Stereoselective hydrogenation of methyl acetoacetate over structurally different chiral ruthenium complexes

被引：12
作者：
Floris, Tomas [2 ]
Kluson, Petr [1 ]
Slater, Morwenna [3 ]
机构：
[1] Acad Sci Czech Republ, Inst Chem Proc Fundamentals, CR-16502 Prague, Czech Republic
[2] Fac Chem Technol, Inst Chem Technol ICT Prague, Prague 16628, Czech Republic
[3] Bangor Univ, Sch Chem, N Wales LL57 2UW, Gwynedd, Wales
来源：
REACTION KINETICS MECHANISMS AND CATALYSIS | 2011年 / 102卷 / 01期
关键词：
Ru-BINAP complex; Enantioselectivity; Optical yield; Stereoselective hydrogenation; ASYMMETRIC HYDROGENATION; ENANTIOSELECTIVE HYDROGENATION; CARBOXYLIC-ACIDS; BINAP; STEREOCHEMISTRY; PHOSPHINE; ALCOHOLS; CATALYST; KETONES;
D O I：
10.1007/s11144-010-0256-1
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：
Structurally different chiral ruthenium complexes were used in the asymmetric hydrogenation of methyl acetoacetate to methyl (R)-3-hydroxybutanoate. The naphthalene and dioxazole biphosphine structure variations revealed a strong effect on the reaction rate and the parameter of enantioselectivity. The highest optical yields were achieved with catalysts bearing two metal centers and comprising the quaternary ammonium ionic character.
引用
收藏
页码：67 / 74
页数：8
相关论文
共 24 条
[1]   Catalytic cycle for the asymmetric hydrogenation of prochiral ketones to chiral alcohols:: Direct hydride and proton transfer from chiral catalysts trans-Ru(H)2(diphosphine)(diamine) to ketones and direct addition of dihydrogen to the resulting hydridoamido complexes [J].
Abdur-Rashid, K ;
Faatz, M ;
Lough, AJ ;
Morris, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) :7473-7474
[2]   Asymmetric Hydrogenation of Bicyclic Ketones Catalyzed by BINAP/IPHAN-Ru(II) Complex [J].
Arai, Noriyoshi ;
Akashi, Masaya ;
Sugizaki, Satoshi ;
Ooka, Hirohito ;
Inoue, Tsutomu ;
Ohkuma, Takeshi .
ORGANIC LETTERS, 2010, 12 (15) :3380-3383
[3]   Notes on acetal formation in stereoselective hydrogenation of methyl-3-oxobutyrate on Ru-BINAP chiral complex [J].
Bartek, L ;
Drobek, M ;
Kuzma, M ;
Kluson, P ;
Cerveny, L .
CATALYSIS COMMUNICATIONS, 2005, 6 (01) :61-65
[4]   SYNTHESIS AND CATALYTIC PROPERTIES OF RHODIUM-(+)DIOP COMPLEXES [J].
CHAUVIN, Y ;
COMMEREUC, D ;
STERN, R .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 146 (03) :311-318
[5]   Enantioselective hydrogenation with racemic and enantiopure binap in the presence of a chiral ionic liquid [J].
Chen, Dianjun ;
Schmitkamp, Mike ;
Francio, Giancarlo ;
Klankermayer, Juergen ;
Leitner, Walter .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (38) :7339-7341
[6]   mer-[RuCl3(P-P)H2O] (P-P=dppb or diop) as a starting material for the synthesis of binuclear complexes.: Crystallographic structures of [(dppb)ClRu-μ(Cl)3-RuCl(dppb)] and [(η6-C6H6)Ru-μ(Cl)3-RuCl(dppb)].: Imine hydrogenation using mono- and binuclear ruthenium complexes [J].
de Araujo, MP ;
Valle, EMA ;
Ellena, J ;
Castellano, EE ;
dos Santos, EN ;
Batista, AA .
POLYHEDRON, 2004, 23 (18) :3163-3172
[7]   A highly effective water-soluble polymer-supported catalyst for the two-phase asymmetric hydrogenation: preparation and use of a PEG-bound BINAP ligand [J].
Fan, QH ;
Deng, GJ ;
Chen, XM ;
Xie, WC ;
Jiang, DZ ;
Liu, DS ;
Chan, ASC .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2000, 159 (01) :37-43
[8]   Notes on the Asymmetric Hydrogenation of Methyl Acetoacetate in Neoteric Solvents [J].
Floris, Tomas ;
Kluson, Petr ;
Muldoon, Mark J. ;
Pelantova, Helena .
CATALYSIS LETTERS, 2010, 134 (3-4) :279-287
[9]   Quaternary ammonium salts ionic liquids for immobilization of chiral Ru-BINAP complexes in asymmetric hydrogenation of β-ketoesters [J].
Floris, Tomas ;
Kluson, Petr ;
Bartek, Lukas ;
Pelantova, Helena .
APPLIED CATALYSIS A-GENERAL, 2009, 366 (01) :160-165
[10]   Continuous Enantioselective Hydrogenation with a Molecular Catalyst in Supported Ionic Liquid Phase under Supercritical CO2 Flow [J].
Hintermair, Ulrich ;
Hoefener, Tobias ;
Pullmann, Thomas ;
Francio, Giancarlo ;
Leitner, Walter .
CHEMCATCHEM, 2010, 2 (02) :150-154
123