Angewandte Chemie International Edition in English

Cover image for Vol. 36 Issue 3

February 14, 1997

Volume 36, Issue 3

Pages 177–299

Currently known as: Angewandte Chemie International Edition

    1. Cover Picture (Angew. Chem. Int. Ed. Engl. 3/1997)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199701751

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      The cover picture shows the molecular structures of two chiral ruthenium complexes that mediate the asymmetric hydrogen transfer between 2-propanol and ketones: on the violet background an amidoruthenium(II) and an amine(hydrido)ruthenium complex (yellow). The examination of the reactivities of the two complexes as well as the kinetics of the rection showed that these two compounds are the only intermediates in this catalytic hydrogen transfer involving secondary alcohols and ketones. In principle this two-component catalytic cycle can continue indefinitely. The structural characteristics and the synthetic utility of these chiral complexes in asymmetric synthesis are discussed by R. Noyori et al. in two communications on pages 285ff. and 288ff.

  1. Reviews

    1. Top of page
    2. Reviews
    3. Highlights
    4. Communications
    5. Book Reviews
    1. Regio- and Stereoselective Syntheses with Organocopper Reagents (pages 186–204)

      Prof. Dr. Norbert Krause and Dipl.-Ing. Andreas Gerold

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199701861

      Organometallic reagents of unsurpassed versatility! Organocooper reagents are superbly suited for stereo- and regioselective syntheses, in particular those based on conjugate additions and SN2′ reactions. They have thus become indispensable in the synthesis of complex natural products and pharmaceuticals, chiral auxiliaries, and molecules with interesting structural features. One of the important new developments in this area is the extension of Michael additions to 1,6-, 1,8-, 1,10-, and 1,12-additions to acetylenic substrates.

    2. Solventothermal Synthesis of Solid-State Chalcogenidometalates (pages 206–224)

      Prof. Dr. William S. Sheldrick and Dipl.-Chem. Michael Wachhold

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702061

      Superheated solvents such as water, methanol, and amines at temperatures in the range 110–220°C provide expedient polar reaction media for the designed construction of chalcogenide-based open-sheet and framework materials. Such conditions greatly enhance solubility, diffusion, and crystallization, but are still mild enough to leave molecular units such as chains and rings intact to participate in the self-assembly of zeolite-like structures. Methanolothermal techniques are particularly suitable for the preparation of Se- and Te-based frameworks.

  2. Highlights

    1. Top of page
    2. Reviews
    3. Highlights
    4. Communications
    5. Book Reviews
    1. New Strategies to α-Alkylated α-Amino Acids (pages 225–227)

      Dr. Thomas Wirth

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702251

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      The repertoire for the synthesis of α-alkylated α-amino acids 1 is restricted, but constantly expanding. Since these amino acids are of interest for the construction of peptides with a fixed conformation, as ligands for enantioselective catalytic aldol reactions, and also from a pharmaceutical point of view, the development of simple methods to synthesize these important, nonproteinogenic amino acids is still a challenge for the synthetic chemist.

  3. Communications

    1. Top of page
    2. Reviews
    3. Highlights
    4. Communications
    5. Book Reviews
    1. Phosphinidine-Bridged Silver Clusters (pages 230–233)

      Prof. Dr. Dieter Fenske and Dr. Falk Simon

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702301

      Clusters containing 18, 45, and 50 silver atoms can be synthesized from the reaction of AgCl with PhP(SiMe3)2 in the presence of PnPr3. The structures of the phosphinidine-bridged silver clusters formed depends upon the temperature and the stoichiometric ratio of the reactants. [ Ag50(PPh)20Cl7P(PnPr3)13] is the biggest known silver cluster and one of the largest structurally characterized cluster complexes to date.

    2. [(HgPtBu)4]3—Synthesis, Structure, and Bonding (pages 233–235)

      Prof. Dr. Reinhart Ahlrichs, Dr. Malte von Arnim, Dr. Jan Eisenmann and Prof. Dr. Dieter Fenske

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702331

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      A phosphinidene-bridged multinuclear mercury complex is now accessible in high yield from the reaction of [Fe(CO)4(HgOAc)2] with tBuP(SiMe3)2. The crystal structure of the title compound is depicted on the right (Hg striped, P black). In order to describe the bonding in this trimer of (HgP) eight-membered rings, the structures of (HgPMe)n clusters (n = 2–6, 8, 12) were calculated by using ab initio methods.

