The Allylic Alkylation of Ketone Enolates

被引:17
|
作者
Junk, Lukas [1 ]
Kazmaier, Uli [1 ]
机构
[1] Saarland Univ, Organ Chem 1, Campus C4-2, D-66123 Saarbrucken, Germany
来源
CHEMISTRYOPEN | 2020年 / 9卷 / 09期
关键词
allylic alkylations; enolates; ketones; palladium; transition metals; CATALYZED DECARBOXYLATIVE ALLYLATION; ENANTIOSELECTIVE TOTAL-SYNTHESIS; TRANSITION-METAL CATALYSIS; FORMAL SYNTHESIS; ASYMMETRIC ALKYLATION; CONJUGATE ADDITION; VINYLOGOUS ESTERS; ALPHA-ALLYLATION; INNER-SPHERE; PALLADIUM;
D O I
10.1002/open.202000175
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The palladium-catalyzed allylic alkylation of non-stabilized ketone enolates was thought for a long time to be not as efficient as the analogous reactions of stabilized enolates, e. g. of malonates and beta-ketoesters. The field has experienced a rapid development during the last two decades, with a range of new, highly efficient protocols evolved. In this review, the early developments as well as current methods and applications of palladium-catalyzed ketone enolate allylations will be discussed.
引用
收藏
页码:929 / 952
页数:24
相关论文
共 50 条
  • [21] Nickel-Catalyzed Alkylation of Ketone Enolates: Synthesis of Monoselective Linear Ketones
    Das, Jagadish
    Vellakkaran, Mari
    Banerjee, Debasis
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (02): : 769 - 779
  • [22] Highly efficient ligands for palladium-catalyzed asymmetric alkylation of ketone enolates
    You, SL
    Hou, XL
    Dai, LX
    Zhu, XZ
    ORGANIC LETTERS, 2001, 3 (02) : 149 - 151
  • [23] Enantioselective synthesis of α-tertiary hydroxyaldehydes by palladium-catalyzed asymmetric allylic alkylation of enolates
    Trost, Barry M.
    Xu, Jiayi
    Reichle, Markus
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (02) : 282 - 283
  • [24] Allylic alkylation versus Michael induced ring closure: Chelated enolates as versatile nucleophiles
    Pohlman, M
    Kazmaier, U
    Lindner, T
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20): : 6909 - 6912
  • [25] The Catalytic Asymmetric Allylic Alkylation of Acyclic Enolates for the Construction of Quaternary and Tetrasubstituted Stereogenic Centres
    Griffiths, Connor M.
    Franckevicius, Vilius
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (20)
  • [26] Iridium-Catalyzed Enantioselective Allylic Substitution of Unstabilized Enolates Derived from α,β-Unsaturated Ketone
    Chen, Ming
    Hartwig, John F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (33) : 8691 - 8695
  • [27] On the distribution of the alkylation of enolates
    Adickes, F
    von Hessling, G
    von Mullenheim, S
    BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1933, 66 : 826 - 828
  • [28] Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres
    Nairoukh, Zackaria
    Kumar, Gunda G. K. S. Narayana
    Minko, Yury
    Marek, Ilan
    CHEMICAL SCIENCE, 2017, 8 (01) : 627 - 630
  • [29] Iridium-Catalyzed Diastereo-, Enantio-, and Regioselective Allylic Alkylation with Prochiral Enolates
    Hethcox, J. Caleb
    Shockley, Samantha E.
    Stoltz, Brian M.
    ACS CATALYSIS, 2016, 6 (09): : 6207 - 6213
  • [30] ALKYLATION OF ENOLATES WITH TRIFLATES
    BATES, RB
    TAYLOR, SR
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16): : 4469 - 4470