Cobalt-catalyzed asymmetric hydrogenation of ketones: A remarkable additive effect on enantioselectivity

被引：19
作者：
Du, Tian [1 ]
Wang, Biwen [1 ]
Wang, Chao [1 ]
Xiao, Jianliang [2 ]
Tang, Weijun [1 ]
机构：
[1] Shaanxi Normal Univ, Sch Chem & Chem Engn, Key Lab Appl Surface & Colloid Chem, Minist Educ, Xian 710062, Peoples R China
[2] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England
来源：
CHINESE CHEMICAL LETTERS | 2021年 / 32卷 / 03期
基金：
中国国家自然科学基金;
关键词：
Cobalt; Asymmetric hydrogenation; Ketones; Additive effect; Pincer complex; SELECTIVE HYDROGENATION; AMINO-ALCOHOLS; COMPLEXES; IRON; DEHYDROGENATION; MILD; C=O; LIGANDS; ACID;
D O I：
10.1016/j.cclet.2020.09.011
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A chiral cobalt pincer complex, when combined with an achiral electron-rich mono-phosphine ligand, catalyzes efficient asymmetric hydrogenation of a wide range of aryl ketones, affording chiral alcohols with high yields and moderate to excellent enantioselectivities (29 examples, up to 93% ee). Notably, the achiral mono-phosphine ligand shows a remarkable effect on the enantioselectivity of the reaction. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码：1241 / 1244
页数：4
相关论文
共 52 条
  • [1] A General and Highly Selective Cobalt-Catalyzed Hydrogenation of N-Heteroarenes under Mild Reaction Conditions
    Adam, Rosa
    Cabrero-Antonino, Jose R.
    Spannenberg, Anke
    Junge, Kathrin
    Jackstell, Ralf
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (12) : 3216 - 3220
  • [2] Selective Hydrogenation of Nitriles to Primary Amines by using a Cobalt Phosphine Catalyst
    Adam, Rosa
    Bheeter, Charles Beromeo
    Cabrero-Antonino, Jose R.
    Junge, Kathrin
    Jackstell, Ralf
    Beller, Matthias
    [J]. CHEMSUSCHEM, 2017, 10 (05) : 842 - 846
  • [3] Hydride Transfer Reactions Catalyzed by Cobalt Complexes
    Ai, Wenying
    Zhong, Rui
    Liu, Xufang
    Liu, Qiang
    [J]. CHEMICAL REVIEWS, 2019, 119 (04) : 2876 - 2953
  • [4] Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes
    Chen, Jianhui
    Chen, Chenhui
    Ji, Chonglei
    Lu, Zhan
    [J]. ORGANIC LETTERS, 2016, 18 (07) : 1594 - 1597
  • [5] Catalytic (de)hydrogenation promoted by non-precious metals - Co, Fe and Mn: recent advances in an emerging field
    Filonenko, Georgy A.
    van Putten, Robbert
    Hensen, Emiel J. M.
    Pidko, Evgeny A.
    [J]. CHEMICAL SOCIETY REVIEWS, 2018, 47 (04) : 1459 - 1483
  • [6] Cobalt-catalyzed asymmetric hydrogenation of enamides enabled by single-electron reduction
    Friedfeld, Max R.
    Zhong, Hongyu
    Ruck, Rebecca T.
    Shevlin, Michael
    Chirik, Paul J.
    [J]. SCIENCE, 2018, 360 (6391) : 888 - 892
  • [7] Cobalt-Catalyzed Enantioselective Hydrogenation of Minimally Functionalized Alkenes: Isotopic Labeling Provides Insight into the Origin of Stereoselectivity and Alkene Insertion Preferences
    Friedfeld, Max R.
    Shevlin, Michael
    Margulieux, Grant W.
    Campeau, Louis-Charles
    Chirik, Paul J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (10) : 3314 - 3324
  • [8] Cobalt Precursors for High-Throughput Discovery of Base Metal Asymmetric Alkene Hydrogenation Catalysts
    Friedfeld, Max R.
    Shevlin, Michael
    Hoyt, Jordan M.
    Krska, Shane W.
    Tudge, Matthew T.
    Chirik, Paul J.
    [J]. SCIENCE, 2013, 342 (6162) : 1076 - 1080
  • [9] Ligand-Controlled Cobalt-Catalyzed Transfer Hydrogenation of Alkynes: Stereodivergent Synthesis of Z- and E-Alkenes
    Fu, Shaomin
    Chen, Nan-Yu
    Liu, Xufang
    Shao, Zhihui
    Luo, Shu-Ping
    Liu, Qiang
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (27) : 8588 - 8594
  • [10] Heteroatom-Free Arene-Cobalt and Arene-Iron Catalysts for Hydrogenations
    Gaertner, Dominik
    Welther, Alice
    Rad, Babak Rezaei
    Wolf, Robert
    Jacobi von Wangelin, Axel
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (14) : 3722 - 3726
123456