    3. Enantioselective Hydrogen Transfer from a Chiral Tin Hydride to a Prochiral Carbon-Centered Radical (pages 235–236)

      Dipl.-Chem. Michael Blumenstein, Dipl.-Chem. Kay Schwarzkopf and Prof. Dr. Jürgen O. Metzger

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702351

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      Synthetically useful enantiomeric excesses were obtained for the first time in radical reductions with optically active tin hydrides, as illustrated in the reaction of 2 with 1 [Eq. (a)]. Moreover, the reaction, the reaction can also be performed catalytically by using the appropriate tin bromide and Na[B(CN)H3] instead of 1.

    4. A Totally Radical Approach to the Control of Stereochemistry: Coupling of Prochiral Radicals with Chiral Nitroxyl Radicals (pages 237–238)

      Prof. Rebecca Braslau, Leland C. Burrill, Lara K. Mahal and Todd Wedeking

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702371

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      Differentiation between the two enantiotopic faces of prochiral carbon radicals by optically active nitroxyl radicals is demonstrated in this novel approach to the control of stereochemistry. In the first experiments, the steroid nitroxyl radical shown in Equation (a) gave selectivities of up to 92:8.

    5. Cyclic and Cubic Organophosphonates of Gallium and Their Relationship to Structural Motifs in Gallophosphate Molecular Sieves (pages 239–241)

      Prof. Mark R. Mason, Dr. Mark S. Mashuta and Prof. John F. Richardson

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702391

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      A potential precursor to new gallophosphate materials. The Cubic Ga4P4O12 unit common to several gallophosphate molecular sieves has now been prepared in a soluble, molecular form. On the right is shown the Ga4P4O12 core of [tBuGa(μ3-O3PPh)]4 as confirmed by X-ray crystallography.

    6. A Cage Molecule with a Cubanoid P4B4 Framework: tBu4P4Ph4B4O12—A Structural Analogue of the Isovalence Electronic Organosilasesquioxanes R8Si8O12 (pages 241–243)

      Dr. Klaus Diemert, Dr. Ulli Englert, Prof. Dr. Wilhelm Kuchen and Dr. Frank Sandt

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702411

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      Molecules that behave like large atoms!—molecules of the mixed anhydride formed from the acids tBuP(O)(OH)2 and PhB(OH)2 exhibit this characteristic since in the crystal lattice they occupy the corners and centers of weakly distorted cubooctahedra. The molecules reveal a cubane framework (depicted on the right), whose corners are occupied alternately by phosphorus and boron atoms and whose edges are bridged by oxygen atoms.

    7. Direct Observation of a Dissociative Mechanism for C[BOND]H Activation by a Cationic Iridium(III) Complex (pages 243–244)

      Christian Hinderling, Dr. Dietmar A. Plattner and Prof. Dr. Peter Chen

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702431

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      An unexpected dissociative mechanism was found for the alkane activation reaction by cation 1 in the gas phase. The reactivity of 1 was studied by electrospray ionization of dilute solutions of [1(N[TRIPLE BOND]CCH3)]+ClOmath image. The reaction proceeds via the reactive cyclic IrIII complex 2, which then adds to the C[BOND]H bonds of saturated and aromatic hydrocarbons to form 3.

    8. Stereoselective Preparation and Reactions of Cycloalkylzinc Compounds (pages 245–246)

      Dr. Laurent Micouin, Martin Oestreich and Prof. Dr. Paul Knochel

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702451

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      Configurationally well-defined cycloalkylzinc compounds (1) were prepared for the first time olefins by hydroboration and subsequent boron–zinc exchange with iPr2Zn. The resulting secondary alkylzinc reagents are configurationally stable and can be allylated or alkynylated stereoselectively in the presence of CuCN · 2LiCl with retention of configuration (see the example below).

    9. An Acentric, Three-Dimensional Coordination Polymer: Synthesis and Structure of [Cu(pyrimidine)2]BF4 (pages 247–248)

      Prof. Steven W. Keller

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702471

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      Coordination networks that mimic silicate mineral structures are formed by a new class of coordination polymers, which are accessible through the self-assembly of tetrahedral copper(I) cations and bent, bifunctional pyrimidine ligands. Thus, extended organometallic frameworks can be produced, which show optical activity (as quartz), or microporosity (as zeolites)…or both! The first example of such a framework is [Cu(pyrimidine)2]BF4 (depicted on the right), which can be described as a “stuffed feldspar”, and contains channels that house both BFmath image ions and disordered solvent molecules.

