New C2-symmetric bis(sulfonamide)-cyclohexane-1,2-diamine-RhCp* complex and its application in the asymmetric transfer hydrogenation (ATH) of ketones in water

被引：41

作者：

Cortez, Norma A.

Rodriguez-Apodaca, Ramon

Aguirre, Gerardo

Parra-Hake, Miguel

Cole, Thomas

Somanathan, Ratnasamy

机构：

[1] Inst Tecnol Tijuana, Ctr Grad & Invest, Tijuana 22500, Mexico

[2] San Diego State Univ, Dept Chem, San Diego, CA 92182 USA

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 48期

关键词：

bis(sulfonamide) ligands; RhCp* complex; asymmetric transfer hydrogenation; ketones;

D O I：

10.1016/j.tetlet.2006.09.141

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C-2-symmetric bis(sulfonamide) ligands derived from trans-(1R,2R)-cyclohexane-1,2-diamine were synthesized and complexed with [Cp*RhCl2](2) in situ and used in the ATH of aromatic ketones with aqueous sodium formate as the hydrogen source. The chiral secondary alcohols were obtained with 90-99% enantioselectivity and in 50-100% yield. Reductions in water were faster than those in isopropanol/KOH. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：8515 / 8518

页数：4

共 54 条

[1] Chiral ferrocenyl diphosphines for asymmetric transfer hydrogenation of acetophenone
Cabou, J
Brocard, J
Pélinski, L
[J]. TETRAHEDRON LETTERS, 2005, 46 (07) : 1185 - 1188
[2] Synthesis of substituted mandelic acid derivatives via enantioselective hydrogenation:: Homogeneous versus heterogeneous catalysis
Cederbaum, F
Lamberth, C
Malan, C
Naud, F
Spindler, F
Studer, M
Blaser, HU
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (07) : 842 - 848
[3] Dendritic catalysts for asymmetric transfer hydrogenation
Chen, YC
Wu, TF
Deng, JG
Liu, H
Jiang, YZ
Choib, MCK
Chan, ASC
[J]. CHEMICAL COMMUNICATIONS, 2001, (16) : 1488 - 1489
[4] Tethered Ru(II) catalysts for asymmetric transfer hydrogenation of ketones
Cheung, FK
Hayes, AM
Hannedouche, J
Yim, ASY
Wills, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) : 3188 - 3197
[5] Collins A.N., 1992, CHIRALITY IND COMMER
[6] Transfer hydrogenation reduction of acetophenone catalyzed by Ru(II) and Rh(I) complexes with ligands derived from (1R,2R)-cyclohexane-1,2-diamine
Cortez, NA
Flores-López, CZ
Rodríguez-Apodaca, R
Flores-López, LZ
Parra-Hake, M
Somanathan, R
[J]. ARKIVOC, 2005, : 162 - 171
[7] Ruthenium(II)-assisted asymmetric hydrogen transfer reduction of acetophenone using chiral tridentate phosphorus-containing ligands derived from (1R, 2R)-1,2-diaminocyclohexane
Flores-López, CZ
Flores-López, LZ
Aguirre, G
Hellberg, LH
Parra-Hake, M
Somanathan, R
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 215 (1-2) : 73 - 79
[8] Preparation of new, optically active 1,2-ferrocenyldiamine ligands and their application to ruthenium-catalyzed asymmetric transfer hydrogenation of ketones
Fukuzawa, S
Suzuki, T
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (04) : 1012 - 1016
[9] Asymmetric transfer hydrogenation: chiral ligands and applications
Gladiali, S
Alberico, E
[J]. CHEMICAL SOCIETY REVIEWS, 2006, 35 (03) : 226 - 236
[10] A modular design of ruthenium catalysts with diamine and BINOL-derived phosphinite ligands that are enantiomerically-matched for the effective asymmetric transfer hydrogenation of simple ketones
Guo, RW
Elpelt, C
Chen, XH
Song, DT
Morris, RH
[J]. CHEMICAL COMMUNICATIONS, 2005, (24) : 3050 - 3052

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