Copper-catalyzed enantioselective conjugate addition of triethylaluminum to 2-cyclopentenone

被引：28
|
作者：
Su, LM [1 ]
Li, XS [1 ]
Chan, WL [1 ]
Jia, X [1 ]
Chan, ASC [1 ]
机构：
[1] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 13期
关键词：
D O I：
10.1016/S0957-4166(03)00349-5
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Bidentate phosphites were prepared starting from BINOL, H-8-BINOL or 3,3', 5,5'-tetra-tert-butyl-2,2'-biphenol. Utilization of these ligands in the copper-catalyzed enantioselective conjugate addition of triethylaluminum to 2-cyclopentenone afforded 3-ethylcyclopentanone in up to 94.0% ee. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1865 / 1869
页数：5
相关论文
共 50 条
  • [41] Copper-catalyzed enantioselective intramolecular conjugate addition/trapping reactions: Synthesis of cyclic compounds with multichiral centers
    Li, Kangying
    Alexakis, Alexandre
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (13) : 3765 - 3771
  • [42] Enantioselective synthesis of propargylamines by copper-catalyzed addition of alkynes to enamines
    Koradin, C
    Polborn, K
    Knochel, P
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (14) : 2535 - +
  • [43] Rhodium and copper-catalyzed asymmetric conjugate addition of alkenyl nucleophiles
    Mueller, Daniel
    Alexakis, Alexandre
    CHEMICAL COMMUNICATIONS, 2012, 48 (99) : 12037 - 12049
  • [44] TRANSMETALATION REACTIONS OF ALKYLZIRCONOCENES - COPPER-CATALYZED CONJUGATE ADDITION TO ENONES
    WIPF, P
    SMITROVICH, JH
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23): : 6494 - 6496
  • [45] TRANSMETALATION REACTIONS OF ALKENYLALANES - COPPER-CATALYZED CONJUGATE ADDITION TO ENONES
    WIPF, P
    SMITROVICH, JH
    MOON, CW
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (11): : 3178 - 3186
  • [46] Copper-Catalyzed Asymmetric Conjugate Addition with Chiral SimplePhos Ligands
    Palais, Laetitia
    Alexakis, Alexandre
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (40) : 10473 - 10485
  • [47] Aromatic Heterocycles as Activating Groups for Asymmetric Conjugate Addition Reactions. Enantioselective Copper-Catalyzed Reduction of 2-Alkenylheteroarenes
    Rupnicki, Leszek
    Saxena, Aakarsh
    Lam, Hon Wai
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (30) : 10386 - +
  • [48] Enantioselective Copper-Catalyzed Conjugate Addition of Dimethylzinc to 5-(1-Arylalkylidene) Meldrum's Acids
    Wilsily, Ashraf
    Lou, Tiantong
    Fillion, Eric
    SYNTHESIS-STUTTGART, 2009, (12): : 2066 - 2072
  • [49] Photoinduced Enantioselective Triplet Radical Reaction on Metal: Copper-Catalyzed Conjugate Addition of Acylsilanes to α,β-Unsaturated Ketones and Aldehydes
    Masuda, Yusuke
    Ueda, Yusuke
    Sueki, Aiko
    Shimosato, Junpei
    Nishimura, Kousei
    Gao, Min
    Hasegawa, Jun-ya
    Sawamura, Masaya
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (65)
  • [50] Highly enantioselective copper-catalyzed 1,4-conjugate addition of diethylzinc to cyclic enones and α,β-unsaturated lactones
    Liang, L
    Yan, M
    Li, YM
    Chan, ASC
    TETRAHEDRON-ASYMMETRY, 2004, 15 (16) : 2575 - 2578
12345