Palladium-catalyzed asymmetric hydrogenation of 3-phthalimido substituted quinolines

被引:69
作者
Cai, Xian-Feng [1 ]
Huang, Wen-Xue [1 ]
Chen, Zhang-Pei [1 ]
Zhou, Yong-Gui [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
基金
中国国家自然科学基金;
关键词
BRONSTED ACID; ENANTIOSELECTIVE SYNTHESIS; HETEROAROMATIC-COMPOUNDS; FACILE ACCESS; LIGANDS; QUINOXALINES; PHOSPHONATES; REDUCTION; IMINES; SCOPE;
D O I
10.1039/c4cc04386c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Homogeneous Pd-catalyzed asymmetric hydrogenation of 3-phthalimido substituted quinolines was successfully developed, providing facile access to chiral substituted tetrahydroquinolines bearing two contiguous stereogenic centers with up to 90% ee.
引用
收藏
页码:9588 / 9590
页数:3
相关论文
共 69 条
[1]   Pd-catalyzed asymmetric hydrogenation of α-fluorinated iminoesters in fluorinated alcohol:: A new and catalytic enantioselective synthesis of fluoro α-amino acid derivatives [J].
Abe, H ;
Amii, H ;
Uneyama, K .
ORGANIC LETTERS, 2001, 3 (03) :313-315
[2]   New chiral ligands bearing two N-heterocyclic carbene moieties at a dioxolane backbone. Gold, palladium and rhodium complexes as enantioselective catalysts [J].
Arnanz, Avelina ;
Gonzalez-Arellano, Camino ;
Juan, Alberto ;
Villaverde, Gonzalo ;
Corma, Avelino ;
Iglesias, Marta ;
Sanchez, Felix .
CHEMICAL COMMUNICATIONS, 2010, 46 (17) :3001-3003
[3]  
Barton D., 1999, Comprehensive natural products chemistry, V1st
[4]   Synthesis of Electron-Rich CNN-Pincer Complexes, with N-Heterocyclic Carbene and (S)-Proline Moieties and Application to Asymmetric Hydrogenation [J].
Boronat, Merce ;
Corma, Avelino ;
Gonzalez-Arellano, Camino ;
Iglesias, Marta ;
Sanchez, Felix .
ORGANOMETALLICS, 2010, 29 (01) :134-141
[5]   Synthesis of Chiral Exocyclic Amines by Asymmetric Hydrogenation of Aromatic Quinolin-3-amines [J].
Cai, Xian-Feng ;
Guo, Ran-Ning ;
Chen, Mu-Wang ;
Shi, Lei ;
Zhou, Yong-Gui .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (24) :7245-7248
[6]   Chiral Phosphoric Acid-Catalyzed Asymmetric Transfer Hydrogenation of Quinolin-3-amines [J].
Cai, Xian-Feng ;
Guo, Ran-Ning ;
Feng, Guang-Shou ;
Wu, Bo ;
Zhou, Yong-Gui .
ORGANIC LETTERS, 2014, 16 (10) :2680-2683
[7]  
Canty A. J., 2000, HIGHER OXIDATION STA
[8]   Palladium-Catalyzed Asymmetric Hydrogenation of α-Acyloxy-1-arylethanones [J].
Chen, Jianzhong ;
Liu, Delong ;
Butt, Nicholas ;
Li, Chao ;
Fan, Dongyang ;
Liu, Yangang ;
Zhang, Wanbin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (44) :11632-11636
[9]   Enantioselective Pd-Catalyzed Hydrogenation of Fluorinated Imines: Facile Access to Chiral Fluorinated Amines [J].
Chen, Mu-Wang ;
Duan, Ying ;
Chen, Qing-An ;
Wang, Duo-Sheng ;
Yu, Chang-Bin ;
Zhou, Yong-Gui .
ORGANIC LETTERS, 2010, 12 (21) :5075-5077
[10]   Homogeneous palladium-catalyzed asymmetric hydrogenation [J].
Chen, Qing-An ;
Ye, Zhi-Shi ;
Duan, Ying ;
Zhou, Yong-Gui .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (02) :497-511