New, chiral phase transfer catalysts for effecting asymmetric conjugate additions of α-alkyl-α-cyanoacetates to acetylenic esters

被引:99
|
作者
Wang, Xisheng [1 ]
Kitamura, Masanori [1 ]
Maruoka, Keiji [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
关键词
D O I
10.1021/ja068119g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new, chiral phase transfer catalyst has been designed for the development of a general and useful procedure on the hitherto unknown, asymmetric conjugate additions of alpha-substituted-alpha-cyanoacetates to acetylenic esters with high enantioselectivity and moderate E/Z selectivity.
引用
收藏
页码:1038 / 1039
页数:2
相关论文
共 50 条
  • [1] Asymmetric conjugate additions of α-substituted-α-cyanoacetates to acetylenic ketones by chiral phase transfer catalysis
    Lan, Quan
    Wang, Xisheng
    Maruoka, Keiji
    TETRAHEDRON LETTERS, 2007, 48 (27) : 4675 - 4678
  • [2] Phase-Transfer Catalyzed Asymmetric Conjugate Additions of β-Ketoesters to Acetylenic Ketones
    Lan, Quan
    Wang, Xisheng
    Shirakawa, Seiji
    Maruoka, Keiji
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (03) : 684 - 686
  • [3] Powerful chiral phase-transfer catalysts for the asymmetric synthesis of α-alkyl- and α,α,-dialkyl-α-amino acids
    Kitamra, M
    Shirakawa, S
    Maruoka, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (10) : 1549 - 1551
  • [4] Chiral bifunctional phase transfer catalysts for asymmetric fluorination of β-keto esters
    Wang, Xisheng
    Lan, Quan
    Shirakawa, Seiji
    Maruoka, Keiji
    CHEMICAL COMMUNICATIONS, 2010, 46 (02) : 321 - 323
  • [5] Combinatorial approach for the design of new, simplified chiral phase-transfer catalysts with high catalytic performance for practical asymmetric synthesis of α-alkyl-α-amino acids
    Kitamura, Masanori
    Arimura, Yuichiro
    Shirakawa, Seiji
    Maruoka, Keiji
    TETRAHEDRON LETTERS, 2008, 49 (12) : 2026 - 2030
  • [6] Asymmetric conjugate reduction of α,β-unsaturated esters with chiral rhodium(bisoxazolinylphenyl) catalysts
    Tsuchiya, Y
    Kanazawa, Y
    Shiomi, T
    Kobayashi, K
    Nishiyama, H
    SYNLETT, 2004, (14) : 2493 - 2496
  • [7] SYNTHESIS OF NEW CHIRAL PHASE-TRANSFER CATALYSTS AND THEIR APPLICATION TO MICHAEL ADDITIONS
    BANFI, S
    CINQUINI, M
    COLONNA, S
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (06) : 1841 - 1843
  • [8] Octahedral Chiral-at-Metal Iridium Catalysts: Versatile Chiral Lewis Acids for Asymmetric Conjugate Additions
    Shen, Xiaodong
    Huo, Haohua
    Wang, Chuanyong
    Zhang, Bo
    Harms, Klaus
    Meggers, Eric
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (27) : 9720 - 9726
  • [9] Chiral camphor derivatives as new catalysts for asymmetric phase-transfer alkylation
    Zhang, J
    Wu, XY
    Zhou, QL
    Sun, J
    CHINESE JOURNAL OF CHEMISTRY, 2001, 19 (06) : 630 - 633
  • [10] Asymmetric Michael reaction promoted by new chiral phase-transfer catalysts
    Arai, S
    Tokumaru, K
    Aoyama, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2004, 52 (05) : 646 - 648