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Graphical Abstract Angew. Chem. Int. Ed. 72004

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Contents
The following articles are available online (in Wiley InterScience). You can find them at
www.angewandte.org, under Full Text, Early View.
F. F. Kneisel, M. Dochnahl, P. Knochel*:
Nucleophilic Catalysis of the Iodine–Zinc Exchange Reaction:
Preparation of Highly Functionalized Diaryl Zinc Compounds
DOI: 10.1002/anie.200353316
Published online: January 27, 2004
D. Liu, S. Choi, B. Chen, R. J. Doerksen, D. J. Clements, J. D. Winkler,
M. L. Klein, W. F. DeGrado*:
Nontoxic Membrane-Active Antimicrobial Arylamide Oligomers
DOI: 10.1002/anie.200352791
Published online: January 27, 2004
C. L. M. Pereira, E. F. Pedroso, H. O. Stumpf,* M. A. Novak,
L. Ricard, R. Ruiz-Garc-a, E. Rivi.re, Y. Journaux*:
A CuIICoII Metallacyclophane-Based Metamagnet with a
Corrugated Brick Wall Sheet Architecture
DOI: 10.1002/anie.200352604
Published online: January 27, 2004
L. J. Gooßen,* J. Paetzold:
Decarbonylative Heck Olefination of Enol Esters: Salt-Free and
Environmentally Friendly Access to Vinyl Arenes
DOI: 10.1002/anie.200352357
Published online: January 29, 2004
H. Chun, D. Kim, D. N. Dybtsev, K. Kim*:
Metal–Organic Replica of Fluorite Built with an Eight-Connecting
Tetranuclear Cadmium Cluster and a Tetrahedral FourConnecting Ligand
DOI: 10.1002/anie.200353139
Published online: January 27, 2004
L. Hogg, D. A. Leigh,* P. J. Lusby, A. Morelli, S. Parsons,
J. K. Y. Wong:
A Simple General Ligand System for Assembling Octahedral
Metal–Rotaxane Complexes
DOI: 10.1002/anie.200353186
Published online: January 27, 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 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.
News
Organic Chemistry: Distinction to
C. Djerassi
776
Organic Chemistry: T. Bach receives
Novartis Award
776
Bioorganic Chemistry: D. Seebach and
S. Kent recognized
776
The Chemistry of Phenols
778
Zvi Rappoport
reviewed by S. R. Waldvogel
Modern Methods of Drug Discovery
779
Alexander Hillisch, Rolf Hilgenfeld
reviewed by N. Heinrich
Organolithiums in Enantioselective
Synthesis
David M. Hodgson
reviewed by B. Goldfuss
780
Books
Highlights
Structure Determination
B. Simon, M. Sattler*
A useful acquisition: Reducing the
dimensionality of multidimensional NMR
experiments dramatically decreases
measurement times. Where signal-tonoise is not limiting, GFT NMR spectroscopy (see picture) provides a general
scheme for fast data acquisition which
can speed up NMR-based protein-structure determination.
782 – 786
Speeding Up Biomolecular NMR
Spectroscopy
768
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Angew. Chem. Int. Ed. 2004, 43, 768 – 774
Angewandte
Chemie
Reviews
Industrial Chemistry
M. Breuer, K. Ditrich, T. Habicher,
B. Hauer,* M. Keßeler, R. StBrmer,
T. Zelinski
788 – 824
Of fundamental importance for the
pharmaceutical industry is the large-scale
availability of enantiomerically pure intermediates, such as amino acids, amino
alcohols, amines, alcohols, and epoxides.
Industrial Methods for the Production of
Optically Active Intermediates
In this Review industrially relevant syntheses of such intermediates are presented, based on chemical as well as
enzymatic and fermentation processes
(see scheme).
Communications
Site-selective glycosylation by SeSmediated ligation has led to the efficient
formation of a wide variety of conjugates 1
without the need for a large excess of the
carbohydrate reagent. By this convergent
method it was possible to introduce a
heptasaccharide glycan selectively, and to
perform a multiple site-selective chemical
glycosylation of protein. A chemically Cysglycosylated glycoprotein was elaborated
enzymatically.
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Angew. Chem. Int. Ed. 2004, 43, 768 – 774
Glycoproteins
D. P. Gamblin, P. Garnier, S. van Kasteren,
N. J. Oldham, A. J. Fairbanks,
B. G. Davis*
828 – 833
Glyco-SeS: Selenenylsulfide-Mediated
Protein Glycoconjugation—A New Strategy in Post-Translational Modification
Insight into the electronic structures of
high-valent intermediates with the
{FeIV2(m-O)2} “diamond core” is provided
by density theory calculations. These
electronic structures are contrasted with
nitrido-bridged heme dimers that contain
metal centers with the same oxidation
state. Such diamond-core intermediates
might actually occur in the catalytic cycles
of diiron alkane monooxygenases such as
AlkB.
