(η6-Arene)RuII/Chiral SN Ligand: A Novel Bifunctional Catalyst System for Asymmetric Transfer Hydrogenation of Aromatic Ketones

被引:27
作者
Ito, Masato [1 ]
Shibata, Yuji [1 ]
Watanabe, Akira [1 ]
Ikariya, Takao [1 ]
机构
[1] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan
关键词
RuCl2(eta(6)-arene)](2); protic aminothiol ligand; asymmetric transfer hydrogenation; aromatic ketone; bifunctionality; CP-ASTERISK-RU(PN) COMPLEXES; MOLECULAR CATALYSTS; FORMIC-ACID; ALCOHOLS; RUTHENIUM; SULFIDES; BEARING; FUNCTIONALITIES; RACEMIZATION;
D O I
10.1055/s-0029-1217349
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A binary catalyst system of [RuCl2(eta(6)-arene)](2) and a erotic aminothiol (SN) ligand has been found to promote hydrogen transfer between alcohols and carbonyl compounds. The chiral catalyst system with the pipecolinol-derived chiral SN ligand displays excellent stereoselectivity in the asymmetric transfer hydrogenation of aromatic ketones using HCO2H-Et3N. Novel unsymmetrical bis(thiolate)-bridged binuclear complex, which is relevant to the generation of catalytically active species, has been synthesized and structurally characterized.
引用
收藏
页码:1621 / 1626
页数:6
相关论文
共 35 条
[1]   2-azanorbornyl alcohols: Very efficient ligands for ruthenium-catalyzed asymmetric transfer hydrogenation of aromatic ketones [J].
Alonso, DA ;
Nordin, SJM ;
Roth, P ;
Tarnai, T ;
Andersson, PG ;
Thommen, M ;
Pittelkow, U .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3116-3122
[2]   HIGHLY FLUXIONAL ARENE CYCLOOCTATETRAENE COMPLEXES OF ZEROVALENT IRON, RUTHENIUM, AND OSMIUM - SINGLE-CRYSTAL X-RAY STUDY OF (CYCLOOCTATETRAENE)(HEXAMETHYLBEZENE)RUTHENIUM(0), RU(ETA-6-HMB)(1-4-ETA-COT) [J].
BENNETT, MA ;
MATHESON, TW ;
ROBERTSON, GB ;
SMITH, AK ;
TUCKER, PA .
INORGANIC CHEMISTRY, 1980, 19 (04) :1014-1021
[3]   (ETA-6-HEXAMETHYLBENZENE)RUTHENIUM COMPLEXES [J].
BENNETT, MA ;
HUANG, TN ;
MATHESON, TW ;
SMITH, AK .
INORGANIC SYNTHESES, 1982, 21 :74-78
[4]  
BRUK YA, 1970, J GEN CHEM USSR, V40, P2300
[5]   [(ETA(6)-C(6)H(3)ME(3))RU(D-PEN)](2)CL-2-CENTER-DOT-4H(2)O [J].
CAPPER, G ;
DAVIES, DL ;
FAWCETT, J ;
RUSSELL, DR .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1995, 51 :578-580
[6]  
Carroll F.I., 1963, J. Org. Chem, V28, P1236, DOI DOI 10.1021/JO01040A017
[7]   HOMODIMERIC AND HETERODIMERIC BIS(AMINO THIOL) OXOMETAL COMPLEXES WITH RHENIUM(V) AND TECHNETIUM(V) - CONTROL OF HETERODIMERIC COMPLEX-FORMATION AND AN APPROACH TO METAL-COMPLEXES THAT MIMIC STEROID-HORMONES [J].
CHI, DY ;
ONEIL, JP ;
ANDERSON, CJ ;
WELCH, MJ ;
KATZENELLENBOGEN, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (07) :928-937
[8]   Efficient ruthenium-catalyzed racemization of secondary alcohols: application to dynamic kinetic resolution [J].
Dijksman, A ;
Elzinga, JM ;
Li, YX ;
Arends, IWCE ;
Sheldon, RA .
TETRAHEDRON-ASYMMETRY, 2002, 13 (08) :879-884
[9]   ASYMMETRISCHE KATALYSE DER INTRAMOLEKULAREN CANNIZZARO-REAKTION [J].
FRANZEN, V .
CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (09) :2036-2039
[10]   Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture [J].
Fujii, A ;
Hashiguchi, S ;
Uematsu, N ;
Ikariya, T ;
Noyori, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2521-2522