Lewis base catalyzed asymmetric reactions involving hypervalent silicate intermediates

被引:123
作者
Orito, Y [1 ]
Nakajima, M [1 ]
机构
[1] Kumamoto Univ, Fac Med & Pharmaceut Sci, Kumamoto 8620973, Japan
来源
SYNTHESIS-STUTTGART | 2006年 / 09期
关键词
asymmetric; organocatalysis; hypervalent silicon; Lewis base; stereoselectivity;
D O I
10.1055/s-2006-926405
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of catalytic enantioselective reactions is a challenging area in synthetic organic chemistry. In the last decade, numerous chiral metal complexes, which act as Lewis acids, have been very successful. However, Lewis base catalyzed asymmetric reactions are also attracting attention. Recent developments in silicon-based chemistry have led to new asymmetric reactions, which involve so-called hypervalent silicates as intermediates, wherein new types of organocatalysts are often utilized as promoters. This review presents the progress in silicate-mediated asymmetric reactions catalyzed by chiral Lewis bases, particularly those based on various types of silicon Compounds.
引用
收藏
页码:1391 / 1401
页数:11
相关论文
共 92 条
  • [61] Role of noncovalent interactions in the enantioselective reduction of aromatic ketimines with trichlorosilane
    Malkov, AV
    Mariani, A
    MacDougall, KN
    Kocovsky, P
    [J]. ORGANIC LETTERS, 2004, 6 (13) : 2253 - 2256
  • [62] New Lewis-basic N-oxides as chiral organocatalysts in asymmetric allylation of aldehydes
    Malkov, AV
    Bell, M
    Orsini, M
    Pernazza, D
    Massa, A
    Herrmann, P
    Meghani, P
    Kocovsky, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (25) : 9659 - 9668
  • [63] Quinox, a quinoline-type N-oxide, as organocatalyst in the asymmetric allylation of aromatic aldehydes with allyltrichlorosilanes:: The role of arene-arene interactions
    Malkov, AV
    Dufková, L
    Farrugia, L
    Kocovsky, P
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) : 3674 - 3677
  • [64] New pyridine-derived N-oxides as chiral organocatalysts in asymmetric allylation of aldehydes
    Malkov, AV
    Bell, M
    Vassieu, M
    Bugatti, V
    Kocovsky, P
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 196 (1-2) : 179 - 186
  • [65] Chiral 2,2′-bipyridine-type N-monoxides as organocatalysts in the enantioselective allylation of aldehydes with allyltrichlorosilane
    Malkov, AV
    Orsini, M
    Pernazza, D
    Muir, KW
    Langer, V
    Meghani, P
    Kocovsky, P
    [J]. ORGANIC LETTERS, 2002, 4 (06) : 1047 - 1049
  • [66] Chiral allylic and allenic stannanes as reagents for asymmetric synthesis
    Marshall, JA
    [J]. CHEMICAL REVIEWS, 1996, 96 (01) : 31 - 47
  • [67] Asymmetric allylation of aldehydes with allyltrichlorosilane promoted by chiral sulfoxides
    Massa, A
    Malkov, AV
    Kocovsky, P
    Scettri, A
    [J]. TETRAHEDRON LETTERS, 2003, 44 (38) : 7179 - 7181
  • [68] Enantioselective ring opening of meso-epoxides with tetrachlorosilane catalyzed by chiral bipyridine N,N'-dioxide derivatives
    Nakajima, M
    Saito, M
    Uemura, M
    Hashimoto, S
    [J]. TETRAHEDRON LETTERS, 2002, 43 (49) : 8827 - 8829
  • [69] Nakajima M, 2000, CHEM PHARM BULL, V48, P306
  • [70] Chiral phosphine oxide BINAPO as a catalyst for enantioselective allylation of aldehydes with allyltrichlorosilanes
    Nakajima, M
    Kotani, S
    Ishizuka, T
    Hashimoto, S
    [J]. TETRAHEDRON LETTERS, 2005, 46 (01) : 157 - 159