Polystyrenes with chiral phosphoramide substituents as Lewis base catalysts for asymmetric addition of allyltrichlorosilane: enhancement of catalytic performance by polymer effect.

Department of Advanced Materials Chemistry, Faculty of Engineering, Yokohama National University, 79-5 Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan.
Chemical Communications (Impact Factor: 6.72). 05/2005; DOI: 10.1039/b417311b
Source: PubMed

ABSTRACT In the asymmetric addition of allyltrichlorosilane to benzaldehyde, polystyrenes with chiral phosphoramide substituents as Lewis base catalysts showed up to 2.4 times better catalytic activity and 1.4 times higher enantioselectivity than the corresponding low-molecular-weight analogues.

  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: This review is intended to update the impressive amount of recent developments of asymmetric organocatalysis in numerous reaction types, such as nucleophilic additions to electron-deficient CC double bonds, nucleophilic additions to CO double bonds, nucleophilic additions to CN double bonds, nucleophilic additions to unsaturated nitrogen, nucleophilic substitutions at aliphatic carbon, cycloaddition reactions, oxidations, reductions, kinetic resolutions and miscellaneous reactions, covering the literature from 2005 to 2007. This review clearly demonstrates the explosive growth and power of this new field of organic chemistry, which has become, in the last few years, the third methodology of asymmetric catalysis besides organometallic and enzymatic catalysis.Figure optionsView in workspaceDownload full-size imageDownload as PowerPoint slide
    ChemInform 09/2007; 63(38):9267–9331.
  • [Show abstract] [Hide abstract]
    ABSTRACT: A pyridine unit with a conformationally rigid chiral backbone has been designed and synthesized in an enantiomerically pure form to utilize in the Lewis base-catalyzed Sakurai–Hosomi–Denmark-type allylation reaction. The chiral pyridine N-oxide in 1:1 mixture of chloroform and 1,1,2,2-tetrachloroethane produced the homoallylic alcohols in up to 98% yield and up to 94% ee.
    Advanced Synthesis & Catalysis 07/2012; 354:2101. · 5.54 Impact Factor
  • Catalytic Methods in Asymmetric Synthesis: Advanced Materials, Techniques, and Applications, 07/2011: pages 83 - 175; , ISBN: 9781118087992