1,2-Additions of silylenol ethers to 4-silyloxy-1-benzothiopyrylium triflates: A new and efficient method for the synthesis of 2-substituted benzothiopyran-4-ones

被引:0
作者
Beifuss, U
Tietze, M
Gehm, H
机构
关键词
1-benzothiopyrylium triflates; silylenol ether; 1,2-addition; 1,4-addition; S-heterocycles;
D O I
10.1055/s-1996-5339
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regioselective 1,2-addition of silylenol ethers to the C=S+-bond of 4-silyloxy-1-benzothiopyrylium triflates yields the corresponding bis-silylenol ethers which can be hydrolyzed selectively to give the respective ketosilylenol ethers or 1,5-diketones. The new method is an equivalent to the 1,4-addition of nucleophiles to beta-thio-alpha,beta-unsaturated cyclic ketones.
引用
收藏
页码:182 / 184
页数:3
相关论文
共 16 条
  • [1] BATTEN RJ, 1982, J CHEM SOC PERK T 1, P1177, DOI 10.1039/p19820001177
  • [2] BATTEN RJ, 1980, SYNTHESIS-STUTTGART, P910
  • [3] BROWNBRIDGE P, 1983, SYNTHESIS-STUTTGART, P85
  • [4] BROWNBRIDGE P, 1983, SYNTHESIS-STUTTGART, P1
  • [5] THE SYNTHESIS OF 2,3-DISUBSTITUTED CYCLOPENTENONES USING THE RAMBERG BACKLUND REACTION IN CONJUNCTION WITH ORGANOCOPPER CHEMISTRY
    CASY, G
    TAYLOR, RJK
    [J]. TETRAHEDRON, 1989, 45 (02) : 455 - 466
  • [6] THE PREPARATION OF THIATHROMBOXANE ANALOGS AND A FORMAL TOTAL SYNTHESIS OF DITHIATHROMBOXANE-A2 BASED ON CONJUGATE ADDITION-REACTIONS OF THIIN-4-ONES
    CASY, G
    LANE, S
    TAYLOR, RJK
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08): : 1397 - 1404
  • [7] Chapdelaine M. J., 1990, ORG REACTIONS, V38, P227
  • [8] SYNTHESIS OF 2-SUBSTITUTED CHROMONES, CHROMANONES, AND THEIR THIO ANALOGS USING ORGANOCOPPER REAGENTS
    CLARKE, PD
    FITTON, AO
    SUSCHITZKY, H
    WALLACE, TW
    DOWLATSHAHI, HA
    SUSCHITZKY, JL
    [J]. TETRAHEDRON LETTERS, 1986, 27 (01) : 91 - 94
  • [9] Colvin E. W., 1981, SILICON ORGANIC SYNT, P165
  • [10] A STEREOSELECTIVE SYNTHESIS OF ALPHA,BETA-UNSATURATED KETONES INVOLVING THE REACTIONS OF ORGANOCUPRATES WITH BETA-ALKYLTHIO ALPHA,BETA-ENONES
    DIETER, RK
    SILKS, LA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (24) : 4687 - 4701