Density Functional Calculations
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www.angewandte.org
A. Ghosh,* E. Tangen, E. Gonzalez,
L. Que, Jr.*
834 – 838
Models of High-Valent Intermediates
of Non-Heme Diiron Alkane Monooxygenases: Electronic Structure of a
Bis(m-oxo)diron(iv) Complex with
Locally Low-Spin Metal Centers
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
769
Contents
Remarkably stable C60 and C70 complexes
with stability constants Ks of
70 680 2060 and 136 620 3770 m1,
respectively, are formed by azacalix[4]arene[4]pyridine 1. The smaller-ring-homologue azacalix[2]arene[2]pyridine and
compound 1 were readily synthesized,
and they adopt a heavily twisted 1,3alternate and a 1,2,3-partial cone conformation, respectively, in the solid state
(see picture).
Fullerene/Azacalixarene Complexes
M.-X. Wang,* X.-H. Zhang,
Q.-Y. Zheng
838 – 842
Synthesis, Structure, and [60]Fullerene
Complexation Properties of Azacalix[m]arene[n]pyridines
Protein–Ligand Interactions
Single-molecule study on multivalency:
The binding kinetics of a tetravalent lectin
can be examined at the single-molecule
level by using an engineered protein pore
carrying up to seven carbohydrate ligands.
The binding of the lectin to the pore (see
molecular model) produces short and
long reversible blockades in single-channel current recordings, which are interpreted as monovalent and bivalent binding events, respectively.
S. Howorka,* J. Nam, H. Bayley,
D. Kahne
842 – 846
Stochastic Detection of Monovalent and
Bivalent Protein–Ligand Interactions
Enantioselective Allylation
G. Zanoni,* S. Gladiali, A. Marchetti,
P. Piccinini, I. Tredici,
G. Vidari
846 – 849
Enantioselective Catalytic Allylation of
Carbonyl Groups by Umpolung of
p-Allyl Palladium Complexes
Diethylzinc mediates the asymmetric
allylation of aldehydes through Umpolung
of a p-allyl palladium complex. An investigation of the palladium source and the
chiral monophosphane ligands have
shown that the leaving group has a
dramatic effect on the enantioselectivity of
the reaction. The procedure furnished
products in satisfactory yields and up to
70 % ee (see scheme).
A hexakis-bidentate building block: Tricopper(ii) and enneacopper(ii) 1,3,5metallacyclophanes were synthesized by a
combination of self-assembly and a
rational approach (see scheme). Both
complexes exhibit ferromagnetic coupling
in the core, through a spin-polarization
mechanism.
Metallacyclophanes
X. Ottenwaelder, J. Cano, Y. Journaux,*
E. RiviSre, C. Brennan, M. Nierlich,
R. Ruiz-GarcTa
850 – 852
Rational Design of an Enneanuclear
Copper(ii) Complex with a Metallacyclophane Core
770
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Angew. Chem. Int. Ed. 2004, 43, 768 – 774
Angewandte
Chemie
Intramolecular Electron Transfer
K. Ohkubo, H. Kotani, J. Shao, Z. Ou,
K. M. Kadish,* G. Li, R. K. Pandey,*
M. Fujitsuka, O. Ito,* H. Imahori,*
S. Fukuzumi*
853 – 856
Long live the state! Photoexcitation of a
zinc chlorin–fullerene dyad with a short
linkage results in the formation of the
ultra-long-lived charge-separated (CS)
state by a one-step photoinduced electron
transfer without loss of energy, which is
inevitable for charge separation by multistep electron-transfer processes. The lifetime of the charge-separated state was
120 s in frozen PhCN at 150 8C (see
picture).
Good for winter: The structure–activity
relationships of antifreeze glycoproteins
(AFGPs) have been characterized by
chemical synthesis and conformational
analysis. The results revealed that the
mode of glycosylation on the threonyl
residue in the tripeptide unit is of primary
importance in the formation of the specific structure for the antifreeze activity
(see picture for the structural requirements of AFGPs).
