A Straightforward Synthesis of 2,3,4,5-Tetrasubstituted Tetrahydrofuran Derivatives

被引:7
|
作者
Aljarilla, Ana [1 ]
Plumet, Joaquin [1 ]
机构
[1] Univ Complutense, Fac Quim, Dept Quim Organ, E-28040 Madrid, Spain
来源
SYNTHESIS-STUTTGART | 2008年 / 21期
关键词
metathesis; tetrahydrofurans; Hoveyda-Grubbs catalyst; oxabicyclic compounds;
D O I
10.1055/s-0028-1083180
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise synthesis of 2,3,4,5-tetrasubstituted tetrahydrofurans starting from furan via 7-oxabicyclo[2.2.1]hept-5-ene-2,3-diol (2,3-dihydroxy-7-oxanorbornene) derivatives is reported. The key step of these transformations was the sequence ring-opening metathesis-cross metathesis (ROM-CM) reactions of the oxabicyclic compounds in the presence of ethylene and using commercially available 2nd generation Hoveyda-Grubbs catalyst.
引用
收藏
页码:3516 / 3524
页数:9
相关论文
共 50 条
  • [21] Molybdate sulfuric acid as a reusable solid catalyst in the synthesis of 2,3,4,5-tetrasubstituted pyrroles via a new one-pot [2+2+1] strategy
    Tamaddon, Fatemeh
    Farahi, Mahnaz
    Karami, Bahador
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2012, 356 : 85 - 89
  • [23] ELECTROCHEMICAL AND SPECTROSCOPIC STUDY ON CATION RADICALS, DICATIONS, NITRENIUM IONS AND PYRRYL RADICALS DERIVED FROM 2,3,4,5-TETRASUBSTITUTED PYRROLES
    GROSSI, PJ
    MARCHETTI, L
    RAMASSEUL, R
    RASSAT, A
    SERVE, D
    JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1978, 87 (03): : 353 - 368
  • [24] HINDERED AMINES - 3,3,5,5-TETRASUBSTITUTED 2-MORPHOLONES AND MORPHOLINES, AND THEIR DERIVATIVES
    LAI, JT
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1983, 186 (AUG): : 65 - ORGN
  • [25] INFRARED-SPECTRA OF 1,2,3,5-TETRASUBSTITUTED BENZENE DERIVATIVES .2.
    VARSANYI, G
    SOHAR, P
    ACTA CHIMICA ACADEMIAE SCIENTARIUM HUNGARICAE, 1973, 76 (03): : 243 - 268
  • [26] INFRARED-SPECTRA OF 1,2,3,5-TETRASUBSTITUTED BENZENE-DERIVATIVES
    VARSANYI, G
    HORVATH, G
    IMRE, L
    SCHAWARTZ, J
    SOHAR, P
    SOTI, F
    ACTA CHIMICA ACADEMIAE SCIENTARIUM HUNGARICAE, 1977, 93 (3-4): : 315 - 355
  • [27] A simple and general synthesis of 2,2,4,5-tetrasubstituted furan-3(2H)-ones
    Kawaguchi, T
    Yasuta, S
    Inoue, Y
    SYNTHESIS-STUTTGART, 1996, (12): : 1431 - &
  • [28] A highly stereoselective synthesis of 2,3,4,5-tetrasubstituted-trans-2,3-dihydrofurans
    Cao, WG
    Ding, WY
    Chen, J
    Chen, YL
    Zang, Q
    Chen, GD
    SYNTHETIC COMMUNICATIONS, 2004, 34 (09) : 1599 - 1608
  • [29] Synthesis of 1,3,4,5-tetrasubstituted pyrazoles from substituted hydrazines and β-ketoesters
    Bakanas, Ian
    Moura-Letts, Gustavo
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [30] Electrochemical synthesis of 1,2,4,5-tetrasubstituted imidazoles from enamines and benzylamines
    Wang, Wenxing
    Zhang, Shuo
    Shi, Guang
    Chen, Zhiwei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (30) : 6682 - 6686