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

被引:22
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
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
[41]   Catalytic Homogeneous Asymmetric Hydrogenation: Successes and Opportunities [J].
Seo, Chris S. G. ;
Morris, Robert H. .
ORGANOMETALLICS, 2019, 38 (01) :47-65
[42]   General and Phosphine-Free Cobalt-Catalyzed Hydrogenation of Esters to Alcohols [J].
Shao, Zhihui ;
Zhong, Rui ;
Ferraccioli, Raffaella ;
Li, Yibiao ;
Liu, Qiang .
CHINESE JOURNAL OF CHEMISTRY, 2019, 37 (11) :1125-1130
[43]   Mild and Selective Cobalt-Catalyzed Chemodivergent Transfer Hydrogenation of Nitriles [J].
Shao, Zhihui ;
Fu, Shaomin ;
Wei, Mufeng ;
Zhou, Shaolin ;
Liu, Qiang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (47) :14653-14657
[44]   ISOPRENE HYDROGENATION IN THE PRESENCE OF COBALT PHOSPHINE COMPLEXES [J].
SHMIDT, FK ;
LEVKOVSKII, YS ;
RYUTINA, NM ;
LIPOVICH, VG .
REACTION KINETICS AND CATALYSIS LETTERS, 1979, 12 (04) :475-478
[45]  
SIMANDI LI, 1970, ACTA CHIM HUNG, V64, P125
[46]   Unsymmetrical Iron P-NH-P′ Catalysts for the Asymmetric Pressure Hydrogenation of Aryl Ketones [J].
Smith, Samantha A. M. ;
Lagaditis, Paraskevi O. ;
Luepke, Anne ;
Lough, Alan J. ;
Morris, Robert H. .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (30) :7212-7216
[47]   Enantioselective Hydrogenation of Ketones Catalyzed by Chiral Cobalt Complexes Containing PNNP Ligand [J].
Zhang, Dong ;
Zhu, En-Ze ;
Lin, Zhi-Wei ;
Wei, Zan-Bin ;
Li, Yan-Yun ;
Gao, Jing-Xing .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (11) :1323-1326
[48]   Understanding the Mechanisms of Cobalt-Catalyzed Hydrogenation and Dehydrogenation Reactions [J].
Zhang, Guoqi ;
Vasudevan, Kalyan V. ;
Scott, Brian L. ;
Hanson, Susan K. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (23) :8668-8681
[49]   Mild and Homogeneous Cobalt-Catalyzed Hydrogenation of C=C, C=O, and C=N Bonds [J].
Zhang, Guoqi ;
Scott, Brian L. ;
Hanson, Susan K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (48) :12102-12106
[50]   Lutidine-Based Chiral Pincer Manganese Catalysts for Enantioselective Hydrogenation of Ketones [J].
Zhang, Linli ;
Tang, Yitian ;
Han, Zhaobin ;
Ding, Kuiling .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (15) :4973-4977