Mild and highly chemoselective oxidation of thioethers mediated by Sc(OTf)3

被引：101
作者：
Matteucci, M
Bhalay, G
Bradley, M [1 ]
机构：
[1] Univ Southampton, Dept Chem, Combinatorial Ctr Excellence, Southampton SO17 1BJ, Hants, England
[2] Novartis Pharmaceut, Horsham RH12 5AB, W Sussex, England
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 03期
关键词：
D O I：
10.1021/ol026947i
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Catalytic Sc(OTf)(3) greatly increases the efficiency of hydrogen peroxide mediated monooxidation of alkyl-aryl sulfides and methyl cysteine containing peptides. The method is high yielding, compatible with many widely used protecting groups, suitable for solid-phase applications and proceeds with minimum over-oxidation.
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页码：235 / 237
页数：3
相关论文
共 21 条
  • [1] New ligands for manganese catalysed selective oxidation of sulfides to sulfoxides with hydrogen peroxide
    Brinksma, J
    La Crois, R
    Feringa, BL
    Donnoli, MI
    Rosini, C
    [J]. TETRAHEDRON LETTERS, 2001, 42 (24) : 4049 - 4052
  • [2] Burrage S, 2000, CHEM-EUR J, V6, P1455, DOI 10.1002/(SICI)1521-3765(20000417)6:8<1455::AID-CHEM1455>3.3.CO
  • [3] 2-D
  • [4] A highly efficient route to dehydroalanine containing peptides
    Burrage, SA
    Raynham, T
    Bradley, M
    [J]. TETRAHEDRON LETTERS, 1998, 39 (18) : 2831 - 2834
  • [5] Selective oxidation of allylic sulfides by hydrogen peroxide with the trirutile-type solid oxide catalyst LiNbMoO6
    Choi, S
    Yang, JD
    Ji, M
    Choi, H
    Kee, M
    Ahn, KH
    Byeon, SH
    Baik, W
    Koo, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) : 8192 - 8198
  • [6] Introduction: Frontiers in lanthanide chemistry
    Kagan, HB
    [J]. CHEMICAL REVIEWS, 2002, 102 (06) : 1805 - 1806
  • [7] Kobayashi S, 1999, EUR J ORG CHEM, V1999, P15
  • [8] KOBAYASHI S, 1999, LANTHANIDES CHEM USE
  • [9] SYNTHESIS OF SULFOXIDES BY OXIDATION OF THIOETHERS
    MADESCLAIRE, M
    [J]. TETRAHEDRON, 1986, 42 (20) : 5459 - 5495
  • [10] Phosphodiester cleavage by yttrium(III) peroxide complexes
    Mejia-Radillo, Y
    Yatsimirsky, AK
    [J]. INORGANICA CHIMICA ACTA, 2002, 328 : 241 - 246
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