    10. Phenyl–Perfluorophenyl Stacking Interactions: A New Strategy for Supermolecule Construction (pages 248–251)

      Dr. Geoffrey W. Coates, Alex R. Dunn, Lawrence M. Henling, Prof. Dennis A. Dougherty and Prof. Dr. Robert H. Grubbs

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702481

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      Photochemically induced polymerizations in the solid state of 1 · 2 and 3 depend on the intriguing interaction between phenyl and perfluorophenyl groups, which leads to an appropriate alignment of the molecules in the crystal. As with the 1:1 complex of benzene and hexafluorobenzene the diyne monomers are stacked alternately to form columns of arene groups.

    11. Five-Coordinate Sulfur in a Polymeric Copper(I) Thiolate Complex (pages 251–253)

      Dr. Richard V. Parish, Zahra Salehi and Dr. Robin G. Pritchard

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702511

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      Strong electron-deficient bonds with four equivalent copper(I) centers as well as the carbon atom of the organic group are a feature of the thiolate sulfur atoms of the new cage [(CuCl)12(SR)6] (R [DOUBLE BOND] CH2CH2NH3; structure on the right, Cl and R omitted). This is part of the polymeric complex [Cu13Cl13(SR)6], which is accessible from cysteamine hydrochloride and copper(I) chloride. • = Cu, ○ = S.

    12. A New Asymmetric Formylation of Aldehydes (pages 253–255)

      Dr. Andreas Kirschning, Gerald Dräger and Alexander Jung

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702531

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      Efficient asymmetric formylation of aldehydes is possible by Horner–Wittig homologation of aldehydes and subsequent Sharpless asymmetric dihydroxylation of the intermediate prochiral ketene acetals 2. As is demonstrated for compounds 1, this novel sequence allows synthesis of α-hydroxy carboxylates 3 in high enantiomeric purity.

    13. Constitution of the Iodyl Cation (pages 255–256)

      Prof. Dr. Martin Jansen and Dipl.-Chem. Ralph Müller

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702551

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      Unexpectedly a dimeric structure is found for the iodyl cation in (IO2)2S2O7. For the first time a representative of this type of complex cation could be characterized by X-ray crystal structure analysis (see picture). The description as an ionic crystal comprising (IO2)math image and S2Omath image is an oversimplification because of the strong intramolecular bonds forming a polymeric network.

    14. Selective Ring-Opening Olefin Metathesis of Functionalized Monosubstituted Olefins (pages 257–259)

      Dr. Matthias F. Schneider, Dipl.-Chem. Norbert Lucas, Dr. Janna Velder and Prof. Dr. Siegfried Blechert

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702571

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      Not only high selectivity, but also atom economy are the attractive features of this synthetic strategy. Most crossed olefin metatheses between strained and monosubstituted olefins can be carried out with Grubbs's or Schrock's catalyst ([Ru] and [Mo], respectively, see below) even when the ratio of starting materials is 1:1! The high tolerance displayed towards many functional groups makes the prospect of subsequent reactions exciting.

    15. New Supramolecular Complex of C60 Based on Calix[5]arene—Its Structure in the Crystal and in Solution (pages 259–260)

      Dr. Takeharu Haino, Manabu Yanase and Prof. Dr. Yoshimasa Fukazawa

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702591

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      Usually the host, C60 is here the guest in a complex between C60 and calix[5]arenes (see picture) that was studied both in solution and in the solid state. In solution, as disclosed by the ring current method of analysis for 13C NMR spectra based on the X-ray crystallographic analysis, van der Waals interactions between the host and guest play an important role in the complexation.

    16. A Dinuclear Tin(II) Amide, a meta-Stannylaminocyclophane and Its Orthostannylated Derivative, a Dimeric Trinuclear Tin(II) Cluster (pages 261–263)

      Dr. Holger Braunschweig, Dr. Christian Drost, Dr. Peter B. Hitchcock, Prof. Michael F. Lappert and Luc J.-M. Pierssens

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702611

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      A nearly equilateral triangle is formed by the three Sn atoms in 1. This complex is the product of a hitherto unknown 2-stannylation of a 1,3-diaminobenzene and is thus of general significance in the context of the metalation of arenes. R [DOUBLE BOND] SiMe3.

    17. Highly Selective Allylic Alkylation with a Carbon Nucleophile at the More Substituted Allylic Terminus Catalyzed by an Iridium Complex: An Efficient Method for Constructing Quaternary Carbon Centers (pages 263–265)

      Prof. Dr. Ryo Takeuchi and Mikihiro Kashio

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702631

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      The selective construction of quaternary carbon centers, which are frequently found in natural products, is essential to many syntheses. A new method relying on the iridium complex [Ir(cod)Cl]2 as the catalyst can be used for the allylic alkylation of acyclic compounds 1 [Eq (a)]. The products are obtained in yields between 70 and 85% and with a selectivity of 100%. cod = cyclooctadiene.

