Catalytic asymmetric conjugate addition of Grignard reagents to chromones

被引:51
|
作者
Vila, Carlos [1 ]
Hornillos, Valentin [1 ]
Fananas-Mastral, Martin [1 ]
Feringa, Ben L. [1 ]
机构
[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
关键词
PHOSPHINE-PHOSPHITE LIGANDS; 2-SUBSTITUTED CHROMAN-4-ONES; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; CHROMANONES; COMPLEXES; ENONES; 1,4-ADDITION; CONSTRUCTION; FLAVANONES;
D O I
10.1039/c3cc43105c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly regio- and enantioselective copper catalysed direct conjugate addition of Grignard reagents to chromones has been developed taking advantage of the reduced reactivity of the resulting magnesium enolates. This methodology tolerates a broad scope of alkyl Grignards including secondary alkyl magnesium reagents as well as functionalised chromones.
引用
收藏
页码:5933 / 5935
页数:3
相关论文
共 50 条
  • [31] Asymmetric amplification in the catalytic enantioselective 1,2-addition of Grignard reagents to enones
    Caprioli, Francesca
    Madduri, Ashoka V. R.
    Minnaard, Adriaan J.
    Harutyunyan, Syuzanna R.
    CHEMICAL COMMUNICATIONS, 2013, 49 (48) : 5450 - 5452
  • [32] A Convenient Catalytic Asymmetric Conjugate Addition Reaction to Enones Using Alkylzirconium Reagents
    Maksymowicz, Rebecca M.
    Sidera, Mireia
    Roth, Philippe M. C.
    Fletcher, Stephen P.
    SYNTHESIS-STUTTGART, 2013, 45 (19): : 2662 - 2668
  • [33] ASYMMETRIC INDUCTION IN THE ADDITION OF GRIGNARD-REAGENTS TO NITRONES
    COWLING, MP
    JENKINS, PR
    COOPER, K
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (22) : 1503 - 1504
  • [34] Unsaturated nitriles: Conjugate addition-silylation with Grignard reagents
    Fleming, FF
    Pu, YF
    Tercek, F
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14): : 4883 - 4885
  • [35] CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO SUBSTITUTED ISOPROPYLIDENE METHYLENEMALONATES
    HASLEGO, ML
    SMITH, FX
    SYNTHETIC COMMUNICATIONS, 1980, 10 (06) : 421 - 427
  • [36] Unsaturated Nitriles: Conjugate Addition-Silylation with Grignard Reagents
    Fleming, F. F.
    Pu, Y.
    Tercek, F.
    Journal of Organic Chemistry, 62 (14):
  • [37] Catalytic asymmetric addition of Grignard reagents to alkenyl-substituted aromatic N-heterocycles
    Jumde, Ravindra P.
    Lanza, Francesco
    Veenstra, Marieke J.
    Harutyunyan, Syuzanna R.
    SCIENCE, 2016, 352 (6284) : 433 - 437
  • [38] Catalytic Enantioselective Addition of Aryl Grignard Reagents to Ketones
    Fernandez-Mateos, Emilio
    Macia, Beatriz
    Yus, Miguel
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (29) : 6519 - 6526
  • [39] Asymmetric One-Pot Conjugate Addition of Grignard Reagents to α,β-Unsaturated Compounds Followed by Reaction with Carbenium Ions
    Drusan, Michal
    Rakovsky, Erik
    Marek, Jaromir
    Sebesta, Radovan
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (07) : 1493 - 1498
  • [40] Recent progress in asymmetric 1,4-conjugate addition of Grignard reagents catalyzed by copper-complex
    Wang, Shun-Yi
    Ji, Shun-Jun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (02) : 181 - 186