Glycoproteins
Y. Tachibana, G. L. Fletcher, N. Fujitani,
S. Tsuda, K. Monde,
S.-I. Nishimura*
856 – 862
Antifreeze Glycoproteins: Elucidation of
the Structural Motifs That Are Essential
for Antifreeze Activity
Active-Site Inhibitors
Shaping up for inhibition: Identification of
three-dimensional structural similarities
(see picture) between the active sites of
zinc dinuclear aminopeptidases and trinuclear phospholipase C hydrolytic
enzymes that are not related by sequence
or tertiary structure led to the discovery of
phospholipase C inhibition by a-aminohydroxamic acids, a typical family of
aminopeptidase inhibitors.
Angew. Chem. Int. Ed. 2004, 43, 768 – 774
Production of an Ultra-Long-Lived ChargeSeparated State in a Zinc Chlorin–C60
Dyad by One-Step Photoinduced Electron
Transfer
A. GonzVlez-Roura, I. Navarro, A. Delgado,
A. Llebaria,* J. Casas
862 – 865
Disclosing New Inhibitors by Finding
Similarities in Three-Dimensional ActiveSite Architectures of Polynuclear Zinc
Phospholipases and Aminopeptidases
www.angewandte.org
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
771
Contents
Marine Alkaloid Synthesis
P. Ploypradith, C. Mahidol,
P. Sahakitpichan, S. Wongbundit,
S. Ruchirawat*
866 – 868
A Highly Efficient Synthesis of
Lamellarins K and L by the
Michael Addition/Ring-Closure Reaction
of Benzyldihydroisoquinoline Derivatives
with Ethoxycarbonyl-b-nitrostyrenes
Alkaloid achievement: Lamellarins, a new
class of potential nontoxic inhibitors of
HIV-1 integrase that are also responsible
for multidrug-resistance reversal in cancer
cell lines, could be synthesized in three
chemical steps and in 60 % overall yields
from two simple starting materials (see
scheme). The key step in the convergent
synthetic approach involved the novel
Michael addition/ring-closure reaction to
give the pyrrole core and the ester group
required for subsequent lactonization in
one step.
Remote control: Substituents strongly
affect the catalytic properties of complexes 1 in ethylene polymerization,
despite their remoteness from the active
center. An appropriate substitution pattern provides very active and robust
catalysts.
Polymerization Catalysis
M. A. Zuideveld, P. Wehrmann, C. RWhr,
S. Mecking*
869 – 873
Remote Substituents Controlling Catalytic
Polymerization by Very Active and Robust
Neutral Nickel(ii) Complexes
Organoarsenic Compounds
A. Chrostowska,* A. Dargelos, V. Lemierre,
J.-M. Sotiropoulos, P. Guenot,
J.-C. Guillemin*
873 – 875
First Synthesis and Characterization by
Mass Spectrometry and UV-Photoelectron
Spectroscopy of Methylenearsane
In a vacuum gas–solid reaction (VGSR;
see scheme), the kinetically unstable
methylenearsane was synthesized by
dehydrohalogenation of gaseous chloromethylarsane on solid sodium carbonate
and characterized in the gas phase by
mass spectrometry and UV photoelectron
Confused Porphyrins
A. Srinivasan, T. Ishizuka,
H. Furuta*
Inverted and fused: Meso-pentafluorophenyl-substituted N-confused, doubly Nfused pentaphyrin (see X-ray crystal
structure; green: F, blue: N) was synthesized from [3þ2] coupling of confused
tripyrrane and dipyrromethane dicarbinol,
followed by oxidation. Inverted pyrrole
rings in pentaphyrin are easily transformed into N-fused tripentacyclic rings.
876 – 879
Doubly N-Fused Pentaphyrin
772
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
spectroscopy. A new approach to theoretically evaluate ionization potentials is also
demonstrated.
www.angewandte.org
Angew. Chem. Int. Ed. 2004, 43, 768 – 774
Angewandte
Chemie
Organofluorine Compounds
X. Liu, M. Shimizu,*
T. Hiyama
The stereoselective preparation and Pdcatalyzed cross-coupling reaction of boronates 2 provides a new general and
convenient route to CF3-substituted triaryl
ethenes 3, in which the CF3 and Ar3 groups
are cis to each other. The synthetic
potential was demonstrated by the total
synthesis of panomifene (Ar1 = Ar3 = Ph,
Ar2 = 4-(OHCH2CH2NHCH2CH2O)-C6H4).
Bpin = (pinacolato)boryl.
Upping the anti: Asymmetric anti-selective hydrogenation of a-amino-b-keto
esters through dynamic kinetic resolution
has been achieved for the first time by
using the Ru–binap catalyst. The reaction
affords important anti-b-hydroxy-a-amino
acids with 74–98 % ee and high diastereomeric ratio in excellent yields (see
scheme; binap = 2,2’-bis(diphenylphosphanyl)-1,1’-binaphthyl).
