Advanced Synthesis & Catalysis

Cover image for Vol. 354 Issue 18

December 14, 2012

Volume 354, Issue 18

Pages 3337–3567

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Corrigendum
    5. Review
    6. Communications
    7. Full Papers
    8. Updates
    1. You have free access to this content
      Cover Picture: (Adv. Synth. Catal. 18/2012) (page 3337)

      Version of Record online: 12 DEC 2012 | DOI: 10.1002/adsc.201290035

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      The cover picture, provided by Qi-Lin Zhou, shows the example of an exceptionally highly efficient chiral catalyst. The catalyst is a very stable dihydride iridium complex of a tridentate chiral spiro P-N-N ligand based on the 1,1′-spirobiindane skeleton, which exhibits excellent enantioselectivity and extremely high turnover number (in excess of one million) for the hydrogenation of both aryl ketones and β-aryl-β-keto esters. Although little is known about the mechanism of this iridiumcatalyzed carbonyl group hydrogenation reaction, a non-classical metal[BOND]ligand bifunctional mechanism deserves to be recommended to interpret the high efficiency of this catalyst. With the help of KO-t-Bu and under an H2 atmosphere, the dihydride iridium complex is converted to a trihydride iridium complex. After combination of the substrate with the trihydride iridium complex, a cyclic six-membered transition state is formed. The hydridic Ir[BOND]H and protic N[BOND]H of the catalyst are simultaneously transferred to the carbonyl[BOND]oxygen double bond of the substrate, resulting in a chiral alcohol and a hydrido amido iridium complex. Finally, the hydrido amido iridium complex is hydrogenated with H2 to regenerate the trihydride iridium complex.

  2. Contents

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Corrigendum
    5. Review
    6. Communications
    7. Full Papers
    8. Updates
  3. Corrigendum

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Corrigendum
    5. Review
    6. Communications
    7. Full Papers
    8. Updates
    1. You have free access to this content
  4. Review

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Corrigendum
    5. Review
    6. Communications
    7. Full Papers
    8. Updates
    1. Recent Developments in Enantioselective Metal-Catalyzed Domino Reactions (pages 3347–3403)

      Hervé Clavier and Hélène Pellissier

      Version of Record online: 14 NOV 2012 | DOI: 10.1002/adsc.201200254

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  5. Communications

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Corrigendum
    5. Review
    6. Communications
    7. Full Papers
    8. Updates
    1. From Diols to Lactones under Aerobic Conditions using a Laccase/TEMPO Catalytic System in Aqueous Medium (pages 3405–3408)

      Alba Díaz-Rodríguez, Iván Lavandera, Seda Kanbak-Aksu, Roger A. Sheldon, Vicente Gotor and Vicente Gotor-Fernández

      Version of Record online: 4 DEC 2012 | DOI: 10.1002/adsc.201200892

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    2. Asymmetric Bio-amination of Ketones in Organic Solvents (pages 3409–3413)

      Francesco G. Mutti and Wolfgang Kroutil

      Version of Record online: 28 NOV 2012 | DOI: 10.1002/adsc.201200900

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    3. A New Family of Conformationally Constrained Bicyclic Diarylprolinol Silyl Ethers as Organocatalysts (pages 3428–3434)

      Marco Lombardo, Elisa Montroni, Arianna Quintavalla and Claudio Trombini

      Version of Record online: 28 NOV 2012 | DOI: 10.1002/adsc.201200922

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    4. Water-Soluble Chiral Ruthenium(II) Phenyloxazoline Complex: Reusable and Highly Enantioselective Catalyst for Intramolecular Cyclopropanation Reactions (pages 3435–3439)

      Abdel-Moneim Abu-Elfotoh, Diem Phuong Thi Nguyen, Soda Chanthamath, Kesiny Phomkeona, Kazutaka Shibatomi and Seiji Iwasa

      Version of Record online: 4 DEC 2012 | DOI: 10.1002/adsc.201200508

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    5. Highly Active Dinuclear Copper Catalysts for Homogeneous Azide–Alkyne Cycloadditions (pages 3445–3450)

      Regina Berg, Johannes Straub, Ella Schreiner, Steffen Mader, Frank Rominger and Bernd F. Straub

      Version of Record online: 28 NOV 2012 | DOI: 10.1002/adsc.201200734

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    6. Cross-Coupling in Flow using Supported Catalysts: Mild, Clean, Efficient and Sustainable Suzuki–Miyaura Coupling in a Single Pass (pages 3456–3460)

      Juan de M. Muñoz, Jesús Alcázar, Antonio de la Hoz and Angel Díaz-Ortiz

      Version of Record online: 28 NOV 2012 | DOI: 10.1002/adsc.201200678

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  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Corrigendum
    5. Review
    6. Communications
    7. Full Papers
    8. Updates
    1. Quantitative Comparison of Chiral Catalysts Selectivity and Performance: A Generic Concept Illustrated with Cyclododecanone Monooxygenase as Baeyer–Villiger Biocatalyst (pages 3491–3500)

      Michael J. Fink, Daniela V. Rial, Petra Kapitanova, Alenka Lengar, Jessica Rehdorf, Qiong Cheng, Florian Rudroff and Marko D. Mihovilovic

      Version of Record online: 21 NOV 2012 | DOI: 10.1002/adsc.201200453

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    2. Sulfation of Various Alcoholic Groups by an Arylsulfate Sulfotransferase from Desulfitobacterium hafniense and Synthesis of Estradiol Sulfate (pages 3501–3508)

      Michael A. van der Horst, Johan F. T. van Lieshout, Aleksandra Bury, Aloysius F. Hartog and Ron Wever

      Version of Record online: 4 DEC 2012 | DOI: 10.1002/adsc.201200564

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    3. Enantioselective Organocatalytic Michael Addition of Cyclobutanones to Nitroalkenes (pages 3523–3532)

      Damien Mailhol, Maria del Mar Sanchez Duque, Wilfried Raimondi, Damien Bonne, Thierry Constantieux, Yoann Coquerel and Jean Rodriguez

      Version of Record online: 4 DEC 2012 | DOI: 10.1002/adsc.201200658

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    4. Palladium-Catalysed Intramolecular Direct Arylation of 2-Bromobenzenesulfonic Acid Derivatives (pages 3533–3538)

      Charles Beromeo Bheeter, Jitendra K. Bera and Henri Doucet

      Version of Record online: 4 DEC 2012 | DOI: 10.1002/adsc.201200793

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    5. Synthesis and Functionalization of Unsymmetrical Arylsulfonyl Bisindoles and Bisbenzazoles (pages 3539–3544)

      Stefano Lancianesi, Alessandro Palmieri and Marino Petrini

      Version of Record online: 4 DEC 2012 | DOI: 10.1002/adsc.201200632

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  7. Updates

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Corrigendum
    5. Review
    6. Communications
    7. Full Papers
    8. Updates
    1. Batch Stille Coupling with Insoluble and Recyclable Stannylated Polynorbornenes (pages 3551–3560)

      Sheila Martínez-Arranz, Nora Carrera, Ana C. Albéniz, Pablo Espinet and Alejandro Vidal-Moya

      Version of Record online: 4 DEC 2012 | DOI: 10.1002/adsc.201200624

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    2. The Reaction of Tertiary Anilines with Maleimides under Visible Light Redox Catalysis (pages 3561–3567)

      Xuhui Ju, Dianjun Li, Weifei Li, Wei Yu and Fengling Bian

      Version of Record online: 4 DEC 2012 | DOI: 10.1002/adsc.201200608

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