Bi(OTf)3 and SiO2-Bi(OTf)3 as effective catalysts for the Ferrier rearrangement

被引:53
作者
Babu, JL
Khare, A
Vankar, YD [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
[2] Univ Lucknow, Dept Chem, Lucknow 226006, Uttar Pradesh, India
来源
MOLECULES | 2005年 / 10卷 / 08期
关键词
glycals; pseudoglycals; glycosidation; bismuth triflate; Ferrier rearrangement;
D O I
10.3390/10080884
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Bi(OTf)(3) and SiO2-Bi(OTf)(3) are found to effectively catalyze the Ferrier rearrangement of tri-O-acetyl glycals with different alcohols providing an effective route to 2,3-unsaturated O-glycosides with good anomeric selectivity and good to excellent yields after short reaction times.
引用
收藏
页码:884 / 892
页数:9
相关论文
共 41 条
  • [21] Metal-catalyzed transformation of D-glucal to optically active furan diol
    Hayashi, M
    Kawabata, H
    Yamada, K
    [J]. CHEMICAL COMMUNICATIONS, 1999, (11) : 965 - 966
  • [22] KLAFFKE W, 1991, LIEBIGS ANN CHEM, P509
  • [23] KOREEDA M, 1995, SYNLETT, P90
  • [24] An efficient method for the preparation of bismuth(III) trifluoromethanesulfonate
    Labrouillère, M
    Le Roux, C
    Gaspard, H
    Laporterie, A
    Dubac, J
    Desmurs, JR
    [J]. TETRAHEDRON LETTERS, 1999, 40 (02) : 285 - 286
  • [25] Laurent-Robert H, 2000, SYNLETT, P1160
  • [26] LOPEZ JC, 1995, J ORG CHEM, V60, P3851
  • [27] Masson C, 2000, SYNLETT, P1281
  • [28] Orita A, 2000, ANGEW CHEM INT EDIT, V39, P2877, DOI 10.1002/1521-3773(20000818)39:16<2877::AID-ANIE2877>3.0.CO
  • [29] 2-V
  • [30] A practical, cheap and environmentally friendly preparation of bismuth(III) trifluoromethanesulfonate
    Répichet, S
    Zwick, A
    Vendier, L
    Le Roux, C
    Dubac, J
    [J]. TETRAHEDRON LETTERS, 2002, 43 (06) : 993 - 995