    18. Dihydrogen Formation in a Trihydride Metallocene and Its Elimination, Both Assisted by Lewis Acids: The [Cp2NbH3]+BH3 System (pages 265–266)

      Dipl.-Chem. Santiago Camanyes, Dr. Feliu Maseras, Dr. Miquel Moreno, Prof. Dr. Agustí Lledós, Prof. Dr. José M. Lluch and Prof. Dr. Juan Bertrán

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702651

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      Theoretical evidence confirms the large influence that a Lewis acid (here BH3) exerts on the type of H-coordination in metallocene trihydrides (here [Cp2NbH3]). The coordination of the Lewis acid facilitates both the formation of a dihydrogen structure (1) and the loss of a hydrogen molecule. This could be useful in the storage or elimination of molecular hydrogen using transition metal complexes.

    19. Defining the Conformation of Lewis Acid/Lewis Base Complex: Crystallographic Evidence for Simultaneous σ and π Donation by a Carbonyl Group to a Divalent Boron Lewis Acid (pages 267–269)

      Michael C. Amendola, Dr. Kenneth E. Stockman, Diego A. Hoic, Dr. William M. Davis and Prof. Dr. Gregory C. Fu

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702671

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      An additional π-symmetry interaction can define the conformation of a complex formed between a carbonyl compound and a Lewis acid. This was demonstrated in studies of the borabanzene adduct 1 in solution and in the solid state. Studies like this are relevant to the design of effective chiral Lewis acid catalysts.

    20. A Tandem Approach to Graft and Dendritic Graft Copolymers Based on “Living” Free Radical Polymerizations (pages 270–272)

      Robert B. Grubbs, Dr. Craig J. Hawker, Julian Dao and Prof. Dr. Jean M. J. Fréchet

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702701

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      Owing to their inherent differences, consecutive “living” free radical polymerizations can yield graft and dendritic graft (dendrigraft) copolymers with multiple chain-end functionalities such as that shown schematically on the right (PS = polystyrene), PBMA = poly(n-butyl methylmethacrylate). The first polymerization leads to the linear backbone, and subsequent polymerizations introduce grafted chains.

    21. The Xemath image Ion—Preparation and Structure (pages 273–274)

      Thomas Drews and Prof. Dr. Konrad Seppelt

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702731

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      One of the longest element–element bonds is present in the Xemath image ion, which had been predicted by theoretical calculations and detected by mass spectrometry as well as by ESR spectroscopy in solution. The cation occurs in Xemath imageSb4Fmath image (depicted on the right), which has been obtained as dark green crystals. The Xe[BOND]Xe bond length (308.7(1) pm) is significantly shorter than theoretically predicted (317–327 pm).

    22. Regio- and Stereocontrolled Conjugate Radical Addition to a Desymmetrized Fumarate Derivative: An Efficient Synthesis of (−)-Nephrosteranic Acid and (−)-Roccellaric Acid (pages 274–276)

      Prof. Mukund P. Sibi and Dr. Jianguo Ji

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702741

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      Multiple stereocenters can be introduced with high selectivity by lanthanide Lewis acid mediated conjugate radical addition to a desymmetrized fumarate derivative (step 1 in the reaction sequence below) followed by an aldol reaction (step 2). The regio- and stereoselectivities of the first step with Sm(OTf)3, Tm(OTf)3, and Er(OTf)3 are particularly impressive (> 100:1 and ≤47:1, respectively). This method was also applied in the synthesis of the trisubstituted butyrolactone natural products mentioned in the title. Tf = CF3SO2, Xc = chiral auxiliary.

    23. Direct Proof of trans-Diazene in Solution by Trapping and Isolation of the Trapping Products (pages 276–278)

      Prof. Dr. Dieter Sellmann and Dipl.-Chem. Andreas Hennige

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702761

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      Diazene was trapped for the first time from solution by coordination to the complex [Fe(PPr3)-(SC6H4SCH2CH2SC6H4S)] (generated in situ) to form 1 in which it is in the trans configuration! This raises the question whether the cis-diazene structure postulated for N2H2 in solution is really indispensable to explain the stereoselective cis hydrogenations of multiple bonds by diazene.

