Advanced Synthesis & Catalysis

Cover image for Vol. 355 Issue 8

May 17, 2013

Volume 355, Issue 8

Pages 1437–1660

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Contents
    4. Communications
    5. Full Papers
    6. Updates
    1. You have free access to this content
      Cover Picture: (Adv. Synth. Catal. 8/2013) (page 1437)

      Version of Record online: 24 MAY 2013 | DOI: 10.1002/adsc.201390014

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      The front cover picture, provided by Maurizio Taddei, Marcello Rasparini and coauthors, illustrates the asymmetric hydrogenation of E-enol acetates to β-acetoxy carboxylic acids and subsequently to β-hydroxy acids. These novel hydrogenation substrates, reduced under the catalysis of a [Rh(S)-Phanephos(cod)]complex, are prepared from racemic substituted β-keto esters. The catalyst-substrate interaction is so strong that hydrogenation can be successfully accelerated using microwave dielectric heating, allowing decrease of the hydrogen pressure while maintainingees in excess of 95%. These results conclusively confirm that it is possible to carry out enantioselective synthesis in microwave ovens. The presence of stereocenters and large substituents on the substrate does not interfere with the enantioselectivty of hydrogenation. The process, scaled up to 6 g of substrate using microwaves and to larger quantities using standard autoclaves (under 30 bar of hydrogen), was applied to the production of Aliskiren (Novartis), the first direct renin inhibitor which is used as a treatment for hypertension. Details of this work can be found in the communication by Taddei, Rasparini and co-authors on pages 1449–1454 (DOI:10.1002/adsc.201200934).

    2. You have free access to this content
      Inside Cover Picture: (Adv. Synth. Catal. 8/2013) (page 1438)

      Version of Record online: 27 MAY 2013 | DOI: 10.1002/adsc.201390017

      Thumbnail image of graphical abstract

      The inside front cover picture, provided by Carl A. Busacca and co-workers, depicts an energy-minimized iridium hydride complex of BIPI 238 with the dimethylindene substrate bound in the lower right quadrant. Cationic iridium catalysts containing BIPI ligands with a naphthyl core have been developed as highly enantioselective asymmetric hydrogenation catalysts. The naphthyl peri position has been identified as a critical stereocontrol element in the hydrogenation of tetrasubstituted, unfunctionalized olefins. It is believed to act by restricting the available conformations of the dicyclohexylphosphine group. The peri-fluoro ligand BIPI 238 is one of the most selective ligands found, as shown in the communication by Busacca and co-workers on pages 1455–1463 (DOI: 10.1002/adsc.201201104).

    3. You have free access to this content
      Inside Cover Picture: (Adv. Synth. Catal. 8/2013) (page 1438)

      Version of Record online: 24 MAY 2013 | DOI: 10.1002/adsc.201390015

      Thumbnail image of graphical abstract

      The inside front cover picture, provided by Carl A. Busacca and co-workers, depicts an energy-minimized iridium hydride complex of BIPI 238 with the dimethylindene substrate bound in the lower right quadrant. Cationic iridium catalysts containing BIPI ligands with a naphthyl core have been developed as highly enantioselective asymmetric hydrogenation catalysts. The naphthyl peri position has been identified as a critical stereocontrol element in the hydrogenation of tetrasubstituted, unfunctionalized olefins. It is believed to act by restricting the available conformations of the dicyclohexylphosphine group. The peri-fluoro ligand BIPI 238 is one of the most selective ligands found, as shown in the communication by Busacca and co-workers on pages 1455–1463 (DOI: 10.1002/adsc.201201104).

