Highly enantioselective Henry reaction catalyzed by chiral tridentate heteroorganic ligands

被引:33
|
作者
Rachwalski, Michal [1 ,2 ]
Lesniak, Stanislaw [1 ]
Sznajder, Ewelina [1 ]
Kielbasinski, Piotr [2 ]
机构
[1] Univ Lodz, Dept Organ & Appl Chem, PL-90136 Lodz, Poland
[2] Polish Acad Sci, Ctr Mol & Macromol Studies, Dept Heteroorgan Chem, PL-90363 Lodz, Poland
关键词
NITROALDOL REACTION; COMPLEXES;
D O I
10.1016/j.tetasy.2009.06.015
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
New tridentate enantiomerically pure heteroatom catalysts, containing hydroxyl, sulfinyl and amino groups, proved to be highly efficient in the enantioselective nitroaldol (Henry) reaction to give the desired adducts in very high yields (Lip to 90%) and with ees up to 98%. The influence of the stereogenic centres located on the sulfinyl sulfur atom and in the amine moiety is also discussed. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1547 / 1549
页数:3
相关论文
共 50 条
  • [41] Highly Enantioselective Hydrogenation of α-Arylmethylene Cycloalkanones Catalyzed by Iridium Complexes of Chiral Spiro Aminophosphine Ligands
    Xie, Jian-Bo
    Xie, Jian-Hua
    Liu, Xiao-Yan
    Kong, Wei-Ling
    Li, Shen
    Zhou, Qi-Lin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (13) : 4538 - +
  • [42] Synthesis of Chiral Tetrahydroisoquinoline and C2-Symmetric Bistetrahydroisoquinoline Ligands and Their Application in the Enantioselective Henry Reaction
    Duc Thinh Khong
    Judeh, Zaher M. A.
    [J]. SYNTHESIS-STUTTGART, 2016, 48 (14): : 2271 - 2279
  • [43] Enantioselective Henry Reaction Catalyzed by "Ship in a Bottle" Complexes
    Bania, Kusum K.
    Karunakar, Galla V.
    Goutham, Kommuru
    Deka, Ramesh C.
    [J]. INORGANIC CHEMISTRY, 2013, 52 (14) : 8017 - 8029
  • [44] Enantioselective Henry Reaction Catalyzed by CuII Salt and Bipiperidine
    Noole, Artur
    Lippur, Kristin
    Metsala, Andrus
    Lopp, Margus
    Kanger, Tonis
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (04): : 1313 - 1316
  • [45] Synthesis of novel chiral tridentate aminophenol ligands for enantioselective addition of diethylzinc to aldehydes
    Yang, Xiao-Feng
    Hirose, Takuji
    Zhang, Guang-You
    [J]. TETRAHEDRON-ASYMMETRY, 2008, 19 (14) : 1670 - 1675
  • [46] Chiral tridentate C-2 diphosphine ligands for enantioselective catalysis.
    Sablong, R
    Newton, C
    Dierkes, P
    Osborn, JA
    [J]. TETRAHEDRON LETTERS, 1996, 37 (28) : 4933 - 4936
  • [47] Chiral bifunctional ferrocenylphosphine catalyzed highly enantioselective [3+2] cycloaddition reaction
    Hu, Haiwen
    Yu, Shuxian
    Zhu, Linglong
    Zhou, Lingxiu
    Zhong, Weihui
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (02) : 752 - 760
  • [48] Highly enantioselective Diels-Alder reaction catalyzed by chiral phosphate magnesium complex
    Li, Guilong
    Liang, Tao
    Antilla, Jon C.
    Wojtas, Lukasz
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [49] Chiral Tridentate Ligands in Transition Metal-Catalyzed Asymmetric Hydrogenation
    Wang, Heng
    Wen, Jialin
    Zhang, Xumu
    [J]. CHEMICAL REVIEWS, 2021, 121 (13) : 7530 - 7567
  • [50] Synthesis of chiral tridentate ligands for titanium and tantalum catalyzed asymmetric hydroamination
    Johnson, Adam
    Mitchell, Benjamin
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255