Catalytic enantioselective addition of organoaluminum reagents to aldehydes

被引:26
|
作者
Fernandez-Mateos, Emilio
Macia, Beatriz [1 ]
Yus, Miguel
机构
[1] Univ Alicante, Dept Quim Organ, E-03080 Alicante, Spain
关键词
GRIGNARD-REAGENTS; ASYMMETRIC HYDROSILYLATION; TRIALKYLALUMINUM ADDITION; DIORGANOZINC REAGENTS; CARBONYL-COMPOUNDS; KETONES; HYDROGENATION; COMPLEXES; ALKYLATION; REDUCTION;
D O I
10.1016/j.tetasy.2012.05.007
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An efficient catalyst for the asymmetric addition of organoaluminum reagents to aldehydes is presented. The system is based on a readily available binaphthyl derivative as a chiral ligand and an excess of titanium tetraisopropoxide. The asymmetric methylation, ethylation, and propylation of a wide variety of aromatic and aliphatic aldehydes proceeded with good yields and with high enantioselectivities in a simple one-pot procedure under mild conditions. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:789 / 794
页数:6
相关论文
共 50 条
  • [1] Catalytic Enantioselective Addition of Organozirconium Reagents to Aldehydes
    Sola, Ricard
    Veguillas, Marcos
    Gonzalez-Soria, Maria Jose
    Carter, Nicholas
    Fernandez-Ibanez, M. Angeles
    Macia, Beatriz
    [J]. MOLECULES, 2018, 23 (04):
  • [2] Catalytic Enantioselective Addition of Alkylzirconium Reagents to Aliphatic Aldehydes
    Vaccari, Jade
    Gonzalez-Soria, Maria Jose
    Carter, Nicholas
    Macia, Beatriz
    [J]. MOLECULES, 2021, 26 (15):
  • [3] Catalytic Enantioselective Addition of Alkyl Grignard Reagents to Aliphatic Aldehydes
    Fernandez-Mateos, Emilio
    Macia, Beatriz
    Yus, Miguel
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (07) : 1249 - 1254
  • [4] Catalytic Enantioselective Addition of MeMgBr and Other Grignard Reagents to Aldehydes
    Fernandez-Mateos, Emilio
    Macia, Beatriz
    Ramon, Diego J.
    Yus, Miguel
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (34) : 6851 - 6855
  • [5] Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones
    Denmark, SE
    Fu, JP
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2763 - 2793
  • [6] α-Hydroxy carboxylic acids as ligands for enantioselective addition reactions of organoaluminum reagents to aromatic and aliphatic aldehydes
    Bauer, T
    Gaiewiak, J
    [J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (04) : 851 - 855
  • [7] ENANTIOSELECTIVE ADDITION OF ORGANOZINC REAGENTS TO ALDEHYDES
    SOAI, K
    NIWA, S
    [J]. CHEMICAL REVIEWS, 1992, 92 (05) : 833 - 856
  • [8] Enantioselective addition of Grignard reagents to aldehydes
    Englebienne, P
    Schulz, H
    Nudelman, N
    [J]. MOLECULES, 2000, 5 (03) : 598 - 599
  • [9] Catalytic enantioselective addition of methyltriisopropoxititanium to aldehydes
    Veguillas, Marcos
    Sola, Ricard
    Fernandez-Ibanez, M. Angeles
    Macia, Beatriz
    [J]. TETRAHEDRON-ASYMMETRY, 2016, 27 (14-15) : 643 - 648
  • [10] Functionalized organolithium reagents in the synthesis of chiral ligands for catalytic enantioselective addition of diethylzinc to aldehydes
    Dobrikov, Georgi M.
    Philipova, Irena
    Nikolova, Rositsa
    Shivachev, Boris
    Chimov, Angel
    Dimitrov, Vladimir
    [J]. POLYHEDRON, 2012, 45 (01) : 126 - 143