The nucleophilic 5-endo-trig cyclization of gem-difluoroolefins with homoallylic functional groups:: syntheses of ring-fluorinated dihydroheteroaromatics

被引:50
作者
Ichikawa, J [1 ]
Fujiwara, M
Wada, Y
Okauchi, T
Minami, T
机构
[1] Kyushu Inst Technol, Dept Appl Chem, Kitakyushu, Fukuoka 8048550, Japan
[2] Univ Tokyo, Grad Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan
关键词
D O I
10.1039/b004978f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
gem-Difluoroolefins bearing homoallylic tosylamido, hydroxy, or mercapto groups undergo intramolecular nucleophilic substitution of the nitrogen, oxygen, or sulfur with loss of fluorine via a 5-endo-trig process, leading to 2-fluoro-2-pyrrolines, 5-fluoro-2,3-dihydrofurans, or -thiophenes in high yields.
引用
收藏
页码:1887 / 1888
页数:2
相关论文
共 37 条
  • [1] Reaction of thioglycolate with alpha-fluoro-beta-(phenylthio)enones (or -enals): Synthesis of substituted alpha-carboxy-gamma-fluorothiophenes
    Andres, DF
    Laurent, EG
    Marquet, BS
    [J]. TETRAHEDRON LETTERS, 1997, 38 (06) : 1049 - 1052
  • [2] 5-ENDO-TRIGONAL REACTIONS - DISFAVORED RING-CLOSURE
    BALDWIN, JE
    CUTTING, J
    DUPONT, W
    KRUSE, L
    SILBERMAN, L
    THOMAS, RC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) : 736 - 738
  • [3] RULES FOR RING-CLOSURE - RING FORMATION BY CONJUGATE ADDITION OF OXYGEN NUCLEOPHILES
    BALDWIN, JE
    THOMAS, RC
    KRUSE, LI
    SILBERMAN, L
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (24) : 3846 - 3852
  • [4] RULES FOR RING-CLOSURE
    BALDWIN, JE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) : 734 - 736
  • [5] Banks R.E., 1994, ORGANOFLUORINE CHEM
  • [6] Model studies of the overall 5-endo-trig iodocyclization of homoallylic alcohols
    Bedford, SB
    Bell, KE
    Bennett, F
    Hayes, CJ
    Knight, DW
    Shaw, DE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (15): : 2143 - 2153
  • [7] 5-endo-trig radical cyclizations of bromomethyldimethylsilyl diisopropylpropargylic ethers.: A highly diastereoselective access to functionalized cyclopentanes
    Bogen, S
    Gulea, M
    Fensterbank, L
    Malacria, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) : 4920 - 4925
  • [8] Synthesis of erythro and threo furanoid glycals using 5-endo-trig selenoetherification as key step
    Bravo, F
    Kassou, M
    Castillón, S
    [J]. TETRAHEDRON LETTERS, 1999, 40 (06) : 1187 - 1190
  • [9] SYNTHESIS OF 3-TRIFLUOROMETHYLFURANS FROM BETA,BETA-BIS(TRIFLUOROMETHYL) ALPHA,BETA-UNSATURATED KETONES AND TIN(II) CHLORIDE
    BURGER, K
    HELMREICH, B
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (04) : 348 - 349
  • [10] Cassayre J, 1999, SYNLETT, P501