Helicene-like chiral auxiliaries in asymmetric catalysis

被引:142
作者
Aillard, P. [1 ]
Voituriez, A. [1 ]
Marinetti, A. [1 ]
机构
[1] CNRS UPR 2301 1, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
ONE HUNDRED YEARS; PYRIDINE N-OXIDES; ENANTIOSELECTIVE CYCLOISOMERIZATION; STEREOSELECTIVE SYNTHESES; PHOTOPHYSICAL PROPERTIES; KINETIC RESOLUTION; LIGANDS; PHOSPHORUS; COMPLEXES; UNITS;
D O I
10.1039/c4dt01935k
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
This literature overview demonstrates that helically chiral ligands and organocatalysts have been largely neglected so far. However, a few recent studies on helical pyridine, the corresponding ammonium salts and N-oxides have highlighted the significant potential of these compounds as organocatalysts for Michael type additions, aldehyde propargylations, epoxide openings, and others. In addition, helicenes displaying a fused phosphole ring at the end of their polyaromatic structures, have been used as ligands in enantioselective gold promoted cycloisomerization reactions, giving both excellent catalytic activity and high enantiomeric excesses. These recent results are expected to stimulate further research on the catalytic applications of helically chiral auxiliaries in the next few years.
引用
收藏
页码:15263 / 15278
页数:16
相关论文
共 76 条
  • [1] Phosphathiahelicenes: Synthesis and Uses in Enantioselective Gold Catalysis
    Aillard, Paul
    Voituriez, Arnaud
    Dova, Davide
    Cauteruccio, Silvia
    Licandro, Emanuela
    Marinetti, Angela
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (39) : 12373 - 12376
  • [2] A [2+2+2] cyclization strategy for the synthesis of phosphorus embedding [6]helicene-like structures
    Aillard, Paul
    Retailleau, Pascal
    Voituriez, Arnaud
    Marinetti, Angela
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (17) : 2199 - 2201
  • [3] Synthesis and characterization of new hexahelicene derivatives
    Aloui, Faouzi
    El Abed, Riadh
    Marinetti, Angela
    Ben Hassine, Bechir
    [J]. TETRAHEDRON LETTERS, 2007, 48 (11) : 2017 - 2020
  • [4] Synthesis and characterisation of a new helically chiral ruthenium complex
    Aloui, Faouzi
    Moussa, Souad
    Ben Hassine, Bechir
    [J]. TETRAHEDRON LETTERS, 2011, 52 (05) : 572 - 575
  • [5] BENHASSINE B, 1987, B SOC CHIM BELG, V96, P801
  • [6] BENHASSINE B, 1985, B SOC CHIM BELG, V94, P759
  • [7] BENHASSINE B, 1986, B SOC CHIM BELG, V95, P557
  • [8] BENHASSINE B, 1986, B SOC CHIM BELG, V95, P547
  • [9] BENHASSINE B, 1985, B SOC CHIM BELG, V94, P597
  • [10] Benzotetramisole: A remarkably enantioselective acyl transfer catalyst
    Birman, VB
    Li, XM
    [J]. ORGANIC LETTERS, 2006, 8 (07) : 1351 - 1354