Novel chiral thioureas for highly enantioselective Michael reactions of malonates to nitroalkenes

被引:5
|
作者
Yan, Li Jun [1 ]
Liu, Quan Zhong [1 ]
Wang, Xue Lian [1 ]
机构
[1] China W Normal Univ, Coll Chem & Chem Engn, Lab Appl Chem & Pollut Control Technol, Nanchang 637002, Peoples R China
关键词
Michael addition; Thiourea; Enantioselectivities; Nitroalkene and malonate; ASYMMETRIC CATALYSIS; CONJUGATE ADDITION; ORGANOCATALYSIS; NITROOLEFINS; KETONES; DONORS;
D O I
10.1016/j.cclet.2008.11.021
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Highly efficient Michael addition reactions of malonates to nitroalkenes catalyzed by novel chiral thioureas derived from optically pure BINOL and amino acids are reported. Various trans-nitroalkenes reacted with malonates affording the desired products in up to 95% yield with excellent enantioselectivities (up to 97% ee). (C) 2008 Quan Zhong Liu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
引用
收藏
页码:310 / 313
页数:4
相关论文
共 50 条
  • [2] Highly Enantioselective Michael Addition of Malonates to Nitroolefins Catalyzed by Chiral Bifunctional Tertiary Amine-Thioureas Based on Saccharides
    Li, Xiao-Juan
    Liu, Kun
    Ma, Hai
    Nie, Jing
    Ma, Jun-An
    SYNLETT, 2008, (20) : 3242 - 3246
  • [3] An Efficient Synthesis of Chiral Diamines with Rigid Backbones: Application in Enantioselective Michael Addition of Malonates to Nitroalkenes
    Zhu, Qiming
    Huang, Hanmin
    Shi, Dengjian
    Shen, Zhiqiang
    Xia, Chungu
    ORGANIC LETTERS, 2009, 11 (20) : 4536 - 4539
  • [4] Enantioselective Michael addition of malonates to aromatic nitroalkenes catalyzed by monosaccharide-based chiral crown ethers
    Rapi, Zsolt
    Demuth, Balazs
    Keglevich, Gyoergy
    Grun, Alajos
    Drahos, Laszlo
    Soti, Peter L.
    Bako, Peter
    TETRAHEDRON-ASYMMETRY, 2014, 25 (02) : 141 - 147
  • [5] Highly enantioselective Michael addition of isobutyraldehyde to nitroalkenes
    He, Tianxiong
    Gu, Qing
    Wu, Xin-Yan
    TETRAHEDRON, 2010, 66 (17) : 3195 - 3198
  • [6] High enantioselective Michael addition of malonates to β,γ-unsaturated α-ketoesters catalyzed by bifunctional thioureas
    Konda, Swapna
    Zhao, John C. -G.
    TETRAHEDRON LETTERS, 2014, 55 (37) : 5216 - 5218
  • [7] Highly Enantioselective Michael Addition of Dithiomalonates to Nitroolefins Catalyzed by New Bifunctional Chiral Thioureas
    Yuan, Jia-Ni
    Liu, Hui-Xia
    Tian, Qin-Qin
    Ji, Nan
    Shen, Kuo
    He, Wei
    SYNTHESIS-STUTTGART, 2018, 50 (13): : 2577 - 2586
  • [8] Simple chiral sulfonamide primary amine catalysed highly enantioselective Michael addition of malonates to enones
    Luo, Chunhua
    Jin, Yu
    Du, Da-Ming
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (20) : 4116 - 4123
  • [9] Organocatalytic enantioselective Michael addition of 2,4-pentandione to nitroalkenes promoted by bifunctional thioureas with central and axial chiral elements
    Peng, Fang-Zhi
    Shao, Zhi-Hui
    Fan, Bao-Min
    Song, He
    Li, Gan-Peng
    Zhang, Hong-Bin
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13): : 5202 - 5205
  • [10] Catalytic enantioselective Mukaiyama Michael reactions of alkylidene malonates.
    Rovis, T
    Evans, DA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U211 - U211