    24. Alkali Metal Complexes of o, o′-(Tetraethyleneglycoldiyl)-(Z)-stilbene: One Common Ligand Conformation for Li, Na, K, and Rb Ions (pages 278–280)

      Prof. Dr. Andreas Merz, Dipl.-Chem. Thomas Futterer, Dr. Johann Lex and Dr. Halina Inerowicz

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702781

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      Though apparently a strange structural feature, the (Z)-stilbene unit is in fact a hinge that determines the shape of the title crown ether. Alkali metal ions from Li to Rb are accomodated in the conformation depicted on the right (spheres in the cavity illustrate the relative sizes of the ions); the crown compound shows high lithium selectivity.

    25. From Hünig's Base to Bis([1,2]dithiolo)-[1,4]thiazines in One Pot: The Fast Route to Highly Sulfurated Heterocycles (pages 281–283)

      Prof. Charles W. Rees, Dr. Carlos F. Marcos, Dr. Cecilia Polo, Dr. Tomás Torroba and Dr. Oleg A. Rakitin

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702811

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      In an extremely complex sequence of roughly 15 reaction steps ethyldiisopropylamine (Hü;nig's base) reacts with disulfur dichloride to give thiazine 1 [Eq. (a)]. Remarkable features of this reaction are the selectivity (only the isopropyl groups are attacked), the mild conditions relative to those in other diol syntheses, and the overall yield of 40%.

    26. New Surprises with Fischer Carbene Complexes: Formal [3+2] Cycloadditions with and without Preeceding Carben–Ligand Matathesis (pages 283–285)

      Dr. Matthias Hoffmann, Prof. Dr. Hans-Ulrich Reissig and Dr. Matthias Buchert

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702831

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      The metal-induced dimerization of dienes with explusion of “CH2” is a formal description of the reaction of Fischer carbene complexes with certain solixydienes [Eq. (a)]. The key steps in the reaction are carbene ligand metathesis (the original carbene ligand is not incorporated in the product) and a highly diastereoselective [3 + 2]cycloaddition. TBS = tBuMe2Si; R = Ph, Me; R′ = Co2Me, Ph.

    27. The Catalyst Precursor, Catalyst, and Intermediate in the RuII-Promoted Asymmetric Hydrogen Transfer between Alcohols and Ketones (pages 285–288)

      Dr. Karl-Josef Haack, Dr. Shohei Hashiguchi, Dr. Akio Fujii, Dr. Takao Ikariya and Prof. Dr. Ryoji Noyori

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702851

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      New insight into the mechanism of catalysis. The purple 16-electron complex 1 and the yellow 18-electron complex 2 directly mediate the asymmetric, RuII-catalyzed hydrogen transfer between secondary alcohols and ketones. Both complexes were characterized by X-ray crystallography.

    28. Kinetic Resolution of Racemic Secondary Alcohols by RuII-Catalyzed Hydrogen Transfer (pages 288–290)

      Dr. Shohei Hashiguchi, Dr. Akio Fujii, Dr. Karl-Josef Haack, Kazuhiko Matsumura, Dr. Takao Ikariya and Prof. Dr. Ryoji Noyori

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702881

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      Acetone serves as the hydrogen acceptor in the kinetic resolution of racemic alcohols catalyzed by a chiral RuII complex. This method provides access to alcohols that are not available from the corresponding ketones by standard enantioselective reduction (examples of substrates are given on the right) and is particularly interesting for meso compounds. R1 [DOUBLE BOND] (CH3)2N, R2 [DOUBLE BOND] H, CH3.

    29. The High Nuclearity Mixed–Metal Cluster Dianions [Ru8H2Cu7Cl3(CO)24]2− and [Ru12H2Cu6Cl2(CO)34]2− (pages 291–293)

      Dr. Michael A. Beswick, Prof. the Lord Jack Lewis, Dr. Paul R. Raithby and Dr. M. Carmen Ramirez de Arellano

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199702911

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      A linear arrangement of condensed octahedra and fused square-based pyramids are present in the novel, high nuclearity, mixed-metal dianions of the title (2 and 1, respectively), which are formed in the rection of [Ru6H(CO)18] with excess [Cu(MeCN)4]+ in the presence of chloride ions in CH2Cl2 (1) and CH3CN (2). In these dianions the metallic ruthenium cluster cores are fused together through a central copper cluster unit (metal cores of (1 (left) and 2 (right) are depicted below).

  4. Book Reviews

    1. Top of page
    2. Reviews
    3. Highlights
    4. Communications
    5. Book Reviews