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Graphical Abstract Angew. Chem. Int. Ed. 202005

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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:
G. Ulrich,* C. Goze, M. Guardigli, A. Roda, R. Ziessel*
Pyrromethene-dialkynyl–Borane Complexes for Energy Transfer
and Protein Labeling
Y. Ding, A. Mathur, M. Chen, J. Erlebacher*
Epitaxial Casting of Nanotubular Mesoporous Platinum
A. Lohr, M. Lysetska, F. Wrthner*
Supramolecular Stereomutation in Kinetic and Thermodynamic
Self-Assembly of Helical Merocyanine Dye Nanorods
P. Raiteri,* R. Martok, M. Parrinello
Exploring Polymorphism: The Case Of Benzene
Y. Tanaka, H. Katagiri, Y. Furusho,* E. Yashima*
A Modular Strategy to Artificial Double Helices by using
Supramolecular Complexation of Crescent-Shaped m-Terphenyl
Derivatives Driven by Amidinium/Carboxylate Salt Bridge
Formation
S. Bonhommeau, G. Molnr, A. Galet, A. Zwick, J.-A. Real,
J. J. McGarvey, A. Bousseksou*
One-Shot-Laser-Pulse-Induced Reversible Spin Transition
in the Spin-Crossover Complex {Fe(C4H4N2)[Pt(CN)4]} at
Room Temperature
Meeting Reviews
Stimulating Chemistry and Strong Bonds
M. Mller
3000
Books
Chasing the Molecule
John Buckingham
reviewed by F. Maaß
3002
RNA Interference in Practice
Ute Schepers
reviewed by N. Polacek
3003
Carbocation Chemistry
George A. Olah, G. K. Surya Prakash
reviewed by D. Lenoir
3003
Highlights
Metal-Metal Interactions
A. Schnepf,* H.-J. Himmel* 3006 – 3008
Subvalent Compounds Featuring Direct
Metal–Metal Bonds: The ZnZn Bond in
[Cp*2Zn2]
Something to zinc about: Subvalent
compounds with direct metal–metal
bonds have been the focus of interest for
many decades. Recently the first synthesis
of a molecular compound with a direct
ZnZn bond was reported. The synthetic
route, although not understood, might
lead the way to other interesting compounds featuring direct metal–metal
bonds, for example, of Group 2 elements.
Minireviews
Olefin Metathesis
T. J. Katz*
3010 – 3019
Olefin Metatheses and Related Reactions
Initiated by Carbene Derivatives of Metals
in Low Oxidation States
2988
Highs and lows: Tungsten carbenes do
not have to be in their highest oxidation
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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state to initiate olefin metatheses,
acetylene polymerizations, and enyne
metatheses. Although low-oxidationstate metal carbenes are less active than
those currently used, the former exhibit
greater stereoselectivity and a broader
substrate range.
Angew. Chem. Int. Ed. 2005, 44, 2988 – 2998
Angewandte
Chemie
Reviews
Carbocycle Synthesis
Goodbye to the weakest link: The intermolecular Pauson–Khand reaction (see
scheme) has in the past been limited by
the poor reactivity and selectivity of the
alkene component. Concerted efforts to
broaden the scope of the intermolecular
Pauson–Khand reaction are critically and
comprehensively covered based on the
reactivity characteristics of the alkene
partners, which are used to rationalize
successful and failed reactions.
S. E. Gibson,* N. Mainolfi
3022 – 3037
The Intermolecular Pauson–Khand
Reaction
Communications
Metallocene Chemistry
C. S. Griffith, G. A. Koutsantonis,*
B. W. Skelton, A. H. White
3038 – 3043
Reaction of Ruthenium Ethyne-1,2-diyl
Compounds with Bis(trimethylsilyl)acetylene Complexes of Titanocene and
Zirconocene: Remarkable Transfer of a C2
Ligand
Carbon ligand transfer: Compound 1 is
formed with reactive metal–ligand fragments generated from Group 4 metallocene compounds. Dropwise addition of
ethanolic HCl to a solution of complex 1 in
toluene affords complex 2 in a carbon–
carbon bond-forming transformation that
is thought to be unprecedented.
