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
收藏
页码：8515 / 8518
页数：4
相关论文
共 54 条
[1]   Chiral ferrocenyl diphosphines for asymmetric transfer hydrogenation of acetophenone [J].
Cabou, J ;
Brocard, J ;
Pélinski, L .
TETRAHEDRON LETTERS, 2005, 46 (07) :1185-1188
[2]   Synthesis of substituted mandelic acid derivatives via enantioselective hydrogenation:: Homogeneous versus heterogeneous catalysis [J].
Cederbaum, F ;
Lamberth, C ;
Malan, C ;
Naud, F ;
Spindler, F ;
Studer, M ;
Blaser, HU .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (07) :842-848
[3]   Dendritic catalysts for asymmetric transfer hydrogenation [J].
Chen, YC ;
Wu, TF ;
Deng, JG ;
Liu, H ;
Jiang, YZ ;
Choib, MCK ;
Chan, ASC .
CHEMICAL COMMUNICATIONS, 2001, (16) :1488-1489
[4]   Tethered Ru(II) catalysts for asymmetric transfer hydrogenation of ketones [J].
Cheung, FK ;
Hayes, AM ;
Hannedouche, J ;
Yim, ASY ;
Wills, M .
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 [J].
Cortez, NA ;
Flores-López, CZ ;
Rodríguez-Apodaca, R ;
Flores-López, LZ ;
Parra-Hake, M ;
Somanathan, R .
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 [J].
Flores-López, CZ ;
Flores-López, LZ ;
Aguirre, G ;
Hellberg, LH ;
Parra-Hake, M ;
Somanathan, R .
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 [J].
Fukuzawa, S ;
Suzuki, T .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (04) :1012-1016
[9]   Asymmetric transfer hydrogenation: chiral ligands and applications [J].
Gladiali, S ;
Alberico, E .
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 [J].
Guo, RW ;
Elpelt, C ;
Chen, XH ;
Song, DT ;
Morris, RH .
CHEMICAL COMMUNICATIONS, 2005, (24) :3050-3052
123456