A Facile Stereocontrolled Approach to CF3Substituted Triarylethenes: Synthesis of
Panomifene
anti-Selective Hydrogenation
K. Makino, T. Goto, Y. Hiroki,
Y. Hamada*
882 – 884
Stereoselective Synthesis of
anti-b-Hydroxy-a-amino Acids through
Dynamic Kinetic Resolution
Biomineralization
The geological longevity of Lingula,
depicted, suggests that the lightly mineralized carbonate-substituted fluorapatite
(FAP) shell has remained well-adapted to
evolutionary pressures. Contrary to earlier
studies, soluble macromolecules isolated
from Lingula shells are shown to specifically promote FAP crystallization by the
destabilization of an amorphous calcium
phosphate precursor.
I. LXvÞque, M. Cusack, S. A. Davis,
S. Mann*
885 – 888
Promotion of Fluorapatite Crystallization
by Soluble-Matrix Proteins from Lingula
Anatina Shells
A mild method for the Ni0-catalyzed
hydrodesulfamoylation (see scheme, B) of
aryl sulfonamides (1!2) with iPr2Mg or
iPrMgCl as b-hydride transfer sources can
be linked with directed ortho metalation (A
and C) to give meta-substituted aromatics
2. Cross-coupling process with alkyl and
aryl Grignard reagents furnish disubstituted benzenes and bi- and teraryl compounds.
Cross-Coupling Reactions
R. R. Milburn, V. Snieckus*
888 – 891
The Tertiary Sulfonamide as a Latent
Directed-Metalation Group: Ni0-Catalyzed
Reductive Cleavage and Cross-Coupling
Reactions of Aryl Sulfonamides with
Grignard Reagents
A potentially good alternative to the tosyl
group (Ts) as a protecting group for
amines is N-ortho-anisylsulfonyl (Ans),
which is readily cleaved under mild, Ni0catalyzed reductive conditions (see
scheme, acac = acetylacetonate). NAnisylation of primary amines followed by
alkylation and deprotection provides a
route to a range of secondary amines.
Angew. Chem. Int. Ed. 2004, 43, 768 – 774
879 – 882
www.angewandte.org
Protecting Groups
R. R. Milburn, V. Snieckus*
892 – 894
ortho-Anisylsulfonyl as a Protecting Group
for Secondary Amines: Mild Ni0-Catalyzed
Hydrodesulfonylation
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
773
Contents
Oligocyclic Dienes
H. W. SBnnemann,
A. de Meijere*
895 – 897
Steroids and Steroid Analogues from
Stille–Heck Coupling Sequences
Tricyclic 1,3,5-hexatrienes were prepared
from 4-substituted 2-bromocyclohexenyl
triflate, enantiomerically pure hexahydroindenylstannanes, and tert-butyl acrylate in a sequence of Stille and Heck
reactions. In the example shown, an
enantiomerically pure steroid with protected functionalities in the 3-, 7-, and 17positions is formed in a 6p-electrocyclization upon heating at 220 8C.
A one-pot reaction sequence consisting of
a Grignard reaction, allylation, and
reduction provides new functionalized
diarylamines in good yields (see scheme,
Ts = toluene-4-sulfonyl, NMP = N-methyl-
pyrrolidine, TFA = trifluoroacetic acid). In
the first step azoaryl tosylates, which are
readily obtained from aromatic amines,
are treated with a myriad of functionalized
organomagnesium compounds.
Amination
I. Sapountzis, P. Knochel*
897 – 900
A General Amination Method Based
on the Addition of Polyfunctional Arylmagnesium Reagents to Functionalized
Arylazo Tosylates
Bioorganic Chemistry
V. Wittmann,* S. Seeberger
900 – 903
Spatial Screening of Cyclic Neoglycopeptides: Identification of Polyvalent WheatGerm Agglutinin Ligands
Affinities enhanced by up to 619-fold were
found for new ligands of the plant lectin
wheat-germ agglutinin (compared to the
binding of N-acetylglucosamine
(GlcNAc)). These polyvalent neoglycopeptides were identified from screening of
a spatially diverse library of type 1. Binding
affinity is determined not only by the
number of GlcNAc residues but also by
the ligand architecture.
Communications labeled with this symbol have been judged by two referees as being “very important papers”.
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Keywords
906
Authors
907
Angewandte’s Sister Journals 904 – 905
Preview
774
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
909
Angew. Chem. Int. Ed. 2004, 43, 768 – 774
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