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
[1]   Catalytic cycle for the asymmetric hydrogenation of prochiral ketones to chiral alcohols:: Direct hydride and proton transfer from chiral catalysts trans-Ru(H)2(diphosphine)(diamine) to ketones and direct addition of dihydrogen to the resulting hydridoamido complexes [J].
Abdur-Rashid, K ;
Faatz, M ;
Lough, AJ ;
Morris, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) :7473-7474
[2]   Development of Chiral Spiro P-N-S Ligands for Iridium-Catalyzed Asymmetric Hydrogenation of -Alkyl--Ketoesters [J].
Bao, Deng-Hui ;
Wu, Hui-Ling ;
Liu, Chao-Lun ;
Xie, Jian-Hua ;
Zhou, Qi-Lin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (30) :8791-8794
[3]   Asymmetric hydrogenation of exocyclic γ,δ-unsaturated β-ketoesters to functionalized chiral allylic alcohols via dynamic kinetic resolution [J].
Bin, Huai-Yu ;
Cheng, Li ;
Wu, Xiong ;
Zhu, Chang-Liang ;
Yang, Xiao-Hui ;
Xie, Jian-Hua ;
Zhou, Qi-Lin .
CHEMICAL SCIENCE, 2021, 12 (22) :7793-7799
[4]   Scalable Enantioselective Total Synthesis of (-)-Goniomitine [J].
Bin, Huai-Yu ;
Wang, Ke ;
Yang, Dan ;
Yang, Xiao-Hui ;
Xie, Jian-Hua ;
Zhou, Qi-Lin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (04) :1174-1177
[5]   Asymmetric catalysis. Part 149. Synthesis of new chiral tridentate ligands for enantioselective catalysis [J].
Brunner, H ;
Zettler, C ;
Zabel, M .
MONATSHEFTE FUR CHEMIE, 2003, 134 (09) :1253-1269
[6]   Stereodiverse Iterative Synthesis of 1,3-Polyol Arrays through Asymmetric Catalytic Hydrogenation. Formal Total Synthesis of (-)-Cyanolide A [J].
Che, Wen ;
Li, Yu-Zhen ;
Liu, Jin-Chi ;
Zhu, Shou-Fei ;
Xie, Jian-Hua ;
Zhou, Qi-Lin .
ORGANIC LETTERS, 2019, 21 (07) :2369-2373
[7]   Design and Synthesis of Chiral oxa-Spirocyclic Ligands for Ir-Catalyzed Direct Asymmetric Reduction of Bringmann's Lactones with Molecular H2 [J].
Chen, Gen-Qian ;
Lin, Bi-Jin ;
Huang, Jia-Ming ;
Zhao, Ling-Yu ;
Chen, Qi-Shu ;
Jia, Shi-Peng ;
Yin, Qin ;
Zhang, Xumu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (26) :8064-8068
[8]   The Ir-Catalyzed Asymmetric Hydrogenation of α-Halogenated Ketones Utilizing Cinchona-Alkaloid-Derived NNP Ligand to Produce (R)- and (S)-Halohydrins [J].
Chen, Qian ;
Sun, Hao ;
Li, Linlin ;
Tian, Jie ;
Xu, Qian ;
Ma, Nana ;
Li, Li ;
Zhang, Lin ;
Li, Chun .
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (23) :15986-15997
[9]   Ir-catalyzed asymmetric hydrogenation of β-keto esters with chiral ferrocenyl P, N, N-ligands [J].
Chen, Xiu-Shuai ;
Hou, Chuan-Jin ;
Qin, Chao ;
Liu, Hongzhu ;
Liu, Yan-Jun ;
Huang, De-Zhi ;
Hu, Xiang-Ping .
RSC ADVANCES, 2017, 7 (21) :12871-12875
[10]   A Counterion/Ligand-Tuned Chemo- and Enantioselective Copper- Catalyzed Intermolecular Radical 1,2-Carboamination of Alkenes [J].
Cheng, Xian-Yan ;
Zhang, Yu-Feng ;
Wang, Jia-Huan ;
Gu, Qiang-Shuai ;
Li, Zhong-Liang ;
Liu, Xin-Yuan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (39) :18081-18089