Asymmetric Hydrogenation of Polysubstituted Isoquinolines with Chiral Boranes

被引:0
作者
Zou, Fuqu [1 ,2 ]
Feng, Xiangqing [1 ,2 ]
Du, Haifeng [1 ,2 ]
机构
[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金
国家重点研发计划; 中国国家自然科学基金;
关键词
FRUSTRATED LEWIS PAIRS; IRIDIUM-CATALYZED HYDROGENATION; METAL-FREE HYDROGENATIONS; ENANTIOSELECTIVE HYDROGENATION; CHEMISTRY; HETEROCYCLES; QUINOLINES; PROGRESS; BEARING; ROUTE;
D O I
10.1021/acs.orglett.5c00272
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper describes an asymmetric hydrogenation of 1,3-disubstituted isoquinolines catalyzed by chiral borane derived from chiral alkene, giving the desired cis-products in high yields with up to 96% ee. In particular, the asymmetric hydrogenation of challenging 1,3,4-trisubstituted isoquinolines could proceed smoothly to afford the corresponding products in high yields with moderate ee's for the first time.
引用
收藏
页码:2186 / 2190
页数:5
相关论文
共 50 条
[21]   Asymmetric Hydrogenation of 2-Aryl-5,6-dihydropyrazine Derivatives with Chiral Cationic Ruthenium Diamine Catalysts [J].
Li, Yong ;
He, Yanmei ;
Chen, Fei ;
Fan, Qinghua .
CHINESE JOURNAL OF CHEMISTRY, 2014, 32 (10) :991-994
[22]   Utilization of optically active secondary phosphine-boranes: synthesis of P-chiral diphosphines and their enantioinduction ability in rhodium-catalyzed asymmetric hydrogenation [J].
Imamoto, Tsuneo ;
Horiuchi, Yumi ;
Hamanishi, Eri ;
Takeshita, Satoshi ;
Tamura, Ken ;
Sugiya, Masashi ;
Yoshida, Kazuhiro .
TETRAHEDRON, 2015, 71 (37) :6471-6480
[23]   Exploration of chiral diastereomeric spiroketal (SPIROL)-based phosphinite ligands in asymmetric hydrogenation of heterocycles [J].
Sun, Siyuan ;
Nagorny, Pavel .
CHEMICAL COMMUNICATIONS, 2020, 56 (60) :8432-8435
[24]   Asymmetric Hydrogenation of Heteroarenes with Multiple Heteroatoms [J].
Chen, Zhang-Pei ;
Zhou, Yong-Gui .
SYNTHESIS-STUTTGART, 2016, 48 (12) :1769-1781
[25]   Chiral P,N,N-Ligands for Asymmetric Hydrogenation [J].
Liang, Ding-Hua ;
Hou, Chuan-Jin ;
Li, Qi ;
Qin, Hao ;
Li, Ling ;
Hu, Xiang-Ping .
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (10) :2165-2185
[26]   New chiral diphosphoramidite rhodium(I) complexes for asymmetric hydrogenation [J].
Drommi, Dario ;
Micalizzi, Giuseppe ;
Arena, Carmela Grazia .
APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (08) :614-619
[27]   Chiral (Cyclopentadienone)iron Complexes for the Catalytic Asymmetric Hydrogenation of Ketones [J].
Gajewski, Piotr ;
Renom-Carrasco, Marc ;
Facchini, Sofia Vailati ;
Pignataro, Luca ;
Lefort, Laurent ;
de Vries, Johannes G. ;
Ferraccioli, Raffaella ;
Forni, Alessandra ;
Piarulli, Umberto ;
Gennari, Cesare .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (09) :1887-1893
[28]   The application of the chiral ligand DTBM-SegPHOS in asymmetric hydrogenation [J].
Chen, Jianzhong ;
Butt, Nicholas A. ;
Zhang, Wanbin .
RESEARCH ON CHEMICAL INTERMEDIATES, 2019, 45 (12) :5959-5974
[29]   Cycloiridated Helicenes as Chiral Catalysts in the Asymmetric Transfer Hydrogenation of Imines [J].
Sakamoto, Daisuke ;
Sanchez, Isabel Gay ;
Rybacek, Jiri ;
Vacek, Jaroslav ;
Bednarova, Lucie ;
Pazderkova, Marketa ;
Pohl, Radek ;
Cisarova, Ivana ;
Stara, Irena G. ;
Stary, Ivo .
ACS CATALYSIS, 2022, 12 (17) :10793-10800
[30]   Stereocontrol via Propeller Chirality in FLP-Catalyzed Asymmetric Hydrogenation [J].
Kotai, B. ;
Laczko, G. ;
Hamza, A. ;
Papai, I. .
CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (21)