Iridium-Monodentate Phosphoramidite-Catalyzed Asymmetric Hydrogenation of Substituted Benzophenone N-H Imines

被引:100
作者
Hou, Guohua [1 ]
Tao, Ran [2 ]
Sun, Yongkui [2 ]
Zhang, Xumu [1 ]
Gosselin, Francis [2 ]
机构
[1] Rutgers State Univ, Dept Chem, Piscataway, NJ 08854 USA
[2] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA
基金
美国国家卫生研究院;
关键词
ENANTIOSELECTIVE HYDROGENATION; ARYLBORONIC ACIDS; ARYL KETONES; ARYLATION; DIARYLMETHYLAMINES; LIGANDS; TOSYLARYLIMINES; CETIRIZINE; REAGENTS; ALDIMINES;
D O I
10.1021/ja909583s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Homogeneous asymmetric hydrogenation of unprotected benzophenone N-H imines 1a-r using 1r-benzyl-N-methyl-MonoPhos as a catalyst provides chiral amines 2a-r in 80-96% yield with enantioselectivities up to 98% ee (18 examples) for ortho-substituted substrates.
引用
收藏
页码:2124 / +
页数:3
相关论文
共 45 条
[1]  
[Anonymous], 2007, The Handbook of Homogeneous Hydrogenation
[2]  
BAKER RK, 2007, Patent No. 2007062193
[3]   AN EFFICIENT SYNTHESIS OF THE BENZHYDRYLPIPERAZINE DELTA-OPIOID AGONIST (+)-BW373U86 [J].
BISHOP, MJ ;
MCNUTT, RW .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (12) :1311-1314
[4]   A room-temperature protocol for the rhodium(I)-catalyzed addition of arylboron compounds to sulfinimines [J].
Bolshan, Y ;
Batey, RA .
ORGANIC LETTERS, 2005, 7 (08) :1481-1484
[5]   Enantioselective addition of aryllithium reagents to aromatic imines mediated by 1,2-diamine ligands [J].
Cabello, N ;
Kizirian, JC ;
Alexakis, A .
TETRAHEDRON LETTERS, 2004, 45 (24) :4639-4642
[6]   Highly enantioselective hydrogenation of aromatic-heteroaromatic ketones [J].
Chen, CY ;
Reamer, RA ;
Chilenski, JR ;
McWilliams, CJ .
ORGANIC LETTERS, 2003, 5 (26) :5039-5042
[7]   Substituted diarylmethylamines by stereospecific intramolecular electrophilic arylation of lithiated ureas [J].
Clayden, Jonathan ;
Dufour, Jeremy ;
Grainger, Damian M. ;
Helliwell, Madeleine .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7488-+
[8]   Catalytic enantioselective synthesis of the second generation histamine antagonist cetirizine hydrochloride [J].
Corey, EJ ;
Helal, CJ .
TETRAHEDRON LETTERS, 1996, 37 (28) :4837-4840
[9]  
Cuss FM, [No title captured], Patent No. 0107050
[10]   Asymmetric synthesis of diarylmethylamines: preparation of selective opioid delta receptor ligands [J].
Delorme, D ;
Berthelette, C ;
Lavoie, R ;
Roberts, E .
TETRAHEDRON-ASYMMETRY, 1998, 9 (22) :3963-3966