Manganese(I)-Catalyzed Enantioselective Hydrogenation of Ketones Using a Defined Chiral PNP Pincer Ligand

被引:175
|
作者
Garbe, Marcel [1 ]
Junge, Kathrin [1 ]
Walker, Svenja [1 ]
Wei, Zhihong [1 ]
Jiao, Haijun [1 ]
Spannenberg, Anke [1 ]
Bachmann, Stephan [2 ]
Scalone, Michelangelo [2 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany
[2] F Hoffmann La Roche Ltd, Proc Chem & Catalysis, CH-4070 Basel, Switzerland
关键词
asymmetric hydrogenation; chiral alcohols; chiral pincer ligands; ketones; manganese; ASYMMETRIC TRANSFER HYDROGENATION; C BOND FORMATION; P-N-P'; IRON(II) COMPLEXES; CATALYTIC-HYDROGENATION; EFFICIENT; ALCOHOLS; AMINES; ALKYLATION; REDUCTION;
D O I
10.1002/anie.201705471
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new chiral manganese PNP pincer complex is described. The asymmetric hydrogenation of several prochiral ketones with molecular hydrogen in the presence of this complex proceeds under mild conditions (30-40 degrees C, 4 h, 30 bar H-2). Besides high catalytic activity for aromatic substrates, aliphatic ketones are hydrogenated with remarkable selectivity (e.r. up to 92:8). DFT calculations support an outer sphere hydrogenation mechanism as well as the experimentally determined stereochemistry.
引用
收藏
页码:11237 / 11241
页数:5
相关论文
共 50 条
  • [31] Enantioselective synthesis of chiral β-hydroxy sulfones via manganese catalyzed asymmetric hydrogenation
    He, Jiaying
    Mao, Wenhao
    Lin, Jie
    Wu, Yongzhen
    Chen, Lingxin
    Yang, Pengtao
    Song, Dingguo
    Zhu, Peixi
    Zhong, Weihui
    Ling, Fei
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (13) : 3321 - 3327
  • [32] Efficient Hydrogenation of Ketones Catalyzed by an Iron Pincer Complex
    Langer, Robert
    Leitus, Gregory
    Ben-David, Yehoshoa
    Milstein, David
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (09) : 2120 - 2124
  • [33] Asymmetric Transfer Hydrogenation of Diaryl Ketones with Ethanol Catalyzed by Chiral NCP Pincer Iridium Complexes
    Qian, Lu
    Tang, Xixia
    Wang, Yulei
    Liu, Guixia
    Huang, Zheng
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (10) : 1131 - 1136
  • [34] Highly Enantioselective Synthesis of Chiral Benzhydrols via Manganese Catalyzed Asymmetric Hydrogenation of Unsymmetrical Benzophenones Using an Imidazole-Based Chiral PNN Tridentate Ligand
    Ling, Fei
    Hou, Huacui
    Chen, Jiachen
    Nian, Sanfei
    Yi, Xiao
    Wang, Ze
    Song, Dingguo
    Zhong, Weihui
    ORGANIC LETTERS, 2019, 21 (11) : 3937 - 3941
  • [35] Chemoselective Hydrogenation of α,β-Unsaturated Ketones Catalyzed by a Manganese(I) Hydride Complex
    Dey, Kartick
    de Ruiter, Graham
    ORGANIC LETTERS, 2024, 26 (20) : 4173 - 4177
  • [36] Copper-Catalyzed Enantioselective Hydrogenation of Ketones
    Junge, Kathrin
    Wendt, Bianca
    Addis, Daniele
    Zhou, Shaolin
    Das, Shoubhik
    Fleischer, Steffen
    Beller, Matthias
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (01) : 101 - 105
  • [37] Sustainable Synthesis of Quinolines and Pyrimidines Catalyzed by Manganese PNP Pincer Complexes
    Mastalir, Matthias
    Glatz, Mathias
    Pittenauer, Ernst
    Allmaier, Guenter
    Kirchner, Karl
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (48) : 15543 - 15546
  • [38] Manganese PNP-pincer catalyzed isomerization of allylic/homo-allylic alcohols to ketones - activity, selectivity, efficiency
    Xia, Tian
    Spiegelberg, Brian
    Wei, Zhihong
    Jiao, Haijun
    Tin, Sergey
    Hinze, Sandra
    de Vries, Johannes G.
    CATALYSIS SCIENCE & TECHNOLOGY, 2019, 9 (22) : 6327 - 6334
  • [39] Enantioselective Synthesis of Chiral Fluorinated Amines via Manganese-Catalyzed Asymmetric Hydrogenation
    Hu, Xin-Hu
    Zheng, Kai-Kai
    Yin, Hang
    Wang, Ya-Hui
    Liu, Run-Qiao
    Wang, Kang-Jun
    Weng, Bo-Han
    Zhou, Ming-Dong
    Cai, Gui-Ping
    Guan, Jin
    Yang, Ying
    Su, Jian-Fei
    Jiang, Xin-Dong
    Hu, Xiang-Ping
    ORGANIC LETTERS, 2025,
  • [40] Manganese catalyzed asymmetric transfer hydrogenation of ketones
    Guang-Ya Zhang
    Sun-Hong Ruan
    Yan-Yun Li
    Jing-Xing Gao
    Chinese Chemical Letters, 2021, 32 (04) : 1415 - 1418