
[4.4]Ferrocenophane Displaying RedoxSwitchable Behavior: Selective Sensing,
Complexation, and Decomplexation of
Mg2+ ions
Open-mouthed fullerene swallows H2
whole: Direct observation of a H2 molecule that is fully encapsulated by a
derivative of an aza–thia open-cage fullerene (see model) is achieved by synchrotron X-ray diffraction analysis of
single crystals. A 3D electron-density map
obtained by the maximum entropy
method shows a single H2 molecule (red)
floating in the center of a hollow cavity in
the open-cage fullerene molecule (yellow).
Fullerenes
H. Sawa,* Y. Wakabayashi, Y. Murata,
M. Murata, K. Komatsu
1981 – 1983
Floating Single Hydrogen Molecule in an
Open-Cage Fullerene
Enzyme Inhibitors
Like an organic molecule! A chemically
inert ruthenium complex acts as a metallopharmaceutic inhibitor of the protein
kinase GSK-3 by targeting its ATP-binding
site. It is shown to switch on the Wnt
signal transduction pathway inside living
cells and in Xenopus embryos, which
developed a hyperdorsalized phenotype
(see picture, top; bottom: control specimen) on administration of the complex.
D. S. Williams, G. E. Atilla, H. Bregman,
A. Arzoumanian, P. S. Klein,
E. Meggers*
1984 – 1987
Switching on a Signaling Pathway with an
Organoruthenium Complex
Cell Signaling
J. Liu, X. Wu, B. Mitchell, C. Kintner,
S. Ding,* P. G. Schultz*
1987 – 1990
A Small-Molecule Agonist of the Wnt
Signaling Pathway
A new tool for developmental biology: A
screen of combinatorial chemical libraries
identified the 2-amino-4,6-disubstituted
pyrimidine 1 as a dose-dependent agonist
of Wnt signaling. Tadpoles that developed
from embryos treated with 1 had sub-
Angew. Chem. Int. Ed. 2005, 43, 1898 – 1907
stantial head defects (see right-hand
image; left = control). Compound 1
appears to mimic the effects of a Wnt
ligand in a Xenopus model and may be a
useful tool in the study of physiological
processes that involve the Wnt pathway.
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2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1903
Contents
Polymerization
G. A. Metselaar, J. J. L. M. Cornelissen,*
A. E. Rowan,* R. J. M. Nolte 1990 – 1993
Acid-Initiated Stereospecific
Polymerization of Isocyanopeptides
Host–Guest Systems
X. Liu, G. Chu, R. A. Moss,* R. R. Sauers,*
R. Warmuth*
1994 – 1997
Fluorophenoxycarbene inside a
Hemicarcerand: A Bottled Singlet
Carbene
Molecular Magnetism
Y. Yukawa,* G. Arom,* S. Igarashi,
J. Ribas, S. A. Zvyagin,
J. Krzystek
1997 – 2001
[GdNi6] and [LaNi6]: High-Field EPR
Spectroscopy and Magnetic Studies of
Exchange-Coupled Octahedral Clusters
Recognition with a twist: The acid-initiated polymerization of dipeptide-derived
isocyanides (see scheme) is found to be
an exceptionally stereospecific process
that requires a helical template. The
reaction is very sensitive to the acid
concentration. At high acid concentrations, the template is destroyed and a
competing cyclization reaction becomes
predominant.
Long live the carbene: Longevity is granted to fluorophenoxycarbene when it is
generated photochemically from fluorophenoxydiazirine (see picture) inside a
hemicarcerand. This fleeting, and otherwise nonisolable, singlet carbene is the
first electron-deficient species that has
been stabilized by trapping. NOE experiments suggest that the carbene adopts
the intrinsically less stable cis conformation in the confined inner phase.
The competition between ferromagnetic
and antiferromagnetic exchange for Ni–
Gd and Ni–Ni interactions, respectively,
leads to spin frustration and a degenerate
S = 13/2 spin ground state for the symmetric [GdNi6] cluster in (NMe4)[GdNi6(pro)12](ClO4)4 (Hpro = proline; octahedral core shown). The influence of the
Ni–Ni coupling was probed with the
analogous cluster [LaNi6]. In this case the
lanthanide is diamagnetic, and one
observes an S = 0 ground state.
