A new efficient chiral iridium catalyst for asymmetric transfer hydrogenation of ketones

被引：37

作者：

Li, YY ^{[1
]}

Zhang, H ^{[1
]}

Chen, JS ^{[1
]}

Liao, XL ^{[1
]}

Dong, ZR ^{[1
]}

Gao, JX ^{[1
]}

机构：

[1] Xiamen Univ, Dept Chem, State Key Lab Phys Chem Solid Surface, Xiamen 361005, Peoples R China

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2004年 / 218卷 / 02期

关键词：

chiral ligand; chiral iridium complex; asymmetric transfer hydrogenation; aromatic ketone; chiral alcohol;

D O I：

10.1016/j.molcata.2004.04.020

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The interaction of [Ir(COD)Cl](2) with chiral tetradentate diaminodiphosphine ligands gave chiral diaminodiphosphine-Ir(I) complexes, which were characterized by IR, NMR and CD. The new chiral iridium(l) complex catalysts were applied to asymmetric transfer hydrogenation of various aromatic ketones using 2-propanol as a source of hydrogen. The results showed that the corresponding chiral alcohols could be obtained with high activity (up to 99.4% yield) and excellent enantioselectivities (up to 99.0% ee) under mild conditions. Propiophenone was a preferred substrate with respect to catalytic activity and enantioselectivity in the presence of base. The catalytic turnover reached 4780 mol product/mol iridium and the turnover frequency was as high as 1593 h(-1) at 55degreesC. (C) 2004 Elsevier B.V. All rights reserved.

引用

页码：153 / 156

页数：4

共 25 条

[1] Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture [J].

Fujii, A ;

Hashiguchi, S ;

Uematsu, N ;

Ikariya, T ;

Noyori, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2521-2522

[2] ASYMMETRIC CATALYTIC REDUCTION OF CARBONYL-COMPOUNDS USING C-2 SYMMETRICAL DIAMINES AS CHIRAL LIGANDS [J].

GAMEZ, P ;

FACHE, F ;

LEMAIRE, M .

TETRAHEDRON-ASYMMETRY, 1995, 6 (03) :705-718

[3] Asymmetric transfer hydrogenation of prochiral ketones catalyzed by chiral ruthenium complexes with aminophosphine ligands [J].

Gao, JX ;

Xu, PP ;

Yi, XD ;

Yang, CB ;

Zhang, H ;

Cheng, SH ;

Wan, HL ;

Tsai, KR ;

Ikariya, T .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 147 (1-2) :105-111

[4] Cationic rhodium complexes with chiral tetradentate ligands as catalysts for enantioselective reduction of simple ketones [J].

Gao, JX ;

Yi, XD ;

Xu, PP ;

Tang, CL ;

Zhang, H ;

Wan, HL ;

Ikariya, T .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2000, 159 (01) :3-9

[5] 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

[6] The catalyst precursor, catalyst, and intermediate in the Ru-II-promoted asymmetric hydrogen transfer between alcohols and ketones [J].

Haack, KJ ;

Hashiguchi, S ;

Fujii, A ;

Ikariya, T ;

Noyori, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (03) :285-288

[7]

HALLE R, 1997, TETRAHEDRON-ASYMMETR, V8, P2101

[8] Synthesis of (1R,1R')-2,6-bis[1-(diphenylphosphino)ethyl]pyridine and its application in asymmetric transfer hydrogenation [J].

Jiang, QZ ;

VanPlew, D ;

Murtuza, S ;

Zhang, XM .

TETRAHEDRON LETTERS, 1996, 37 (06) :797-800

[9] Highly effective NPN-type tridentate ligands for asymmetric transfer hydrogenation of ketones [J].

Jiang, YT ;

Jiang, QZ ;

Zhu, GX ;

Zhang, XM .

TETRAHEDRON LETTERS, 1997, 38 (02) :215-218

[10] A new chiral bis(oxazolinlymethyl)amine ligand for Ru-catalyzed asymmetric transfer hydrogenation of ketones [J].

Jiang, YT ;

Jiang, QZ ;

Zhang, XM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3817-3818

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