Air-Stable and Phosphine-Free Iridium Catalysts for Highly Enantioselective Hydrogenation of Quinoline Derivatives

被引:134
作者
Li, Zhi-Wei [1 ]
Wang, Tian-Li [1 ]
He, Yan-Mei [1 ]
Wang, Zhi-Jian [1 ]
Fan, Qing-Hua [1 ]
Pan, Jie [1 ]
Xu, Li-Jun [2 ]
机构
[1] Chinese Acad Sci, Ctr Chem Biol, Inst Chem, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
[2] Renmin Univ China, Dept Chem, Beijing 100972, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1021/ol802016w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantioselective hydrogenation of quinoline derivatives catalyzed by phosphine-free chiral cationic Cp*Ir(OTf)(CF3TsDPEN) complex (CF3TsDPEN = N-(p-trifluoromethylbenzenesulfonyl)-1,2-diphenylethylene-diamine) afforded the 1,2,3,4-tetrahydroquinoline derivatives in up to 99% ee. The reaction could be carried out with a substrate-to-catalyst molar ratio as high as 1000 in undegassed methanol and with no need for inert gas protection.
引用
收藏
页码:5265 / 5268
页数:4
相关论文
共 40 条
[1]   Aerobic oxidative kinetic resolution of racemic secondary alcohols with chiral bifunctional amido complexes [J].
Arita, Sachiko ;
Koike, Takashi ;
Kayaki, Yoshihito ;
Ikariya, Takao .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (13) :2447-2449
[2]   Selective hydrogenation for fine chemicals: Recent trends and new developments [J].
Blaser, HU ;
Malan, C ;
Pugin, B ;
Spindler, F ;
Steiner, H ;
Studer, M .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :103-151
[3]   Asymmetric hydrogenation of quinolines with recyclable and air-stable iridium catalyst systems [J].
Chan, Sau Hing ;
Lam, Kim Hung ;
Li, Yue-Ming ;
Xu, Lijin ;
Tang, Weijun ;
Lam, Fuk Loi ;
Lo, Wai Hung ;
Yu, Wing Yiu ;
Fan, Qinghua ;
Chan, Albert S. C. .
TETRAHEDRON-ASYMMETRY, 2007, 18 (22) :2625-2631
[4]   Nitrogen-containing ligands for asymmetric homogeneous and heterogeneous catalysis [J].
Fache, F ;
Schulz, E ;
Tommasino, ML ;
Lemaire, M .
CHEMICAL REVIEWS, 2000, 100 (06) :2159-2231
[5]   Asymmetric hydrogenation of aromatic compounds [J].
Glorius, F .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (23) :4171-4175
[6]   Ruthenium-catalyzed ionic hydrogenation of iminium cations. Scope and mechanism [J].
Guan, HR ;
Iimura, M ;
Magee, MP ;
Norton, JR ;
Zhu, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7805-7814
[7]   The development of double axially chiral phosphoric acids and their catalytic transfer hydrogenation of quinolines [J].
Guo, Qun-Sheng ;
Du, Da-Ming ;
Xu, Jiaxi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (04) :759-762
[8]   Mechanistic insights into the phosphine-free RuCp☆-diamine-catalyzed hydrogenation of aryl ketones:: Experimental and theoretical evidence for an alcohol-mediated dihydrogen activation [J].
Hedberg, C ;
Källström, K ;
Arvidsson, PI ;
Brandt, P ;
Andersson, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (43) :15083-15090
[9]   Homogeneous catalytic reduction of dioxygen using transfer hydrogenation catalysts [J].
Heiden, Zachariah M. ;
Rauchfuss, Thomas B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) :14303-14310
[10]   Enantioselective hydrogenation of aromatic ketones catalyzed by Ru complexes of Goodwin-Lions-type sp2N/sp3N hybrid Ligands R-BINAN-R′-Py [J].
Huang, Hanmin ;
Okuno, Tomoko ;
Tsuda, Kazuomi ;
Yoshimura, Masahiro ;
Kitamura, Masato .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (27) :8716-8717