Host–Guest Chemistry
V. G. Organo, A. V. Leontiev, V. Sgarlata,
H. V. R. Dias,*
D. M. Rudkevich*
3043 – 3047
Even better than the real thing? As host
molecules, long synthetic nanotubes may
be reasonable alternatives to single-walled
nanotubes. For example, calixarene-based
nanotubes effectively pack into infinite
tubular bundles in the solid state (see
picture), and they can be easily filled with
guest molecules to form stable, but
reversible, encapsulation complexes.
Supramolecular Features of CalixareneBased Synthetic Nanotubes
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Angew. Chem. Int. Ed. 2005, 44, 2988 – 2998
www.angewandte.org
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
2989
Angewandte
Chemie
Formation of the vinylogous bridge
between adjacent pyrrole rings (A and B)
in the reaction of 5,10,15-triphenylcorrole
with CI4 affords the corresponding hemiporphycene (see structure; N blue, I pink,
C white, H green). This approach allows a
facile preparation of functionalized hemiporphycenes.
Corrole Chemistry
Raising the bar. Tethering the macrocyclic
polyether to the tetracationic cyclophane
in a “donor–acceptor” [2]catenane (see
schematic representation) slows down
the process of partial pirouetting of the
crown ether around the cyclophane by a
factor of 10 000. This level of structural
control has important consequences for
the design of the next generation of
molecular switches that depend on bistable “donor–acceptor” [2]catenanes.
Molecular Devices
R. Paolesse,* S. Nardis, M. Stefanelli,
F. R. Fronczek,
M. G. H. Vicente
3047 – 3050
Hemiporphycene from the Expansion of a
Corrole Ring
Y. Liu, P. A. Bonvallet, S. A. Vignon,
S. I. Khan, J. F. Stoddart*
3050 – 3055
Donor–Acceptor Pretzelanes and a
Cyclic Bis[2]catenane Homologue
Asymmetric Catalysis
T. Kano, J. Takai, O. Tokuda,
K. Maruoka*
3055 – 3057
A robust binaphthyl-based amino acid
((S)-1) exhibits higher stability and selectivity than proline for the catalysis of a
direct asymmetric aldol reaction between
aldehydes and acetone (see scheme;
DMF = N,N-dimethylformamide).
Olefinic, heteroaromatic, and aromatic
aldehydes were found to be suitable
substrates, with the corresponding
aldol adducts being obtained in good
yields and excellent enantioselectivities.
Protein–DNA Arrays
Weaving with DNA: A DNA-binding protein was used to control the structure of a
self-assembled 2D crystal. In the absence
of protein, four oligonucleotides hybridize
to form a Kagome lattice of interwoven
double helices with p3 symmetry (see
image). Addition of protein RuvA during
assembly changes the symmetry and
connectivity to give a DNA–protein crystal
with an approximately square unit cell.
Angew. Chem. Int. Ed. 2005, 44, 2988 – 2998
Design of an Axially Chiral Amino Acid
with a Binaphthyl Backbone as an
Organocatalyst for a Direct Asymmetric
Aldol Reaction
J. Malo, J. C. Mitchell, C. Vnien-Bryan,
J. R. Harris, H. Wille, D. J. Sherratt,
A. J. Turberfield*
3057 – 3061
Engineering a 2D Protein–DNA Crystal
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2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
2991
Contents
Molecular Devices
D. A. Leigh,* M. . F. Morales,
E. M. Prez, J. K. Y. Wong, C. G. Saiz,
A. M. Z. Slawin,* A. J. Carmichael,
D. M. Haddleton,* A. M. Brouwer,*
W. J. Buma,* G. W. H. Wurpel, S. Len,
F. Zerbetto*
3062 – 3067
Patterning through Controlled
Submolecular Motion: Rotaxane-Based
Switches and Logic Gates that Function in
Solution and Polymer Films
Shedding light on a mechanical event:
Films of a polymer–rotaxane conjugate
were cast on quartz slides, the films were
covered with aluminum masks, and the
unmasked areas were exposed to vapors
of DMSO. The solvent induces a change
in position of the macrocycle in the
molecular shuttle that leads to “on” states
of the rotaxane fluorescence in the
unmasked areas (see image).
