Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by RuCl2[(S)-P-Phos]-[(S)-DAIPEN]

被引：2

作者：

Jiang He ^{[1
]}

Wang Jin-Bo ^{[1
]}

Xiong Wei ^{[1
]}

Jia Yun ^{[1
]}

Qin Rui-Xiang ^{[1
]}

Liu De-Rong ^{[1
]}

Chen Hua ^{[2
]}

机构：

[1] Chongqing Univ Sci & Technol, Coll Chem & Chem Engn, Chongqing 401331, Peoples R China

[2] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

ACTA PHYSICO-CHIMICA SINICA | 2010年 / 26卷 / 03期

关键词：

Asymmetric hydrogenation; Ruthenium-phosphine complex; Chiral diamine; Aromatic ketones; BIARYL DIPHOSPHINE LIGAND; ENANTIOSELECTIVE HYDROGENATION; EFFICIENT; COMPLEXES;

D O I：

10.3866/PKU.WHXB20100225

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：

A ruthenium phosphine diamine complex RuCl2[(S)-P-Phos]-[(S)-DAIPEN] [P-Phos: 2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine, DAIPEN: 1,1'-di(4-anisyl)-2-iopropyl-1,2-ethylenediamine] for the asymmetric hydrogenation of aromatic ketones has been Studied. The influences of different bases. (CH3)(3)COK concentration, organic solvent, and molar ratio of substrate to catalyst on activity and enantioselectivity were investigated. Under the following optimum conditions: n(ketone):n(KOH):n(catalyst)=1000:20:1, p(H2)=2 MPa and T=30 degrees C the conversion of acetophenone and the enantioselectivity (ee) of S-1-phenylethanol was 100% and 88.5%, respectively. Additionally, the ee value of 2'-bromophenyl ethanol was 97.1%.

引用

页码：675 / 678

页数：4

共 21 条

[1] A catalyst for efficient and highly enantioselective hydrogenation of aromatic, heteroaromatic, and α,β-unsaturated ketones
Burk, MJ
Hems, W
Herzberg, D
Malan, C
Zanotti-Gerosa, A
[J]. ORGANIC LETTERS, 2000, 2 (26) : 4173 - 4176
[2] Ru-BICP-catalyzed asymmetric hydrogenation of aromatic ketones
Cao, P
Zhang, XM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06): : 2127 - 2129
[3] Asymmetric hydrogenation of ketones with ruthenium complexes of rac- and enantiopure (S,S)-1,2-bis((diphenylphosphino)methyl)cyclohexane:: A comparative study with rac- and (R)-BINAP
Doherty, Simon
Knight, Julian G.
Bell, Adam L.
Harrington, Ross W.
Clegg, William
[J]. ORGANOMETALLICS, 2007, 26 (09) : 2465 - 2468
[4] GABRICLA AG, 2005, ORG LETT, V7, P1449
[5] GABRICLA AG, 2006, J ORGANOMET CHEM, V691, P2332
[6] Hartmann R, 2001, ANGEW CHEM INT EDIT, V40, P3581, DOI 10.1002/1521-3773(20011001)40:19<3581::AID-ANIE3581>3.0.CO
[7] 2-7
[8] A concise synthesis of a new xylyl-biaryl diphosphine ligand for asymmetric hydrogenation of ketones
Henschke, JP
Zanotti-Gerosa, A
Moran, P
Harrison, P
Mullen, B
Casy, G
Lennon, IC
[J]. TETRAHEDRON LETTERS, 2003, 44 (23) : 4379 - 4383
[9] Synthesis and applications of HexaPHEMP, a novel biaryl diphosphine ligand
Henschke, JP
Burk, MJ
Malan, CG
Herzberg, D
Peterson, JA
Wildsmith, AJ
Cobley, CJ
Casy, G
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) : 300 - 307
[10] New ruthenium catalysts containing chiral Schiff bases for the asymmetric hydrogenation of acetophenone
Karamé, I
Jahjah, M
Messaoudi, A
Tommasino, ML
Lemaire, M
[J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (10) : 1569 - 1581

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