A highly efficient asymmetric Michael addition of anthrone to nitroalkenes with cinchona organocatalysts

被引:61
|
作者
Shi, Min
Lei, Zhi-Yu
Zhao, Mei-Xin
Shi, Jing-Wen
机构
[1] E China Univ Chem Technol, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
Michael addition; nitroalkenes; anthrone; cinchona; alkaloids;
D O I
10.1016/j.tetlet.2007.06.107
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient asymmetric Michael addition of anthrone to nitroalkenes catalyzed by cinchona alkaloids was described. Up to 99% ee of the corresponding adduct was obtained. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5743 / 5746
页数:4
相关论文
共 50 条
  • [1] Application of L-prolinamides as highly efficient organocatalysts for the asymmetric Michael addition of unmodified aldehydes to nitroalkenes
    Naziroglu, Hayriye Nevin
    Durmaz, Mustafa
    Bozkurt, Selahattin
    Demir, Ayhan Sitki
    Sirit, Abdulkadir
    TETRAHEDRON-ASYMMETRY, 2012, 23 (02) : 164 - 169
  • [2] Chiral Polyureas Derived Cinchona Alkaloids: Highly Efficient Bifunctional Organocatalysts for the Asymmetric Michael Addition Reaction
    Abdelkawy, Mahmoud A.
    Davin, Christopher
    Aly, El-Saied A.
    El-Badawi, Mahmoud A.
    Itsuno, Shinichi
    CHEMISTRYSELECT, 2021, 6 (43): : 11971 - 11979
  • [3] Effective asymmetric Michael addition of anthrone to nitroalkenes using chiral tetraoxacalix[2]arene[2]triazines as organocatalysts
    Genc, Hayriye Nevin
    CHIRALITY, 2019, 31 (09) : 711 - 718
  • [4] Highly efficient asymmetric Michael addition of aldehydes to nitroalkenes with 4,5-methano-L-proline as organocatalysts
    Yu, Han
    Liu, Mouming
    Han, Sheng
    TETRAHEDRON, 2014, 70 (44) : 8380 - 8384
  • [5] Synthesis of chiral polyesters of cinchona alkaloid catalysts for enantioselective Michael addition of anthrone to nitroalkenes
    Kumpuga, Bahati Thom
    Itsuno, Shinichi
    JOURNAL OF CATALYSIS, 2018, 361 : 398 - 406
  • [6] Highly Efficient Asymmetric Michael Reaction of Aldehydes to Nitroalkenes with Diphenylperhydroindolinol Silyl Ethers as Organocatalysts
    Luo, Ren-Shi
    Weng, Jiang
    Ai, Hui-Bing
    Lu, Gui
    Chan, Albert S. C.
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (14-15) : 2449 - 2459
  • [7] Highly efficient bifunctional organocatalysts for the asymmetric Michael addition of ketones to nitroolefins
    Yu, Chuanming
    Qiu, Jun
    Zheng, Fei
    Zhong, Weihui
    TETRAHEDRON LETTERS, 2011, 52 (26) : 3298 - 3302
  • [8] Enantioselective Organocatalytic Michael Addition of Anthrone to Nitroalkenes
    He, Tianxiong
    Wu, Xinyan
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2010, 30 (09) : 1400 - 1404
  • [9] Homodiphenylprolinol Methyl Ether as a Highly Efficient Catalyst for Asymmetric Michael Addition of Ketones to Nitroalkenes
    Wang, Shi-Wen
    Chen, Jun
    Chen, Gui-Hua
    Peng, Yun-Gui
    SYNLETT, 2009, (09) : 1457 - 1462
  • [10] Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes
    Hayashi, Y
    Gotoh, H
    Hayashi, T
    Shoji, M
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (27) : 4212 - 4215