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
  • [21] Protonation-Assisted Conjugate Addition of Axially Chiral Enolates: Asymmetric Synthesis of Multisubstituted β-Lactams from α-Amino Acids
    Yoshimura, Tomoyuki
    Takuwa, Masatoshi
    Tomohara, Keisuke
    Uyama, Makoto
    Hayashi, Kazuhiro
    Yang, Pan
    Hyakutake, Ryuichi
    Sasamori, Takahiro
    Tokitoh, Norihiro
    Kawabata, Takeo
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (48) : 15330 - 15336
  • [22] ASYMMETRIC-SYNTHESIS OF DIBENZYLBUTYROLACTONES AND ARYLTETRALIN LIGNAN LACTONES BY TANDEM CONJUGATE ADDITION TO A CHIRAL BUTENOLIDE
    PELTER, A
    WARD, RS
    JONES, DM
    MADDOCKS, P
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (21): : 2621 - 2629
  • [23] ASYMMETRIC INTRAMOLECULAR CONJUGATE ADDITION OF α-AMINO ACID DERIVATIVES VIA RACEMIZATION-FREE EQUILIBRIUM OF INTERMEDIARY CHIRAL ENOLATES
    Monguchi, Daiki
    Yoshimura, Tomoyuki
    Irie, Kazuyuki
    Hayashi, Kazuhiro
    Majumdar, Swapan
    Sasamori, Takahiro
    Tokitoh, Norihiro
    Kawabata, Takeo
    HETEROCYCLES, 2012, 86 (02) : 1483 - 1494
  • [24] Metal-catalyzed asymmetric conjugate addition reaction: formation of quaternary stereocenters
    Hawner, Christine
    Alexakis, Alexandre
    CHEMICAL COMMUNICATIONS, 2010, 46 (39) : 7295 - 7306
  • [25] Formation of highly substituted chiral cyclohexanone derivatives using a tandem conjugate addition/cyclisation
    Jeffery, DW
    Perkins, MV
    TETRAHEDRON LETTERS, 2004, 45 (47) : 8667 - 8671
  • [26] Epoxysilane rearrangement induced by a carbanion generated by conjugate addition of enolates of chloroacetate and α-chloroacetamides:: Formation of functionalized cyclopropane derivatives
    Okamoto, N
    Sasaki, M
    Kawahata, M
    Yamaguchi, K
    Takeda, K
    ORGANIC LETTERS, 2006, 8 (09) : 1889 - 1891
  • [27] Asymmetric Synthesis of Multisubstituted Dihydrobenzofurans by Intramolecular Conjugate Addition of Short-Lived C-O Axially Chiral Enolates
    Tomohara, Keisuke
    Kasamatsu, Koji
    Yoshimura, Tomoyuki
    Furuta, Takumi
    Kawabata, Takeo
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2016, 64 (07) : 899 - 906
  • [28] Asymmetric Synthesis of Multi-substituted β-Lactams via C-N Axially Chiral Enolates in Intramolecular Conjugate Addition
    Yoshimura, Tomoyuki
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2012, 132 (11): : 1287 - 1295
  • [29] Copper catalyzed tandem asymmetric conjugate addition-cyclization reaction in the presence of chiral phosphoramidite ligands
    Li, KY
    Alexakis, A
    TETRAHEDRON LETTERS, 2005, 46 (46) : 8019 - 8022
  • [30] Asymmetric tandem conjugate addition-allylation of chiral (p-tolylsulfinyl)pyrrolyl cinnamoyl amide
    Arai, Y
    Kasai, M
    Ueda, K
    Masaki, Y
    SYNTHESIS-STUTTGART, 2003, (10): : 1511 - 1516