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
  • [31] A Synthetic Route to Highly Substituted 1,2,3,4-Tetrahydroisoquinolines via Yb(OTf)3-Catalyzed Diastereoselective Ring Opening of Bridged Oxazolidines: Asymmetric Synthesis of 2-Azapodophyllotoxin
    Srivastava, Ajay Kumar
    Koh, Minseob
    Park, Seung Bum
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (17) : 4905 - 4913
  • [32] An Yb(OTf)3-catalyzed, convergent synthesis of new pyranyl- and chromenyl-substituted quinolines through an eco-friendly approach
    Kumarasamy, Chandraprakash
    Sundarasamy, Amsaveni
    Mathan, Sankaran
    Chokkalingam, Uvarani
    Athar, Ata
    Subramaniam, Mohan Palathurai
    Thangaraj, Suresh
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (11) : 2986 - 2992
  • [33] In(OTf)3-catalyzed formal (4+3) cycloaddition reactions of 3-benzylideneindoline-2-thiones with 2-indolylmethanols
    Wang, Xue-Long
    Yang, Yi
    Jiang, Yan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (29) : 5902 - 5906
  • [34] STUDY ON CLAISEN REARRANGEMENT .2. CATALYTIC EFFECT OF ZINC-CHLORIDE ON CLAISEN REARRANGEMENT OF ALLYL [ORTHO-SUBSTITUTED OR PARA-SUBSTITUTED PHENYL] ETHERS
    HAYASHI, T
    GOTO, M
    NIPPON KAGAKU KAISHI, 1978, (07) : 1007 - 1012
  • [35] Y(OTf)3-catalyzed, one-pot synthesis of 1,2,4-oxadiazole derivatives
    Yu, Chuanming
    Lei, Min
    Su, Weike
    Xie, Yuanyuan
    SYNTHETIC COMMUNICATIONS, 2007, 37 (22-24) : 4439 - 4452
  • [36] Cu(OTf)2-catalyzed Et3SiH-reductive etherification of various carbonyl compounds with trimethylsilyl ethers
    Yang, WC
    Lu, XA
    Kulkarni, SS
    Hung, SC
    TETRAHEDRON LETTERS, 2003, 44 (42) : 7837 - 7840
  • [37] Efficient trans-selectivity in the cyclocondensation of (S)-2-[2-(p- tolylsulfinyl) phenyl] acetaldehyde with activated dienes catalyzed by Yb(OTf)3
    Ruano, Jose L. Garcia
    Fernandez-Ibanez, M. Angeles
    Maestro, M. Carmen
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (20): : 7683 - 7689
  • [38] ORTHO-CLAISEN REARRANGEMENT .2. REARRANGEMENT OF CIS- AND TRANS-GAMMA-SUBSTITUTED ALLYL ARYL ETHERS
    WHITE, WN
    NORCROSS, BE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (08) : 1968 - &
  • [39] CLAISEN REARRANGEMENT OF 2-PROPINYL (3-PYRIDYL) AND ALLYL (3-PYRIDYL)ETHERS
    BRUHN, J
    ZSINDELY, J
    SCHMID, H
    HELVETICA CHIMICA ACTA, 1978, 61 (07) : 2542 - 2559
  • [40] Sc(OTf)3-catalyzed [3+2]-cycloaddition of aziridines with nitriles under solvent-free conditions
    Wu, J
    Sun, XY
    Xia, HG
    TETRAHEDRON LETTERS, 2006, 47 (10) : 1509 - 1512
12345