Enzyme Inhibition
B. G. Reddy, Y. D. Vankar*
2001 – 2004
The Synthesis of Hybrids of d-Galactose
with 1-Deoxynojirimycin Analogues as
Glycosidase Inhibitors
1904
Sweet stop: Sugar–azasugar hybrids as
enzyme inhibitors and leads for drug
discovery are presented. Three hybrids 3
of d-galactose with analogues of 1-deoxynojirimycin were prepared from 3,4,6-triO-benzyl-2-nitro-d-galactal (1) by using
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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ring-closing metathesis as a key reaction
(see scheme); Bn = benyzl, Boc = tertbutoxycarbonyl, n = 0,1, R = Ac/Boc,
R1 = H/OAc, R2 = H/OAc, R3 = H/OAc,
R4 = H/OAc.
Angew. Chem. Int. Ed. 2005, 43, 1898 – 1907
Angewandte
Chemie
Metallacycles
M. Fang, N. D. Jones, M. J. Ferguson,
R. McDonald, R. G. Cavell* 2005 – 2008
An unusual synthetic route to the first
example of a six-membered M-N-P-N-P-C
metallacycle (M = metal atom) is reported
which involves a water-induced rearrangement of the methylated Pt-N-P-C-P-N
carbene 1 to the unique Pt-N-P-N-P-C
platinacyclocarbaphosphazene 2. In the
presence of a Lewis acid (LA), 2 converts
into its orthometalated isomer 3 quantitatively. (OTf = CF3SO3).
Water-Induced Rearrangement of a
Platinacyclic Carbene Produces a
Platinacyclic Carbaphosphazene with
an Intraannular PtC Bond in a
PtNPNPC Ring
Organometallic Chemistry
R. Bejot, S. Tisserand, L. M. Reddy,
D. K. Barma, R. Baati, J. R. Falck,*
C. Mioskowski*
2008 – 2011
Reduction of trihalomethylcarbinols 1
with CrCl2 affords good to excellent
yields of (Z)-a-haloenol esters 2 and
(Z)-b-haloenol ethers 3 through acyl or
hydrogen migration, respectively. The
reaction is proposed to proceed through
regio- and stereoselective rearrangement
of a chromium(iii) Fischer carbene.
(R2 = H, alkyl, aryl; X = F, Cl, Br).
A new secondary building unit with edgesharing 3-rings of BO4 and GeO4 tetrahedra (shown in the picture in turquoise and
yellow, respectively) forms the basis of the
framework of SU-16, a borogermanate
with zeolite topology. SU-16 has threedimensional intersecting 12-ring and 8ring channels. In particular the unusual
elliptical 12-ring channels may make this
zeolite structure interesting for shape
selectivity.
Zeolites
Y. Li, X. D. Zou*
2012 – 2015
SU-16: A Three-Dimensional OpenFramework Borogermanate with a Novel
Zeolite Topology
Light at the end of the tunnel: Single-wall
carbon nanotubes—covalently and noncovalently functionalized with positively
and negatively charged groups—associated with porphyrin counterparts are
absorbed onto transparent electrodes
(see scheme) to yield photochemical
devices that exhibit monochromatic
power conversion efficiencies of up to
8.5 %.
Angew. Chem. Int. Ed. 2005, 43, 1898 – 1907
Stereoselective Transformations of
Trihalomethylcarbinols Induced by
Chromous Chloride
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Functional Materials
D. M. Guldi,* G. M. A. Rahman, M. Prato,
N. Jux, S. Qin, W. Ford
2015 – 2018
Single-Wall Carbon Nanotubes as
Integrative Building Blocks for SolarEnergy Conversion
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1905
Contents
Molecular Switches
D. Sud, T. B. Norsten,
N. R. Branda*
2019 – 2021
Photoswitching of Stereoselectivity in
Catalysis Using a Copper Dithienylethene
Complex
Light controls the outcome of a stereoselective reaction. Only in the ring-open
form can the shown chelate copper(i)
complex transfer its chirality to the cyclo-
Ruthenium-Catalyzed Reactions
R. Aoun, J.-L. Renaud, P. H. Dixneuf,
C. Bruneau*
2021 – 2023
Concomitant Monoreduction and
Hydrogenation of Unsaturated Cyclic
Imides to Lactams Catalyzed by
Ruthenium Compounds
One for two: [Ru4H6(p-cymene)4]Cl2 and
[RuCl2(p-cymene)]2, [Ru], are efficient
catalyst precursors for the selective
transformation of cyclic imides into
Polyoxotungstates
A. Bagno,* M. Bonchio
2023 – 2026
Low-valent palladium compounds with Nheterocyclic carbenes (NHCs) formed
from [Pd(NHC)(h2-alkene)2] (see example) are amazingly selective catalysts for
the hydrogenation of several alkynes to
Z alkenes. One such complex, [Pd{1,3(2,6-diethylphenyl)imidazol-2-ylidene}],
has been employed for the selective
(95 %) hydrogenation of 1-phenyl-1-propyne to (Z)-1-phenyl-1-propene.