  2. Contents

    1. Top of page
    2. Cover Pictures
    3. Contents
    4. Communications
    5. Full Papers
    6. Updates
    1. You have free access to this content
  3. Communications

    1. Top of page
    2. Cover Pictures
    3. Contents
    4. Communications
    5. Full Papers
    6. Updates
    1. Rhodium-Catalyzed Enantioselective Hydrogenation of (E)-Enol Acetate Acids (pages 1449–1454)

      Giada Arena, Giuseppe Barreca, Luca Carcone, Elena Cini, Giovanni Marras, Hans G. Nedden, Marcello Rasparini, Stephen Roseblade, Adele Russo, Maurizio Taddei and Antonio Zanotti-Gerosa

      Version of Record online: 22 FEB 2013 | DOI: 10.1002/adsc.201200934

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    2. Tuning the Peri Effect for Enantioselectivity: Asymmetric Hydrogenation of Unfunctionalized Olefins with the BIPI Ligands (pages 1455–1463)

      Carl A. Busacca, Bo Qu, Nicole Grět, Keith R. Fandrick, Anjan K. Saha, Maurice Marsini, Diana Reeves, Nizar Haddad, Magnus Eriksson, Jiang-Ping Wu, Nelu Grinberg, Heewon Lee, Zhibin Li, Bruce Lu, Dajun Chen, Yaping Hong, Shengli Ma and Chris H. Senanayake

      Version of Record online: 20 MAR 2013 | DOI: 10.1002/adsc.201201104

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    3. Building Functionality through Sequential C[BOND]B and C[BOND]F Bond Formation (pages 1464–1470)

      Gerard Palau-Lluch and Elena Fernández

      Version of Record online: 17 MAY 2013 | DOI: 10.1002/adsc.201300282

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    4. Synthesis of 2-Substituted Benzothiazoles by Visible Light-Driven Photoredox Catalysis (pages 1471–1476)

      Chunghyeon Yu, Kyungyub Lee, Youngmin You and Eun Jin Cho

      Version of Record online: 16 MAY 2013 | DOI: 10.1002/adsc.201300376

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    5. Visible-Light Photocatalytic Reduction of Sulfonium Salts as a Source of Aryl Radicals (pages 1477–1482)

      Simon Donck, Abdulkader Baroudi, Louis Fensterbank, Jean-Philippe Goddard and Cyril Ollivier

      Version of Record online: 17 MAY 2013 | DOI: 10.1002/adsc.201300040

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    6. The Copper-Catalyzed Oxidative N-Acylation of Sulfoximines (pages 1490–1494)

      Long Wang, Daniel L. Priebbenow, Liang-Hua Zou and Carsten Bolm

      Version of Record online: 17 MAY 2013 | DOI: 10.1002/adsc.201300273

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    7. Synthesis of N-Arylamides by Copper-Catalyzed Amination of Aryl Halides with Nitriles (pages 1495–1499)

      Shi-Kai Xiang, Dong-Xue Zhang, Hao Hu, Jiang-Ling Shi, Li-Guo Liao, Chun Feng, Bi-Qin Wang, Ke-Qing Zhao, Ping Hu, Hua Yang and Wen-Hao Yu

      Version of Record online: 17 MAY 2013 | DOI: 10.1002/adsc.201300189

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    8. Relay Redox and Lewis Acid Catalysis in the Titanocene- Catalyzed Multicomponent Assembly of 1,5-Enynes (pages 1500–1504)

      Antonio J. Lepore, David M. Pinkerton and Brandon L. Ashfeld

      Version of Record online: 16 MAY 2013 | DOI: 10.1002/adsc.201300359

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    9. Palladium(II)/Polyoxometalate-Catalyzed Direct C-3 Alkenylation of Indoles using Dioxygen as the Terminal Oxidant (pages 1512–1516)

      Qiufeng Huang, Qianqian Song, Jin Cai, Xiaofeng Zhang and Shen Lin

      Version of Record online: 15 MAY 2013 | DOI: 10.1002/adsc.201201114

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    10. Palladium-Catalyzed Decarboxylative Coupling of α- Oxocarboxylic Acids with C(sp2)[BOND]H of 2-Aryloxypyridines (pages 1517–1522)

      Jinzhong Yao, Ruokun Feng, Zaihong Wu, Zhanxiang Liu and Yuhong Zhang

      Version of Record online: 17 MAY 2013 | DOI: 10.1002/adsc.201300078

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    11. Platinum on Carbon-Catalyzed H–D Exchange Reaction of Aromatic Nuclei due to Isopropyl Alcohol-Mediated Self- Activation of Platinum Metal in Deuterium Oxide (pages 1529–1534)

