Synthesis, characterization and application of Ru(BINAP)(Acac)(MNAA)(MeOH), a highly effective catalyst for the asymmetric hydrogenation of 2-(6′-methoxynaphth-2′-yl)acrylic acid

被引:16
作者
Chen, CC
Huang, TT
Lin, CW
Cao, R
Chan, ASC [1 ]
Wong, WT
机构
[1] Hong Kong Polytech Univ, Union Lab Asymmetr Synth, Hong Kong, Peoples R China
[2] Univ Hong Kong, Dept Chem, Hong Kong, Peoples R China
[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Peoples R China
关键词
asymmetric hydrogenation; ruthenium complexes; BINAP complexes; acetylacetonate complexes; acrylate anion complexes;
D O I
10.1016/S0020-1693(97)05850-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Ru(S-BINAP) (Acac) (MNAA) (MeOH) (1) (where MNAA (2) = 2-(6'-methoxynaphth-2'-yl) acrylate anion), a highly effective catalyst for the asymmetric hydrogenation of 2-(6'-methoxynaphth-2'-yl) acrylic acid (3)!, was isolated from a dichloromethane/methanol (vol./vol. = 1/4) solution of Ru(S-BINAP) (Acac), and excess of 2-(6'-methoxynaphth-2'-yl)acrylic acid after the solution was exposed to visible light for 2 weeks. On side by side comparison studies, the rate of the hydrogenation of 3 catalyzed by 1 was found to be substantially faster than the same reaction catalyzed by Ru(S-BINAP) (OAc)(2). The molecular structure of 1 was unambiguously characterized by single crystal X-ray diffraction. (C) 1998 Elsevier Science S.A.
引用
收藏
页码:247 / 251
页数:5
相关论文
共 20 条
[1]  
[Anonymous], 1992, TEXSAN CRYST STRUCT
[2]  
[Anonymous], ASYMMETRIC SYNTHESIS
[3]  
[Anonymous], 1985, TEXSAN CRYST STRUCT
[4]   CRYSTAL AND MOLECULAR-STRUCTURE OF AN ASYMMETRIC HYDROGENATION CATALYST SUBSTRATE ADDUCT, DELTA-BIS(TIGLATO)((R)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL)-RUTHENIUM(II), [RUII(BINAP)(O2CCME=CHME)2] [J].
ASHBY, MT ;
KHAN, MA ;
HALPERN, J .
ORGANOMETALLICS, 1991, 10 (06) :2011-2015
[5]  
BOSNICH B, 1986, ASYMMETRIC CATALYSIS, P19
[6]  
BRUNNER H, 1988, SYNTHESIS-STUTTGART, P645
[7]   SIR88 - A DIRECT-METHODS PROGRAM FOR THE AUTOMATIC SOLUTION OF CRYSTAL-STRUCTURES [J].
BURLA, MC ;
CAMALLI, M ;
CASCARANO, G ;
GIACOVAZZO, C ;
POLIDORI, G ;
SPAGNA, R ;
VITERBO, D .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1989, 22 :389-393
[8]  
Chan A., 1991, U.S. Patent, Patent No. 4994607
[9]   PREPARATION AND STRUCTURAL CHARACTERIZATION OF BIS(ACETYLACETONATO)RUTHENIUM(II)-BINAP - AN EFFICIENT ROUTE TO AN EFFECTIVE ASYMMETRIC HYDROGENATION CATALYST PRECURSOR [J].
CHAN, AS ;
LANEMAN, SA ;
DAY, CX .
INORGANICA CHIMICA ACTA, 1995, 228 (02) :159-163
[10]  
CHAN ASC, 1992, Patent No. 5144050