Synthesis and characterization of a chiral Zn(II) complex based on a trans-1,2-diaminocyclohexane derivative and catalytic reduction of acetophenone

被引:43
|
作者
Roh, SG [1 ]
Yoon, JU [1 ]
Jeong, JH [1 ]
机构
[1] Kyungpook Natl Univ, Dept Chem, Taegu 702701, South Korea
关键词
trans-1,2-diaminocyclohexane; crystal structure; zinc complex; catalytic enantioselective reduction;
D O I
10.1016/j.poly.2004.04.033
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Reaction of ZnCl2 with R,R-bmbcd (= N,N'-bis(4-methoxy-benzyl)-cyclohexane-1,2-diamine) I in ethanol yields the chiral [ZnCl2(R,R-bmbcd)] 2, which crystallizes in the monoclinic space group P2(1). The Zn atom has a distorted tetrahedral geometry involving two nitrogen atoms of R, R-bmbcd and two chloro ligands with the range of bond lengths, 2.066(2)-2.2289(9) Angstrom. The result of the catalytic enantioselective reduction of acetophenone promoted by R-1 R-bmbcd:Zn(OTf)(2) = 1:1 mole ratio in the presence of catecholborane for 48 h at 0 degreesC give (S)-(-)-1-phenylethanol in 48% ee with 77% yield. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2063 / 2067
页数:5
相关论文
共 50 条
  • [21] Characteristics of Gelation by Amides Based on trans-1,2-Diaminocyclohexane: The Importance of Different Substituents
    Nakagawa, Haruka
    Fujiki, Mamoru
    Sato, Takaaki
    Suzuki, Masahiro
    Hanabusa, Kenji
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2017, 90 (03) : 312 - 321
  • [22] PREPARATION AND CRYSTAL-STRUCTURE OF BIS(ACETATO)(TRANS-1,2-DIAMINOCYCLOHEXANE)PLATINUM(II)
    ROCHON, FD
    MELANSON, R
    MACQUET, JP
    BELANGERGARIEPY, F
    BEAUCHAMP, AL
    INORGANICA CHIMICA ACTA-BIOINORGANIC CHEMISTRY, 1985, 108 (01): : 17 - 21
  • [23] Novel platinum(II) complexes containing diaminocyclohexane and thiourea derivative ligands: Synthesis and X-ray crystal structure of (trans-1,2-diaminocyclohexane)dithioureaplatinum(II) nitrate monohydrate
    Fang, Jing
    Wei, Xin
    Sapp, John B.
    Deng, Yuanjian
    INORGANICA CHIMICA ACTA, 2014, 411 : 5 - 10
  • [24] New Class of Chiral, Inclusion Forming Crystals with Host Molecules Derived from trans-1,2-Diaminocyclohexane
    Rychlewska, Urszula
    Plutecka, Agnieszka
    ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2006, 62 : S222 - S222
  • [25] Syntheses, crystal structures and solid state thermochromism of copper(II) complexes of trans-1,2-diaminocyclohexane
    Pariya, C.
    Liao, F.-L.
    Wang, S.-L.
    Chung, C.-S.
    Polyhedron, 17 (04):
  • [26] Syntheses, crystal structures and solid state thermochromism of copper(II) complexes of trans-1,2-diaminocyclohexane
    Pariya, C
    Liao, FL
    Wang, SL
    Chung, CS
    POLYHEDRON, 1998, 17 (04) : 547 - 554
  • [27] Lanthanide-Based Complexes Containing a Chiral trans-1,2-Diaminocyclohexane (DACH) Backbone: Spectroscopic Properties and Potential Applications
    Piccinelli, Fabio
    Nardon, Chiara
    Bettinelli, Marco
    Melchior, Andrea
    Tolazzi, Marilena
    Zinna, Francesco
    Di Bari, Lorenzo
    CHEMPHOTOCHEM, 2022, 6 (02):
  • [28] Chiral trans-1,2-diaminocyclohexane derivatives as chiral solvating agents for carboxylic acids (vol 122, pg 561, 2010)
    Periasamy, Mariappan
    Dalai, Manasi
    Padmaja, Meduri
    JOURNAL OF CHEMICAL SCIENCES, 2011, 123 (03) : 365 - 365
  • [29] Equilibrium studies on complex formation reactions of dichlorido[(R,R)-trans-1,2-diaminocyclohexane]platinum(II) complex with ligands of biological significance
    Jelic, Ratomir
    Markovic, Smiljana
    Petrovic, Biljana
    MONATSHEFTE FUR CHEMIE, 2011, 142 (10): : 985 - 992
  • [30] Equilibrium studies on complex formation reactions of dichlorido[(R,R)-trans-1,2-diaminocyclohexane]platinum(II) complex with ligands of biological significance
    Ratomir Jelić
    Smiljana Marković
    Biljana Petrović
    Monatshefte für Chemie - Chemical Monthly, 2011, 142 : 985 - 992