      Yoshinari Sawama, Tsuyoshi Yamada, Yuki Yabe, Kosuke Morita, Kyoshiro Shibata, Masahiro Shigetsura, Yasunari Monguchi and Hironao Sajiki

      Version of Record online: 15 MAY 2013 | DOI: 10.1002/adsc.201201102

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    12. Superbase-Catalyzed [4+2] Cycloaddition of Acetylenes to 3,6-Di(pyrrol-2-yl)-1,2,4,5-tetrazine: A Facile Synthesis of 3,6-Di(pyrrol-2-yl)pyridazines (pages 1535–1539)

      Boris A. Trofimov, Tatyana E. Glotova, Dmitrii A. Shabalin, Marina Yu. Dvorko, Igor A. Ushakov, Elena Yu. Schmidt, Anton V. Kuzmin and Al'bina I. Mikhaleva

      Version of Record online: 15 MAY 2013 | DOI: 10.1002/adsc.201300129

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    13. Bicyclization of Diazomethanes: A Synthetic Strategy for Fused Pyrazoles (pages 1540–1544)

      He Wang, Yu-Long Zhao, Lei Li, Zhen-Wei Zhang and Qun Liu

      Version of Record online: 15 MAY 2013 | DOI: 10.1002/adsc.201201062

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  4. Full Papers

    1. Top of page
    2. Cover Pictures
    3. Contents
    4. Communications
    5. Full Papers
    6. Updates
    1. Palladium-Catalyzed Regioselective and Stereoselective Oxidative Heck Arylation of Allylamines with Arylboronic Acids (pages 1570–1578)

      Lingjuan Zhang, Chaonan Dong, Chenjun Ding, Jing Chen, Weijun Tang, Huanrong Li, Lijin Xu and Jianliang Xiao

      Version of Record online: 15 MAY 2013 | DOI: 10.1002/adsc.201300225

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    2. Tandem Gold-Catalyzed Hydrosilyloxylation–Aldol and –Mannich Reaction with Alkynylaryloxysilanols in 6-exo Mode (pages 1585–1596)

      Euichul Lee, Taekyu Ryu, Youngchul Park, Sangjune Park and Phil Ho Lee

      Version of Record online: 15 MAY 2013 | DOI: 10.1002/adsc.201300244

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    3. Catalytic Asymmetric Hydrogenation of α-Arylcyclohexanones and Total Synthesis of (−)-α-Lycorane (pages 1597–1604)

      Gang Li, Jian-Hua Xie, Jing Hou, Shou-Fei Zhu and Qi-Lin Zhou

      Version of Record online: 15 MAY 2013 | DOI: 10.1002/adsc.201300165

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  5. Updates

    1. Top of page
    2. Cover Pictures
    3. Contents
    4. Communications
    5. Full Papers
    6. Updates
    1. Ethynylbenziodoxolones (EBX) as Reagents for the Ethynylation of Stabilized Enolates (pages 1631–1639)

      Davinia Fernández González, Jonathan P. Brand, Régis Mondière and Jérôme Waser

      Version of Record online: 15 MAY 2013 | DOI: 10.1002/adsc.201300266

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    2. Selective Intramolecular Palladium(II)-Catalyzed Aminooxygenation vs. Diamination of Alkenylureas: Efficient Microwave-Assisted Reactions to Bicyclic Piperazinones (pages 1640–1648)

      Gianluigi Broggini, Vincenzina Barbera, Egle M. Beccalli, Ugo Chiacchio, Andrea Fasana, Simona Galli and Silvia Gazzola

      Version of Record online: 15 MAY 2013 | DOI: 10.1002/adsc.201300104

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    3. Efficient and Green Route to γ-Lactams by Copper-Catalysed Reversed Atom Transfer Radical Cyclisation of α-Polychloro-N-allylamides, using a Low Load of Metal (0.5 mol%) (pages 1649–1660)

      Franco Bellesia, Andrew J. Clark, Fulvia Felluga, Armando Gennaro, Abdirisak A. Isse, Fabrizio Roncaglia and Franco Ghelfi

      Version of Record online: 15 MAY 2013 | DOI: 10.1002/adsc.201300132

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