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
  • [11] Platinum(II) Catalysts for Highly Enantioselective 1,6-Enyne Cycloisomerizations. Synthetic, Structural, and Catalytic Studies
    Brissy, Delphine
    Skander, Myriem
    Jullien, Helene
    Retailleau, Pascal
    Marinetti, Angela
    [J]. ORGANIC LETTERS, 2009, 11 (10) : 2137 - 2139
  • [12] Synthesis, Characterisation, and Organocatalytic Activity of Chiral Tetrathiahelicene Diphosphine Oxides
    Cauteruccio, Silvia
    Dova, Davide
    Benaglia, Maurizio
    Genoni, Andrea
    Orlandi, Manuel
    Licandro, Emanuela
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (13) : 2694 - 2702
  • [13] Gold(I) Complexes of Tetrathiaheterohelicene Phosphanes
    Cauteruccio, Silvia
    Loos, Annette
    Bossi, Alberto
    Jaimes, Maria Camila Blanco
    Dova, Davide
    Rominger, Frank
    Prager, Stefan
    Dreuw, Andreas
    Licandro, Emanuela
    Hashmi, A. Stephen K.
    [J]. INORGANIC CHEMISTRY, 2013, 52 (14) : 7995 - 8004
  • [14] Helical Chiral 2,2′-Bipyridine N- Monoxides as Catalysts in the Enantioselective Propargylation of Aldehydes with Allenyltrichlorosilane
    Chen, Jinshui
    Captain, Burjor
    Takenaka, Norito
    [J]. ORGANIC LETTERS, 2011, 13 (07) : 1654 - 1657
  • [15] Helical Chiral Pyridine N-Oxides: A New Family of Asymmetric Catalysts
    Chen, Jinshui
    Takenaka, Norito
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (30) : 7268 - 7276
  • [16] Crassous J., 2014, CHEM SCI, DOI [10.1039/C4SC01404A, DOI 10.1039/C4SC01404A]
  • [17] Point-to-helical chirality transfer for a scalable and resolution-free synthesis of a helicenoidal DMAP organocatalyst
    Crittall, Matthew R.
    Fairhurst, Nathan W. G.
    Carbery, David R.
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (91) : 11181 - 11183
  • [18] Design, Synthesis, and Evaluation of a Helicenoidal DMAP Lewis Base Catalyst
    Crittall, Matthew R.
    Rzepa, Henry S.
    Carbery, David R.
    [J]. ORGANIC LETTERS, 2011, 13 (05) : 1250 - 1253
  • [19] Lewis base catalysis in organic synthesis
    Denmark, Scott E.
    Beutner, Gregory L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) : 1560 - 1638
  • [20] DINAPHTHO[2,1-B-1',2'-D]PHOSPHOLES - A NEW CLASS OF ATROPISOMERIC PHOSPHORUS LIGANDS
    DORE, A
    FABBRI, D
    GLADIALI, S
    DELUCCHI, O
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (14) : 1124 - 1125