A convergent strategy involving a basemediated silyl transfer/acylation for fragment coupling and a tandem process
consisting of nitro reduction and acyl
transfer can be employed to construct
strained, bicyclic macrolactams (see
scheme). The tetracyclic core of the
tetrapetalones, which are effective lipoxygenase inhibitors, can be prepared by
using an IIII-promoted cyclization.
Natural Product Synthesis
X. Wang, J. A. Porco, Jr.*
3067 – 3071
Synthesis of the Tetracyclic Core of the
Tetrapetalones through Transannular
Oxidative [4þ3] Cyclization
Iron Clusters
B. Godin, Y.-G. Chen, J. Vaissermann,
L. Ruhlmann, M. Verdaguer,
P. Gouzerh*
3072 – 3075
Coordination Chemistry of the
Hexavacant Tungstophosphate
[H2P2W12O48]12 with FeIII Ions:
Towards Original Structures of
Increasing Size and Complexity
Six FeIII centers are incorporated into the
tungstophosphate anion [H2P2W12O48]12
upon reaction with FeCl3. The {P2W12Fe6}
unit thus formed has been characterized
in [H4P2W12Fe9O56(OAc)7]6 and
[H56P8W48Fe28O248]28. The latter is a
supramolecular polyoxotungstate in
which each of the four {P2W12Fe6} units is
connected by three Fe-O-Fe bridges (see
structure). Magnetic studies indicate
strong antiferromagnetic coupling
between the FeIII centers.
Zeolites
Polarized liquid/liquid interfaces can be
used to control ion-exchange processes.
This concept is illustrated with respect to
zeolites, specifically with the replacement
of Na+ with H+ ions in zeolite Y. The
schematic diagram shows the ion
exchange in a zeolite suspended in an
aqueous phase with the selective extraction of Na+ ions into an organic phase.
M. J. Stephenson, S. M. Holmes,
R. A. W. Dryfe*
3075 – 3078
Electrochemically Controlled Ion
Exchange: Proton Exchange with Sodium
Zeolite Y
2992
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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Angew. Chem. Int. Ed. 2005, 44, 2988 – 2998
Angewandte
Chemie
Metamagnetism
Two different types of coordination sheets
made up of CoII ions, 3-hydroxypicolinate,
and 4,4’-bipyridine interpenetrate to form
a unique molecular-based magnetic
material (see picture). This material
displays a low-field metamagnetic
transition and spin-canted behavior.
M.-H. Zeng, W.-X. Zhang, X.-Z. Sun,
X.-M. Chen*
3079 – 3082
Spin Canting and Metamagnetism in a 3D
Homometallic Molecular Material
Constructed by Interpenetration of Two
Kinds of Cobalt(ii)-Coordination-Polymer
Sheets
Key prenucleation species like the openchain tetramer and the four-memberedring structure shown are implicated in the
formation of zeolites according to density
functional theory calculations. The role of
the solvent and the pH value is confirmed
in the control of condensation reactions,
particularly those favoring the formation
of cyclic structures present in many
zeolite structures.
Zeolite Assembly
M. J. Mora-Fonz, C. R. A. Catlow,*
D. W. Lewis*
3082 – 3086
Oligomerization and Cyclization
Processes in the Nucleation of
Microporous Silicas
Organocatalysts
B. Trk,* M. Abid, G. London, J. Esquibel,
M. Trk, S. C. Mhadgut, P. Yan,
G. K. S. Prakash*
3086 – 3089
Readily available cinchona alkaloids have
been used as organocatalysts in the highly
efficient stereoselective hydroxyalkylation
of heteroaromatics such as indoles with
3,3,3-trifluoropyruvate (2, see scheme).
