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
[71]   Asymmetric Hydrogenation of Tetrasubstituted Cyclic Enones to Chiral Cycloalkanols with Three Contiguous Stereocenters [J].
Liu, Yun-Ting ;
Chen, Ji-Qang ;
Li, Lin-Ping ;
Shao, Xin-Yang ;
Xie, Jian-Hua ;
Zhou, Qi-Lin .
ORGANIC LETTERS, 2017, 19 (12) :3231-3234
[72]   Manganese-Catalyzed Hydrogenation of Amides and Polyurethanes: Is Catalyst Inhibition an Additional Barrier to the Efficient Hydrogenation of Amides and Their Derivatives? [J].
Luk, James ;
Oates, Conor L. ;
Garcia, Jose A. Fuentes ;
Clarke, Matthew L. ;
Kumar, Amit .
ORGANOMETALLICS, 2024, 43 (02) :85-93
[73]   Iridium-catalyzed chemoselective asymmetric hydrogenation of conjugated enones with ferrocene-based multidentate phosphine ligands [J].
Ma, Jinming ;
Li, Wendian ;
He, Lin ;
Lv, Hui .
CHEMICAL COMMUNICATIONS, 2022, 58 (39) :5841-5844
[74]   A New Phosphine-Amine-Oxazoline Ligand for Ru-Catalyzed Asymmetric Hydrogenation of N-Phosphinylimines [J].
Ma, Xiaochen ;
Qiao, Lin ;
Liu, Guixia ;
Huang, Zheng .
CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (12) :1151-1155
[75]   Recent Developments of Manganese Complexes for Catalytic Hydrogenation and Dehydrogenation Reactions [J].
Maji, Biplab ;
Barman, Milan K. .
SYNTHESIS-STUTTGART, 2017, 49 (15) :3377-3393
[76]   SYNTHESIS OF 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP), AN ATROPISOMERIC CHIRAL BIS(TRIARYL)PHOSPHINE, AND ITS USE IN THE RHODIUM(I)-CATALYZED ASYMMETRIC HYDROGENATION OF ALPHA-(ACYLAMINO)ACRYLIC ACIDS [J].
MIYASHITA, A ;
YASUDA, A ;
TAKAYA, H ;
TORIUMI, K ;
ITO, T ;
SOUCHI, T ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (27) :7932-7934
[77]   TRANSITION METAL-CARBON BONDS .42. COMPLEXES OF NICKEL, PALLADIUM, PLATINUM, RHODIUM AND IRIDIUM WITH TRIDENTATE LIGAND 2,6-BIS[(DI-T-BUTYLPHOSPHINO)METHYL]PHENYL [J].
MOULTON, CJ ;
SHAW, BL .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1976, (11) :1020-1024
[78]   Highly Enantioselective Hydrogenation of Non-ortho-Substituted 2-Pyridyl Aryl Ketones via Iridium-f-Diaphos Catalysis [J].
Nian, Sanfei ;
Ling, Fei ;
Chen, Jiachen ;
Wang, Ze ;
Shen, Haiwei ;
Yi, Xiao ;
Yang, Yun-Fang ;
She, Yuanbin ;
Zhong, Weihui .
ORGANIC LETTERS, 2019, 21 (14) :5392-5396
[79]   Asymmetric hydrogenation of aromatic ketones using an iridium(I) catalyst containing ferrocene-based P-N-N tridentate ligands [J].
Nie, Huifang ;
Zhou, Gang ;
Wang, Quanjun ;
Chen, Weiping ;
Zhang, Shengyong .
TETRAHEDRON-ASYMMETRY, 2013, 24 (24) :1567-1571
[80]   Transition-Metal-Catalyzed Enantioselective Propargylic Substitution Reactions of Propargylic Alcohol Derivatives with Nucleophiles [J].
Nishibayashi, Yoshiaki .
SYNTHESIS-STUTTGART, 2012, 44 (04) :489-503