Chiral P,N,N-Ligands for Asymmetric Hydrogenation

被引:9
作者
Liang, Ding-Hua [1 ]
Hou, Chuan-Jin [1 ]
Li, Qi [1 ]
Qin, Hao [1 ]
Li, Ling [1 ]
Hu, Xiang-Ping [2 ]
机构
[1] Dalian Polytech Univ, Sch Light Ind & Chem Engn, Dalian 116034, Peoples R China
[2] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
关键词
Asymmetric catalysis; Chiral ligands; Hydrogenation; P; N; N-ligands; LIGAND BIFUNCTIONAL CATALYSIS; BETA-KETO-ESTERS; ENANTIOSELECTIVE HYDROGENATION; TRIDENTATE LIGANDS; IRIDIUM CATALYSTS; 1,2-AMINO ALCOHOLS; EFFICIENT ACCESS; GROUP LEADS; COMPLEXES; MECHANISM;
D O I
10.1002/adsc.202400092
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The chiral P,N,N-ligands represented a new type of tridentate ligand developed in recent years and displayed wide utilities in asymmetric catalysis. In the past decades, numerous chiral P,N,N-ligands with ferrocene, phenethylamine and spiro backbones were synthesized by addition of an aminopyridine, imidazole or diamines coordinating group. These chiral tridentate P,N,N-ligands showed excellent performance in the ruthenium, iridium, manganese, or cobalt-catalyzed asymmetric hydrogenations. A wide range of substrates, including simple ketones, alpha-halogenated ketones, alpha-hydroxy ketones, alpha- or beta-amino keto- ones, alpha-, gamma-, or delta-keto acids, alpha- or beta-keto amides, beta- or delta-keto esters, alpha- or beta-enones, olefins, imines, quinolines and indoles, could be hydrogenated to afford the corresponding chiral products with high yields and enantioselectivities. In this review, progress on the asymmetric hydrogenation of C=O, C=N, C=C bonds with chiral tridentate P,N,N-ligands was summarized. image
引用
收藏
页码:2165 / 2185
页数:21
相关论文
共 161 条
[91]   Ir-catalyzed asymmetric hydrogenation of simple ketones with chiral ferrocenyl P,N,N-ligands [J].
Qin, Chao ;
Hou, Chuan-Jin ;
Liu, Hongzhu ;
Liu, Yan-Jun ;
Huang, De-Zhi ;
Hu, Xiang-Ping .
TETRAHEDRON LETTERS, 2018, 59 (08) :719-722
[92]   Mechanism of asymmetric hydrogenation of ketones catalyzed by BINAP/1,2-diamine-ruthenium(II) complexes [J].
Sandoval, CA ;
Ohkuma, T ;
Muñiz, K ;
Noyori, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (44) :13490-13503
[93]   Practical Access to Key Intermediates of Crizotinib, Lorlatinib, and Pibrentasvir Enabled by Oxa-Spirocyclic Ligands [J].
Song, Jingyuan ;
Zhao, Menglong ;
Xiao, Renwei ;
Chen, Gen-Qiang ;
Zhang, Xumu .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2023, 27 (12) :2280-2285
[94]   Highly efficient and enantioselective synthesis of chiral lactones via Ir-catalysed asymmetric hydrogenation of ketoesters [J].
Song, Jingyuan ;
Yin, Congcong ;
Zhang, Yao ;
Shi, Yongjie ;
Li, Yingjun ;
Chen, Gen-Qiang ;
Zhang, Xumu .
CHEMICAL COMMUNICATIONS, 2022, 58 (60) :8408-8411
[95]   Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)-H Bonds [J].
Su, Xiao-Long ;
Ye, Liu ;
Chen, Ji-Jun ;
Liu, Xiao-Dong ;
Jiang, Sheng-Peng ;
Wang, Fu-Li ;
Liu, Lin ;
Yang, Chang-Jiang ;
Chang, Xiao-Yong ;
Li, Zhong-Liang ;
Gu, Qiang-Shuai ;
Liu, Xin-Yuan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (01) :380-384
[96]   Regio- and Enantioselective Allylic Cyanomethylation by Synergistic Rhodium and Silane Catalysis [J].
Sun, Minghe ;
Wei, Linsheng ;
Li, Changkun .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (07) :3897-3902
[97]   New chiral phosphorus ligands for enantioselective hydrogenation [J].
Tang, WJ ;
Zhang, XM .
CHEMICAL REVIEWS, 2003, 103 (08) :3029-3069
[98]   Highly Enantioselective Iridium-Catalyzed Hydrogenation of o-Amidophenyl Ketones Enabled by 1,2-Diphenylethylenediamine- Derived P,N,N-Ligands with Tertiary Amine Terminus [J].
Wan, Yin-Bo ;
Hu, Xiang-Ping .
ORGANIC LETTERS, 2022, 24 (31) :5797-5801
[99]   Chiral Tridentate Ligands in Transition Metal-Catalyzed Asymmetric Hydrogenation [J].
Wang, Heng ;
Wen, Jialin ;
Zhang, Xumu .
CHEMICAL REVIEWS, 2021, 121 (13) :7530-7567
[100]   Design of Hemilabile N,N,N-Ligands in Copper-Catalyzed Enantioconvergent Radical Cross-Coupling of Benzyl/Propargyl Halides with Alkenylboronate Esters [J].
Wang, Peng-Fei ;
Yu, Jiao ;
Guo, Kai-Xin ;
Jiang, Sheng-Peng ;
Chen, Ji-Jun ;
Gu, Qiang-Shuai ;
Liu, Ji-Ren ;
Hong, Xin ;
Li, Zhong-Liang ;
Liu, Xin-Yuan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (14) :6442-6452