High yields and ee values of both enantiomers of the products, depending on the
catalyst used, indicate the usefulness of
the developed methodology.
Highly Enantioselective Organocatalytic
Hydroxyalkylation of Indoles with
Ethyl Trifluoropyruvate
Biomolecular NMR Spectroscopy
W. Bermel, I. Bertini,* L. Duma, I. C. Felli,
L. Emsley, R. Pierattelli,
P. R. Vasos
3089 – 3092
The detection of 13C is now amenable to
high-resolution NMR spectroscopy of
proteins. A protocol for 13C homonuclear
decoupling in multidimensional experiments correlates carbonyl, Ca, and Cb
Angew. Chem. Int. Ed. 2005, 44, 2988 – 2998
nuclei (see picture). These techniques
also allow the detection of side-chain
nuclei in exclusively heteronuclear experiments, and thus the complete assignment
of proteins.
www.angewandte.org
Complete Assignment of Heteronuclear
Protein Resonances by Protonless NMR
Spectroscopy
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
2993
Contents
Biradical Intermediates
J. Roithov, D. Schrder,*
H. Schwarz
3092 – 3096
Generation of the Elusive
meta-Benzoquinone in the Gas Phase
Ready for matrix isolation? The existence
of meta-benzoquinone has been established unambiguously by a combination
of neutralization–reionization mass spectrometry and computational studies (see
picture). The results suggest that this
elusive member of the family of organic
biradicals should be accessible in matrixisolation experiments.
Synthetic Methods
S. Torssell, M. Kienle,
P. Somfai*
3096 – 3099
1,3-Dipolar Cycloadditions of Carbonyl
Ylides to Aldimines: A Three-Component
Approach to syn-a-Hydroxy-b-amino
Esters
A highly diastereoselective RhII-catalyzed
1,3-dipolar cycloaddition leads to the
formation of syn-b-amino alcohols and
syn-a-hydroxy-b-amino acids in high yields
(see scheme; p-TSA = para-toluenesul-
Semiconductors
U. Jeong, Y. Xia*
fonic acid, Bn = benzyl). This three-component approach to the addition of metalassociated carbonyl ylides to aldimines
was applied to a short enantioselective
synthesis of the C13 side chain of taxol.
Amorphous Se (a-Se) as monodispersed
spherical colloids are used as templates to
synthesize core–shell particles comprising a-Se cores and Ag2Se shells (see
picture). As the temperature is increased,
the particles undergo two phase transitions, the second of which is reversible. By
exploiting the reversibility between the
semiconductive and superionic phases of
the Ag2Se shell, photonic crystals with
thermally switchable stop bands are
made.
3099 – 3103
Photonic Crystals with Thermally
Switchable Stop Bands Fabricated from
Se@Ag2Se Spherical Colloids
Gas Sensors
J.-M. Barbe,* G. Canard, S. Brands,
R. Guilard*
3103 – 3106
Organic–Inorganic Hybrid Sol–Gel
Materials Incorporating Functionalized
Cobalt(iii) Corroles for the Selective
Detection of CO
2994
Selective adsorption of CO over N2 and O2
by the title compounds make these
materials ideal candidates for use in CO
sensors (see picture). The materials are
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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prepared by a sol–gel process and exhibit
greater chemical stability than analogous
isolated cobalt(iii) corrole complexes.
Angew. Chem. Int. Ed. 2005, 44, 2988 – 2998
Angewandte
Chemie
Luminous: The AuIII alkynyl complexes
[Au(C^N^C)(CCR)] [HC^N^CH = 2,6diphenylpyridine, R = C6H5 (1), C6H4-Cl-p
(2), C6H4-OCH3-p (3), C6H4-NH2-p (4);
HC^N^CH = 2,6-bis(4-tert-butylphenyl)pyridine, R = C6H5 (5)] were prepared, and
the molecular structure of 1 was characterized (see picture). Complexes 1–5
display luminescence in solution and in
the solid state both at low and ambient
temperature.
