Synthesis and characterization of a Zn(II) complex of a pyrazole-based ligand bearing a chiral L-alaninemethylester

被引:42
作者
Roh, SG
Park, YC
Park, DK
Kim, TJ
Jeong, JH [1 ]
机构
[1] Kyungpook Natl Univ, Dept Chem, Taegu 702701, South Korea
[2] Kyungpook Natl Univ, Dept Ind Chem, Taegu 702701, South Korea
基金
新加坡国家研究基金会;
关键词
crystal structures; zinc complexes; chiral N-substituted pyrazole;
D O I
10.1016/S0277-5387(01)00788-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Reaction of ZnCl2 with a new ligand N,N-bis(3,5-dimethylpyrazolylmethyl)-L-alaninemethylester (bdmpame) in methanol gives [ZnCl2(bdmpame)]. The structure of [ZnCl2(bdmpame)]. CH2Cl2 has been resolved by X-ray crystallographic analysis. The Zn atom has a distorted tetrahedral geometry involving a nitrogen atom from each pyrazole in bdmpame and two chloro ligands with bond lengths in the range 2.037(4)-2.237(2) Angstrom. The nitrogen atom of the L-alaninemethylester group in the compound was not coordinated to the metal center, giving an eight-membered ring in which the nitrogen atoms of each pyrazole in bdmpame are coordinated to the metal center. The results of the catalytic enantioselective reduction of acetophenone promoted by ligand/Zn(OTf)(2) = 1:1 mole ratio in the presence of catecholborane for 48 h at 0 degreesC gives (S)-(-)-1-phenylethanol in 21% ee with 68% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1961 / 1965
页数:5
相关论文
共 47 条
[1]   A MONONUCLEAR ZINC HYDROXIDE COMPLEX STABILIZED BY A HIGHLY SUBSTITUTED TRIS(PYRAZOLY)HYDROBORATO LIGAND - ANALOGIES WITH THE ENZYME CARBONIC-ANHYDRASE [J].
ALSFASSER, R ;
TROFIMENKO, S ;
LOONEY, A ;
PARKIN, G ;
VAHRENKAMP, H .
INORGANIC CHEMISTRY, 1991, 30 (21) :4098-4100
[2]  
[Anonymous], 1986, ZINC ENZYMES
[3]   Zinc triflate-bis-oxazoline complexes as chiral catalysts:: enantioselective reduction of α-alkoxy-ketones with catecholborane [J].
Bandini, M ;
Cozzi, PG ;
de Angelis, M ;
Umani-Ronchi, A .
TETRAHEDRON LETTERS, 2000, 41 (10) :1601-1605
[4]   POTENTIAL METAL-BINDING DOMAINS IN NUCLEIC-ACID BINDING-PROTEINS [J].
BERG, JM .
SCIENCE, 1986, 232 (4749) :485-487
[5]   STRUCTURE OF 1-PERCENT COPPER(II)-DOPED DICHLOROBIS(1,2-DIMETHYLIMIDAZOLE)ZINC(II) [J].
BHARADWAJ, PK ;
SCHUGAR, HJ ;
POTENZA, JA .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 :754-757
[6]   Zinc(II) and copper(II) complexes of pentacoordinating (N4S) ligands with flexible pyrazolyl arms: Syntheses, structure, and redox and spectroscopic properties [J].
Bhattacharyya, S ;
Kumar, SB ;
Dutta, SK ;
Tiekink, ERT ;
Chaudhury, M .
INORGANIC CHEMISTRY, 1996, 35 (07) :1967-1973
[7]   O-2(-) SCAVENGER PROPERTIES OF COPPER(II) COMPLEXES WITH DIAMINO-DIAMIDE-TYPE LIGANDS [J].
BONOMO, RP ;
CONTE, E ;
MARCHELLI, R ;
SANTORO, AM ;
TABBI, G .
JOURNAL OF INORGANIC BIOCHEMISTRY, 1994, 53 (02) :127-138
[8]   COORDINATION-COMPOUNDS OF A PENTADENTATE PYRAZOLE DERIVATIVE OF DIAMINOPROPANE - CRYSTAL-STRUCTURE OF AQUA(N,N,N'-TRIS((3,5-DIMETHYLPYRAZOL-1-YL)METHYL)-1,3-DIAMINOPROPANE)COBALT(II) DIPERCHLORATE HYDRATE, [CO(AP3D)(H2O)](CLO4)2.H2O [J].
BOUWMAN, E ;
DRIESSEN, WL ;
REEDIJK, J .
INORGANIC CHEMISTRY, 1985, 24 (26) :4730-4733
[9]   BIS(PYRAZOL-1-YL)PROPANE AS A BULKY LIGAND - X-RAY CRYSTAL-STRUCTURE DETERMINATION OF ITS ADDUCT WITH ZINC(II) CHLORIDE [J].
BOVIO, B ;
CINGOLANI, A ;
BONATI, F .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1992, 610 (04) :151-156
[10]   Zinc thiolate complexes with chelating nitrogen ligands [J].
Burth, R ;
Vahrenkamp, H .
INORGANICA CHIMICA ACTA, 1998, 282 (02) :193-199