Ruthenium(II)-assisted asymmetric hydrogen transfer reduction of acetophenone using chiral tridentate phosphorus-containing ligands derived from (1R, 2R)-1,2-diaminocyclohexane

被引:18
作者
Flores-López, CZ [1 ]
Flores-López, LZ [1 ]
Aguirre, G [1 ]
Hellberg, LH [1 ]
Parra-Hake, M [1 ]
Somanathan, R [1 ]
机构
[1] Inst Tecnol Tijuana, Ctr Grad & Invest, Tijuana 22000, BC, Mexico
关键词
asymmetric; Ruthenium(II); transfer; hydrogenation; Schiff base;
D O I
10.1016/j.molcata.2004.01.013
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
Several chiral and unsymmetrical tridentate [NNP]-type ligands with sp(2)-N and sp(3)-N were synthesized from monosulfonamide of (1R, 2R)-1,2-diaminocyclohexane and 2-(diphenylphosphino)benzaldehyde. Their ruthenium(II) complexes have been used in the enantioselective asymmetric hydrogen transfer reduction of acetophenone in 2-propanol with selectivities in the range 14-99% e.e. The good enantioselectivity with the ligands with sp(2)-N and sp(3)-N is believed to be due to formation of hexacoordinated complexes with a 2:1 ligand to metal ratio. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:73 / 79
页数:7
相关论文
共 44 条
[21]   New hybrid ligands with a trans-1,2-diaminocyclohexane backbone:: Competing chelation modes in palladium-catalyzed enantioselective allylic alkylation [J].
Kim, YK ;
Lee, SJ ;
Ahn, KH .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7807-7813
[22]   Catalytic enantioselective addition to imines [J].
Kobayashi, S ;
Ishitani, H .
CHEMICAL REVIEWS, 1999, 99 (05) :1069-1094
[23]   Ruthenium catalyzed asymmetric transfer hydrogenation based on chiral P,N,O Schiff base ligands and crystal structure of a ruthenium(II) complex bearing chiral P,N,O Schiff base ligands [J].
Kwong, HL ;
Lee, WS ;
Lai, TS ;
Wong, WT .
INORGANIC CHEMISTRY COMMUNICATIONS, 1999, 2 (02) :66-69
[24]  
Laue S, 2001, ADV SYNTH CATAL, V343, P711
[25]   Unsymmetric chiral Salen Schiff bases: A new chiral ligand pool from bis-Schiff bases containing two different salicylaldehyde units [J].
Lopez, J ;
Liang, S ;
Bu, XR .
TETRAHEDRON LETTERS, 1998, 39 (24) :4199-4202
[26]   Novel unsymmetric chiral Schiff bases possessing two different donor moieties: unique tetradentate ligands from combination of salicylaldehyde and acetylacetone units [J].
Lopez, J ;
Mintz, EA ;
Hsu, FL ;
Bu, XR .
TETRAHEDRON-ASYMMETRY, 1998, 9 (21) :3741-3744
[27]  
Lucet D, 1998, ANGEW CHEM INT EDIT, V37, P2581, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2580::AID-ANIE2580>3.0.CO
[28]  
2-L
[29]  
MAKKOV AV, 2001, TETRAHEDRON LETT, V42, P509
[30]   Design and synthesis of novel tridentate and tetradentate chiral ligands [J].
Neuville, L ;
Chastanet, J ;
Zhu, JP .
TETRAHEDRON LETTERS, 1999, 40 (39) :7087-7090