Enantioselective hydrogenation of aromatic ketones catalyzed by Ru complexes of Goodwin-Lions-type sp2N/sp3N hybrid Ligands R-BINAN-R′-Py

被引:104
作者
Huang, Hanmin
Okuno, Tomoko
Tsuda, Kazuomi
Yoshimura, Masahiro
Kitamura, Masato [1 ]
机构
[1] Nagoya Univ, Res Ctr Mat Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Dept Chem, Chikusa Ku, Nagoya, Aichi 4648602, Japan
关键词
D O I
10.1021/ja062451a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Goodwin-Lions-type sp2N/sp3N hybrid ligands R-BINAN-R′-Py possessing a C2 axis binaphthyl skeleton have been designed and synthesized. Combination of the new non-phosphine ligand with Ru(π-CH2C(CH3)CH2)2(cod) has been revealed to catalyze the hydrogenation of aromatic ketones with high enantioselectivity of up to 99% ee. The reaction proceeds essentially without the need for any bases, but the reactivity is enhanced by the addition of KOt-C4H9 attaining an S/C ratio of up to 10000. The success should expand the range of possibilities in designing catalysts not only for hydrogenation but also for many other reactions. Copyright © 2006 American Chemical Society.
引用
收藏
页码:8716 / 8717
页数:2
相关论文
共 32 条
[11]   Origin of the minor enantiomeric product in a noyori asymmetric hydrogenation: Evidence for pathways different to the major mechanism [J].
Ishibashi, Y ;
Bessho, Y ;
Yoshimura, M ;
Tsukamoto, M ;
Kitamura, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) :7287-7290
[12]   Hydrogenation of aromatic ketones catalyzed by (η5-C5(CH3)5)Ru complexes bearing primary amines [J].
Ito, M ;
Hirakawa, M ;
Murata, K ;
Ikariya, T .
ORGANOMETALLICS, 2001, 20 (03) :379-381
[13]   New ruthenium catalysts containing chiral Schiff bases for the asymmetric hydrogenation of acetophenone [J].
Karamé, I ;
Jahjah, M ;
Messaoudi, A ;
Tommasino, ML ;
Lemaire, M .
TETRAHEDRON-ASYMMETRY, 2004, 15 (10) :1569-1581
[14]   Chiral zirconium complexes with bianiline-based N4-donor ligands [J].
Kettunen, M ;
Vedder, C ;
Schaper, F ;
Leskelä, M ;
Mutikainen, I ;
Brintzinger, HH .
ORGANOMETALLICS, 2004, 23 (16) :3800-3807
[15]   HOMOGENEOUS ASYMMETRIC HYDROGENATION OF FUNCTIONALIZED KETONES [J].
KITAMURA, M ;
OHKUMA, T ;
INOUE, S ;
SAYO, N ;
KUMOBAYASHI, H ;
AKUTAGAWA, S ;
OHTA, T ;
TAKAYA, H ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :629-631
[16]  
Kitamura M., 2004, RUTHENIUM ORGANIC SY, P3
[17]   Predetermination of chirality at octahedral centres with tetradentate ligands: prospects for enantioselective catalysis [J].
Knight, PD ;
Scott, P .
COORDINATION CHEMISTRY REVIEWS, 2003, 242 (1-2) :125-143
[18]  
Knof U, 1999, ANGEW CHEM INT EDIT, V38, P302, DOI 10.1002/(SICI)1521-3773(19990201)38:3<302::AID-ANIE302>3.0.CO
[19]  
2-G
[20]   ENANTIOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CARBONYL-COMPOUNDS - CHIRALITY TRANSFER, MULTIPLICATION, AND AMPLIFICATION [J].
NOYORI, R ;
KITAMURA, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (01) :49-69