Enantioselective Hydrogenation of N-H Imines

被引:146
作者
Hou, Guohua [3 ]
Gosselin, Francis [1 ,2 ]
Li, Wei [3 ]
McWilliams, Christopher [1 ]
Sun, Yongkui [1 ]
Weisel, Mark [1 ]
O'Shea, Paul D. [2 ]
Chen, Cheng-yi [1 ]
Davies, Ian W. [1 ]
Zhang, Xumu [3 ]
机构
[1] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA
[2] Merck Frosst Ctr Therapeut Res, Dept Proc Res, Kirkland, PQ H9H 3L1, Canada
[3] Rutgers State Univ, Dept Chem, Piscataway, NJ 08854 USA
基金
美国国家卫生研究院;
关键词
CATALYZED ASYMMETRIC HYDROGENATION; CHIRAL TITANOCENE CATALYST; ACYCLIC IMINES; EFFICIENT SYNTHESIS; LIGANDS; ENAMINES; COMPLEXES; TOSYLIMINES; DERIVATIVES; RHODIUM(I);
D O I
10.1021/ja903319r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N-H ketoimines 3a-3v are readily prepared in high yield via organometallic addition to nitrites and isolated as corresponding bench-stable hydrochloride salts. Homogeneous asymmetric hydrogenation of unprotected N-H ketoimines 3a-3v using Ir-(S,S)-f binaphane as catalyst provides chiral amines 4a-4v in 90-95% yield with enantioselectivities up to 95% ee.
引用
收藏
页码:9882 / +
页数:3
相关论文
共 35 条
[1]  
[Anonymous], 2007, The Handbook of Homogeneous Hydrogenation
[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 N-tosylimines catalyzed by BINAP-ruthenium(II) complexes [J].
Charette, AB ;
Giroux, A .
TETRAHEDRON LETTERS, 1996, 37 (37) :6669-6672
[4]   An efficient synthesis of N-unsubstituted imines as organoborane adducts stable at room temperature:: New promising intermediates for synthesis [J].
Chen, GM ;
Brown, HC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4217-4218
[5]   Enantioselective hydrogenation of imines using a diverse library of ruthenium dichloride(diphospbine)(diamine) precatalysts [J].
Cobley, CJ ;
Henschke, JP .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :195-201
[6]   Unprecedented catalytic asymmetric reduction of N-H imines [J].
Gosselin, F ;
O'Shea, PD ;
Roy, S ;
Reamer, RA ;
Chen, CY ;
Volante, RP .
ORGANIC LETTERS, 2005, 7 (02) :355-358
[7]   Highly efficient Rh(I)-catalyzed asymmetric hydrogenation of enamines using monodente spiro phosphonite ligands [J].
Hou, Guo-Hua ;
Xie, Jian-Hua ;
Wang, Li-Xin ;
Zhou, Qi-Lin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (36) :11774-11775
[8]   Iridium-Catalyzed Asymmetric Hydrogenation of Cyclic Enamines [J].
Hou, Guo-Hua ;
Xie, Jian-Hua ;
Yan, Pu-Cha ;
Zhou, Qi-Lin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (04) :1366-+
[9]   Highly efficient synthesis of β-amino acid derivatives via asymmetric hydrogenation of unprotected enamines [J].
Hsiao, Y ;
Rivera, NR ;
Rosner, T ;
Krska, SW ;
Njolito, E ;
Wang, F ;
Sun, YK ;
Armstrong, JD ;
Grabowski, EJJ ;
Tillyer, RD ;
Spindler, F ;
Malan, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (32) :9918-9919
[10]   Enantioselective hydrogenation of acyclic aromatic N-aryl imines catalyzed by an iridium complex of (S,S)-1,2-bis(tert-butylmethylphosphino)ethane [J].
Imamoto, Tsuneo ;
Iwadate, Noriyuki ;
Yoshida, Kazuhiro .
ORGANIC LETTERS, 2006, 8 (11) :2289-2292