Luminescent Gold Complexes
V. W.-W. Yam,* K. M.-C. Wong, L.-L. Hung,
N. Zhu
3107 – 3110
Luminescent Gold(iii) Alkynyl
Complexes: Synthesis, Structural
Characterization, and Luminescence
Properties
Natural Products Synthesis
J. Yamaguchi, H. Kakeya, T. Uno, M. Shoji,
H. Osada, Y. Hayashi*
3110 – 3115
A biomimetic pathway to lucilactaene (1)
from NG-391 has been developed which
involves stereoselective reactions under
very mild conditions. It was demonstrated
that 1 racemizes rapidly, and the conditions under which racemization occurs
were elucidated. Lucilactaene (1) isolated
under neutral conditions is racemic,
which suggests that either the natural
product is racemized rapidly in the
mycelia, or racemic 1 is biosynthesized.
Determination by Asymmetric Total
Synthesis of the Absolute Configuration of
Lucilactaene, a Cell-Cycle Inhibitor in
p53-Transfected Cancer Cells
Arylation
M. V. Nandakumar,
J. G. Verkade*
A double-amination/intermolecular-Heckreaction sequence is used as a one-pot
methodology for sequential CN and CC
bond formations. 4-Aminostyrene was
coupled with aryl bromides and aryl
iodides using a [Pd2(dba)3]/proazaphos-
phatrane catalyst system (dba = dibenzylideneacetone; see scheme) to form
trans 4-N,N-diaryl aminostilbene derivatives in high yields, which are comparable
to those of previously reported multistep
syntheses.
3115 – 3118
One-Pot Sequential N and C Arylations:
An Efficient Methodology for the
Synthesis of trans 4-N,N-Diaryl
Aminostilbenes
Nucleic Acids
J. Gao, H. Liu, E. T. Kool*
Expanding DNA: The four natural DNA
nucleotides were combined with four
benzo-homologous nucleotides to make
self-assembling double helices (see basepaired structures). Strands of this “xDNA”
Angew. Chem. Int. Ed. 2005, 44, 2988 – 2998
form highly stable, sequence-specific
duplexes with native DNA and RNA, and
can expand the information capacity of
DNA from a basis of four to eight
characters.
www.angewandte.org
3118 – 3122
Assembly of the Complete Eight-Base
Artificial Genetic Helix, xDNA, and Its
Interaction with the Natural Genetic
System
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
2995
Contents
Cluster Compounds
Transition metal oxide cluster anions in
the gas phase have been investigated by
infrared spectroscopy (see picture). In
combination with density functional calculations, the spectra produce compelling
evidence that these anions have polyhedral cage structures. With increasing
size, the extra electron becomes localized,
which leads to a lowering of the symmetry
of the polyhedra from D2d to Cs.
K. R. Asmis,* G. Santambrogio,
M. Brmmer, J. Sauer*
3122 – 3125
Polyhedral Vanadium Oxide Cages:
Infrared Spectra of Cluster Anions and
Size-Induced d Electron Localization
Oxidative Heck Reaction
N. P. Grimster, C. Gauntlett,
C. R. A. Godfrey,
M. J. Gaunt*
3125 – 3129
Palladium-Catalyzed Intermolecular
Alkenylation of Indoles by SolventControlled Regioselective CH
Functionalization
Transition-Metal Complexes
K. J. Nelson, I. D. Giles, W. W. Shum,
A. M. Arif, J. S. Miller*
3129 – 3132
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
Either the C2- or the C3-substituted
product can be obtained with the same
palladium(ii) catalyst in an oxidative
intermolecular alkenylation of indoles. A
variety of conditions can be used for
derivatization at the 3-position; however,
the presence of acetic acid is required for
the C2-selective process (see scheme).
