The Cu(OTf)2- and Yb(OTf)3-catalyzed Claisen rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ethers

被引：37
|
作者：
Hiersemann, M [1 ]
Abraham, L [1 ]
机构：
[1] Tech Univ Dresden, Inst Organ Chem, D-01062 Dresden, Germany
来源：
ORGANIC LETTERS | 2001年 / 3卷 / 01期
关键词：
D O I：
10.1021/ol006760w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] The Cu(OTf)(2)- and Yb(OTf)(3)-catalyzed Claisen rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ethers has been developed. Reactivity and stereoselectivity strongly depend on the substrate structure.
引用
收藏
页码：49 / 52
页数：4
相关论文
共 50 条
  • [1] Diastereoselective bismuth triflate catalyzed Claisen rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ethers
    Ollevier, Thierry
    Mwene-Mbeja, Topwe M.
    CANADIAN JOURNAL OF CHEMISTRY, 2008, 86 (03) : 209 - 212
  • [2] The Pd(II)-catalyzed and the thermal Claisen rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ethers
    Hiersemann, M
    SYNLETT, 1999, (11) : 1823 - 1825
  • [3] Highly enantioselective catalytic asymmetric Claisen rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ethers
    Abraham, L
    Körner, M
    Hiersemann, M
    TETRAHEDRON LETTERS, 2004, 45 (18) : 3647 - 3650
  • [4] The catalytic diastereo- and enantioselective Claisen rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ether
    Abraham, L
    Körner, M
    Schwab, P
    Hiersemann, M
    ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (11) : 1281 - 1294
  • [5] Yb(OTf)3-catalyzed [4+2] cycloaddition of allenyltrimethylsilylthioketenes with arylaldimines
    Aoyagi, Shigenobu
    Ohata, Satoru
    Shimada, Kazuaki
    Takikawa, Yuji
    SYNLETT, 2007, (04) : 615 - 618
  • [6] Synthesis and Lewis acid catalyzed Claisen rearrangement of 2-(1,3-oxazolin-2-yl)-substituted allyl vinyl ethers
    Helmboldt, H
    Hiersemann, M
    TETRAHEDRON, 2003, 59 (23) : 4031 - 4038
  • [7] Yb(OTf)3 and ZrCl4 mediated rearrangement of alkoxybenzyl allyl ethers into aldehydes
    Krishna, PR
    Reddy, CG
    Sharma, GVM
    LETTERS IN ORGANIC CHEMISTRY, 2004, 1 (03) : 212 - 214
  • [8] Sc(OTf)3-catalyzed [3+2]-cycloaddition of nitrones with ynones
    He, Chun-Ting
    Han, Xiao-Li
    Zhang, Yan-Xue
    Du, Zhen-Ting
    Si, Chang-Mei
    Wei, Bang-Guo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (02) : 457 - 466
  • [9] CLAISEN REARRANGEMENT OF 1-SUBSTITUTED 2-NAPHTHYL ALLYL ETHERS
    GREEN, J
    MCHALE, D
    CHEMISTRY & INDUSTRY, 1964, (43) : 1801 - 1802
  • [10] Enantioselective aromatic Claisen rearrangement of allyl 2-naphthyl ethers catalyzed by π-Cu(ii) complexes
    Yao, Lu
    Takeda, Kazuki
    Ando, Kaori
    Ishihara, Kazuaki
    CHEMICAL SCIENCE, 2023, 14 (09) : 2441 - 2446
12345