Asymmetric transfer hydrogenation of aromatic ketones catalyzed by the iridium hydride complex under ambient conditions

被引:82
作者
Chen, JS [1 ]
Li, YY [1 ]
Dong, ZR [1 ]
Li, BZ [1 ]
Gao, JX [1 ]
机构
[1] Xiamen Univ, Dept Chem, State Key Lab Phys Chem Solid Surfaces, Xiamen 361005, Peoples R China
基金
中国国家自然科学基金;
关键词
iridium hydride complex; chiral ligand; aromatic ketone; asymmetric transfer hydrogenation;
D O I
10.1016/j.tetlet.2004.09.088
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chiral Ir catalytic system generated in situ from iridium hydride complex and chiral diaminodiphosphine ligand was employed in asymmetric transfer hydrogenation of aromatic ketones to give the corresponding optically active alcohols, with up to 99% ee in high yield were obtained even when the substrate-to-catalyst molar ratio reached 10000:1. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8415 / 8418
页数:4
相关论文
共 33 条
[1]  
Abad MM, 1999, CHEM COMMUN, P381
[2]   Isolation and crystal structure of a water-soluble iridium hydride: A robust and highly active catalyst for acid-catalyzed transfer hydrogenations of carbonyl compounds in acidic media [J].
Abura, T ;
Ogo, S ;
Watanabe, Y ;
Fukuzumi, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) :4149-4154
[3]   New chiral ruthenium(II) catalysts containing 2,6-bis(4′-(R)-phenyloxazolin-2′-yl)pyridine (Ph-pybox) ligands for highly enantioselective transfer hydrogenation of ketones [J].
Cuervo, D ;
Gamasa, MP ;
Gimeno, J .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (02) :425-432
[4]   ASYMMETRIC SYNTHESIS OF HYDRATROPIC ACID AND AMINO-ACIDS BY HOMOGENEOUS CATALYTIC HYDROGENATION [J].
DANG, TP ;
KAGAN, HB .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (10) :481-&
[5]   Dihydrogen complexes as homogeneous reduction catalysts [J].
Esteruelas, MA ;
Oro, LA .
CHEMICAL REVIEWS, 1998, 98 (02) :577-588
[6]   SYNTHESIS AND CHARACTERIZATION OF NEW HYDRIDOIRIDIUM COMPLEXES CONTAINING CARBOXYLATE LIGANDS [J].
ESTERUELAS, MA ;
GARCIA, MP ;
LAHOZ, FJ ;
MARTIN, M ;
MODREGO, J ;
ONATE, E ;
ORO, LA .
INORGANIC CHEMISTRY, 1994, 33 (16) :3473-3480
[7]   CHIRAL COPPER SEMICORRIN COMPLEXES AS ENANTIOSELECTIVE CATALYSTS FOR THE CYCLOPROPANATION OF OLEFINS BY DIAZO-COMPOUNDS [J].
FRITSCHI, H ;
LEUTENEGGER, U ;
PFALTZ, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (11) :1005-1006
[8]   Inter- and intramolecular activation of aromatic C-H bonds by diphosphine and hydrido-bridged dinuclear iridium complexes [J].
Fujita, K ;
Nakaguma, H ;
Hamada, T ;
Yamaguchi, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12368-12369
[9]   A ruthenium(II) complex with a C-2-symmetric diphosphine/diamine tetradentate ligand for asymmetric transfer hydrogenation of aromatic ketones [J].
Gao, JX ;
Ikariya, T ;
Noyori, R .
ORGANOMETALLICS, 1996, 15 (04) :1087-1089
[10]  
Gao JX, 2000, CHIRALITY, V12, P383, DOI 10.1002/(SICI)1520-636X(2000)12:5/6<383::AID-CHIR15>3.0.CO