Further elaboration of the products by a
similar CH functionalization process
leads to the bisalkenylated indoles selectively.
Weak-field cyanide: [CrII(CN)5]3 (1) is
formed upon reaction of excess NEt4CN
with CrII2(OAc)4 and has been structurally
characterized. With a stoichiometric
amount of CN, [CrII2 (CN)9]5 was isolated. [CrII(CN)5]3 has an S = 2 ground
state, a high spin state for a homoleptic
metallocyanide, and offers a new building
block to develop molecule-based magnets.
Boron–Magnesium Reagents
O. Baron, P. Knochel*
3133 – 3135
Preparation and Selective Reactions of
Mixed Bimetallic Aromatic and
Heteroaromatic Boron–Magnesium
Reagents
2996
It’s all in the mix: The magnesiation of
iodoaryl and iodoheteroaryl boronic esters
with iPrMgCl·LiCl leads to mixed bimetallic compounds, which react with a
variety of electrophiles to provide highly
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
functionalized boronic esters (see
scheme). Suzuki cross-coupling reactions
of the resulting boronic esters afford
various polyfunctional aromatic and
heteroaromatic compounds.
Angew. Chem. Int. Ed. 2005, 44, 2988 – 2998
Angewandte
Chemie
Organolithium Compounds
The opening or blocking of a coordination
site at the lithium center (for example by
attachment of THF, see picture; left) leads
to diastereodivergent courses in the reactions of a highly diastereomerically enriched alkyl lithium with Me3SnCl. At room
temperature in noncoordinating solvents
the reagent is configurationally stable and
epimerizes in the presence of THF.
C. Strohmann,* B. C. Abele, K. Lehmen,
D. Schildbach
3136 – 3139
A Highly Diastereomerically Enriched,
Silyl-Substituted Alkyl Lithium,
Configurationally Stable at Room
Temperature
Favored entrance for the privileged. Two
inhibitor structures to address the active
site of aspartic proteases have been
developed. They are equipped with a
central hydroxysulfone unit and, alternatively, a pyrrolidine moiety and decorated
with rationally designed side chains. The
hydroxysulfones bind to HIV protease as
expected, whereas the pyrrolidines display
a surprising, previously unreported binding mode.
Structure Determination
E. Specker, J. Bttcher, H. Lilie, A. Heine,
A. Schoop, G. Mller, N. Griebenow,
G. Klebe*
3140 – 3144
An Old Target Revisited: Two New
Privileged Skeletons and an Unexpected
Binding Mode For HIV-Protease
Inhibitors
NMR Spectroscopy
K. Kobzar, H. Kessler,
B. Luy*
NMR in gummi bears: What started as
pure fun could open up interesting applications: stretched gelatin gels as chiral
polymers can be used to distinguish
Angew. Chem. Int. Ed. 2005, 44, 2988 – 2998
3145 – 3147
enantiomeric solutes through their residual dipolar couplings. The method is
demonstrated on a mixture of l- and dalanine (see picture).
Stretched Gelatin Gels as Chiral
Alignment Media for the Discrimination
of Enantiomers by NMR Spectroscopy
Biomimetic light-harvesting antennae are
made available by noncovalent polymerization of semisynthetic zinc chlorins. The
excellent solubility and the prolonged
stability of the zinc chlorin aggregates
enables spectroscopic investigation of
their reversible formation (see picture).
The rod-shaped structure of these aggregates is experimentally confirmed by
atomic force microscopy.
Dyes
www.angewandte.org
V. Huber, M. Katterle, M. Lysetska,
F. Wrthner*
3147 – 3151
Reversible Self-Organization of
Semisynthetic Zinc Chlorins into
Well-Defined Rod Antennae
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
2997
Contents
Service
2998
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Keywords
3152
Authors
3153
Preview
3155
Angew. Chem. Int. Ed. 2005, 44, 2988 – 2998
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