Enantioselective Copper-Catalyzed Conjugate Addition of Trimethylaluminium to β,γ-Unsaturated α-Ketoesters

被引：80
作者：
Gremaud, Ludovic [1 ]
Alexakis, Alexandre [1 ]
机构：
[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 03期
基金：
新加坡国家研究基金会;
关键词：
amino acids; asymmetric catalysis; copper; enantioselectivity; synthetic methods; CYCLIC 1,3-DICARBONYL COMPOUNDS; ASYMMETRIC MICHAEL REACTIONS; PRIMARY ALLYLIC ALCOHOLS; KETO ESTERS; TRIALKYLALUMINUM REAGENTS; GRIGNARD-REAGENTS; ACID; 1,4-ADDITION; ENONES; ISOMERIZATION;
D O I：
10.1002/anie.201107324
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Not a cop out: The copper-catalyzed asymmetric conjugate addition of organometallic reagents to Michael acceptors is an important methodology for forming a C-C bond in an enantioselective manner. Such an addition of Me 3Al to β,γ-unsaturated α-ketoesters is described to proceed in high yield and selectivity. CuTC=copper(I) thiophene-2-carboxylate. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：794 / 797
页数：4
相关论文
共 50 条
  • [41] Copper-catalyzed Asymmetric Conjugate Addition to Challenging Michael Acceptors and Synthesis of Relevant Target Molecules
    Gremaud, Ludovic
    Palais, Laetitia
    Alexakis, Alexandre
    CHIMIA, 2012, 66 (04) : 196 - 200
  • [42] Enantioselective Copper-Catalyzed Quinoline Alkynylation
    Pappoppula, Mukesh
    Cardoso, Flavio S. P.
    Garrett, B. Owen
    Aponick, Aaron
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (50) : 15202 - 15206
  • [43] Enantioselective Intramolecular Copper-Catalyzed Borylacylation
    Whyte, Andrew
    Burton, Katherine I.
    Zhang, Jingli
    Lautens, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (42) : 13927 - 13930
  • [44] Copper-catalyzed Enantioselective Allylic Substitution
    Langlois, Jean-Baptiste
    Alexakis, Alexandre
    TRANSITION METAL CATALYZED ENANTIOSELECTIVE ALLYLIC SUBSTITUTION IN ORGANIC SYNTHESIS, 2012, 38 : 235 - 268
  • [45] Rhodium and copper-catalyzed asymmetric conjugate addition of alkenyl nucleophiles
    Mueller, Daniel
    Alexakis, Alexandre
    CHEMICAL COMMUNICATIONS, 2012, 48 (99) : 12037 - 12049
  • [46] Enantioselective Conjugate Addition Catalyzed by a Copper Phosphoramidite Complex: Computational and Experimental Exploration of Asymmetric Induction
    Ardkhean, Ruchuta
    Roth, Philippe M. C.
    Maksyrnowicz, Rebecca M.
    Curran, Alex
    Peng, Qjan
    Paton, Robert S.
    Fletcher, Stephen P.
    ACS CATALYSIS, 2017, 7 (10): : 6729 - 6737
  • [47] New Bifunctional Substrates for Copper-Catalyzed Asymmetric Conjugate Addition Reactions with Trialkylaluminium
    Ladjel, Chehla
    Fuchs, Nicolas
    Zhao, Jinkai
    Bernardinelli, Gerald
    Alexakis, Alexandre
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (29) : 4949 - 4955
  • [48] Copper-catalyzed asymmetric 1,4-conjugate addition of dialkylzinc to enones
    Gou, Shaohua
    Ye, Zhongbin
    Shi, Leiting
    Qing, Dayong
    Zhang, Wen
    Wang, Yuliang
    APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (07) : 517 - 522
  • [49] Peptidic amidomonophosphane ligand for copper-catalyzed asymmetric conjugate addition of diorganozincs to cycloalkenones
    Soeta, Takahiro
    Selim, Khalid
    Kuriyama, Masami
    Tomioka, Kiyoshi
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (4-5) : 629 - 635
  • [50] Recent Advances in Copper-Catalyzed Silyl Addition of Unsaturated Compounds
    Han Biao
    Li Weishuang
    Chen Shuhan
    Zhang Zelang
    Zhao Xue
    Zhang Yaoyao
    Zhu Lei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (02) : 555 - 572
12345