Palladium Catalysts
J. W. Sprengers, J. Wassenaar,
N. D. Clement, K. J. Cavell,
C. J. Elsevier*
2026 – 2029
Palladium–(N-Heterocyclic Carbene)
Hydrogenation Catalysts
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
saturated lactams (see scheme). The
catalytic systems operate with the same
reagent (H2) to perform two transformations, namely, monoreduction of the carbonyl groups and hydrogenation of C=C
bonds, with the release only of water,
which is the solvent of the reaction.
Smaller than expected: The empirical rule
that edge and corner junctions give rise to
small and large vicinal NMR tungsten–
tungsten coupling constants, respectively,
in polyoxometalates has led to the
assumption that the W-O-W angle is the
sole factor involved. Why then is the
corner 2JWW coupling in g-[SiW10O36]8 (see
picture) so small? Relativistic DFT calculations show why this is indeed expected.
Vicinal Tungsten–Tungsten Coupling
Constants in Polyoxotungstates: DFT
Calculations Challenge an Empirical Rule
1906
propanation of styrene with ethyl diazoacetate. Irradiation with UV light triggers
the ring-closing reaction of the ligand
rendering it ineffective (see scheme).
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Angew. Chem. Int. Ed. 2005, 43, 1898 – 1907
Angewandte
Chemie
Nanostructures
A.-H. Bae, M. Numata, T. Hasegawa, C. Li,
K. Kaneko, K. Sakurai,
S. Shinkai*
2030 – 2033
Forming an orderly line: Au nanoparticles
can be aligned in one dimension by their
incorporation into the helical structure of
a natural polysaccharide, schizophyllan
1D Arrangement of Au Nanoparticles by
the Helical Structure of Schizophyllan: A
Unique Encounter of a Natural Product
with Inorganic Compounds
(s-SPG, see picture). The hydrophobic
inner cavity of the helix hosts the hydrophobic nanoparticles and aligns the
guests along its length ( 200 nm).
The issues for March 2005 appeared online on the following dates:
Issue 9: February 15. · Issue 10: February 22. · Issue 11: March 2. · Issue 12: March 11
Service
Keywords
2034
Authors
2035
Sources
A15
Preview
2037
Corrigenda
*
While referring to Breslow’s work on catalysis by nucleophilic carbenes derived from
thiamine and model systems, the authors inadvertently left out his work on imidazolium
and oxazolium ions.[1] The authors also wish to emphasize that Breslow was the first to
observe catalysis by nucleophilic carbenes of any kind.
In Equation (18), which refers to work by Enders et al., the reference should be [32]. The
references associated with Equation (19) are [32] and [33].
The omissions and errors are regretted by the authors.
N-Heterocyclic Carbenes: Reagents, Not
Just Ligands!
V. Nair,* S. Bindu,
V. Sreekumar
5130–5135
Angew. Chem. Int. Ed. 2004, 43
DOI 10.1002/anie.200301714
[1] R. Breslow, J. Am. Chem. Soc. 1958, 80, 3719.
An error in the references cited in the published article was noticed. The correct citation
for ref. [5i] is provided below. The authors apologize for the oversight.
[5] i) W. H. Binder, M. J. Kunz, C. Kluger, G. Hayn, R. Saf, Macromolecules 2004, 37, 1749;
W. H. Binder, M. J. Kunz, E. Ingolic, J. Polym. Sci. Polym. Chem. Ed. 2004, 42, 162.
Supramolecular AD Diblock Copolymers
X. Yang, F. Hua, K. Yamato,
E. Ruckenstein, B. Gong,* W. Kim,
C. Y. Ryu*
6471–6474
Angew. Chem. Int. Ed. 2004, 43
DOI 10.1002/anie.200460472
Angew. Chem. Int. Ed. 2005, 43, 1898 – 1907
www.angewandte.org
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1907
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