Tandem asymmetric conjugate addition-enolacetates formation of enantiomerically enriched zinc and aluminium enolates

被引:27
|
作者
Vuagnoux-d'Augustin, Magall [1 ]
Alexakis, Alexandre [1 ]
机构
[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland
关键词
D O I
10.1016/j.tetlet.2007.07.220
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The metal enolates, resulting from the copper-catalyzed enantio selective conjugate addition of organometallic reagents (Et2Zn or R3Al) to cyclic and acyclic enones are quantitatively trapped as enolacetates with acetic anhydride. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7408 / 7412
页数:5
相关论文
共 50 条
  • [1] Tandem asymmetric conjugate addition-silylation of enantiomerically enriched zinc enolates. Synthetic importance and mechanistic implications
    Knopff, O
    Alexakis, A
    ORGANIC LETTERS, 2002, 4 (22) : 3835 - 3837
  • [2] First Tandem Asymmetric Conjugate Addition of Alkenyl Nucleophiles and Silyl Trapping of the Intermediate Enolates
    Westmeier, Johannes
    Pfaff, Christopher
    Siewert, Juergen
    von Zezschwitz, Paultheo
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (13) : 2651 - 2658
  • [3] One-pot asymmetric conjugate addition-trapping of zinc enolates by activated electrophiles
    Rathgeb, Xavier
    March, Sebastien
    Alexakis, Alexandre
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (15): : 5737 - 5742
  • [4] Asymmetric intramolecular conjugate addition of chiral enolates via nonequilibrium
    Monguchi, Daiki
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2006, 126 (08): : 617 - 627
  • [5] Enolates ambushed-asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles
    Kisszekelyi, Peter
    Sebesta, Radovan
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2023, 19 : 593 - 634
  • [6] ASYMMETRIC CONJUGATE ADDITION OF COPPER AZAENOLATES AS SYNTHETIC EQUIVALENT OF ENOLATES TO CYCLIC ENONES
    YAMAMOTO, K
    IIJIMA, M
    OGIMURA, Y
    TETRAHEDRON LETTERS, 1982, 23 (36) : 3711 - 3714
  • [7] Asymmetric Tandem Conjugate Addition and Reaction with Carbocations on Unsaturated Heterocycles
    Mudrakova, Brigita
    Kisszekelyi, Peter
    Vargova, Denisa
    Zakiewicz, Dorota
    Sebesta, Radovan
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (07) : 1337 - 1344
  • [8] (S,S)-(+)-Pseudoephedrine as chiral auxiliary in asymmetric conjugate addition and tandem conjugate addition/α-alkylation reactions
    Reyes, Efraim
    Vicario, Jose L.
    Carrillo, Luisa
    Badia, Dolores
    Uria, Uxue
    Iza, Ainara
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (20): : 7763 - 7772
  • [9] Asymmetric reductive cyclization using the intramolecular conjugate addition of enolates onto α,β-unsaturated sulfoxides
    Yoshizaki, H
    Tanaka, T
    Yoshii, E
    Koizumi, T
    Takeda, K
    TETRAHEDRON LETTERS, 1998, 39 (1-2) : 47 - 50
  • [10] Tandem one pot asymmetric conjugate addition-vinyl triflate formation cross coupling methodology
    Suárez, RM
    Peña, D
    Minnaard, AJ
    Feringa, BL
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (05) : 729 - 731