HIGHLY STEREOSELECTIVE DOUBLE MICHAEL CYCLIZATION OF 1-PHENYLSULFINYL AND SULFONYL ANALOGS OF THE NAZAROV REAGENT

被引:20
作者
SPINO, C [1 ]
DESLONGCHAMPS, P [1 ]
机构
[1] UNIV SHERBROOKE,FAC SCI,DEPT CHIM,SYNTHESE ORGAN LAB,SHERBROOKE J1K 2R1,QUEBEC,CANADA
关键词
D O I
10.1016/S0040-4039(00)94474-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The base-catalyzed double Michael addition of the β-keto sulfoxide 5 with 2-carbomethoxy-2-cyclohexenone (1) proceeds, after elimination of the sulfoxide moiety during chromatography on silica, to give the dehydrodecalin adduct 6 with high stereoselectivity. © 1990.
引用
收藏
页码:3969 / 3972
页数:4
相关论文
共 10 条
  • [1] CAINE D, 1976, ORG REACTIONS, V23, P1
  • [2] DESLONGCHAMPS P, 1988, TETRAHEDRON LETT, V29, P5117
  • [3] GOLDMANN S, 1980, SYNTHESIS-STUTTGART, P640
  • [4] USE OF BETA-KETO SULFONES AS SYNTHETIC INTERMEDIATES
    HOUSE, HO
    LARSON, JK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) : 61 - &
  • [5] LAVALLEE JF, UNPUB CAN J CHEM
  • [6] LAVALLEE JF, 1988, THESIS U SHERBROOKE
  • [7] Lee R. A., 1973, TETRAHEDRON LETT, V14, P3333
  • [8] A SIMPLE METHOD FOR THE EFFICIENT SYNTHESIS OF UNSATURATED BETA-DICARBONYL COMPOUNDS
    LIOTTA, D
    BARNUM, C
    PULEO, R
    ZIMA, G
    BAYER, C
    KEZAR, HS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (14) : 2920 - 2923
  • [9] DIELS-ALDER REACTIONS OF 2-CARBOMETHOXY-2-CYCLOHEXEN-1-ONE
    LIU, HJ
    NGOOI, TK
    BROWNE, ENC
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (12): : 3143 - 3152
  • [10] RUEL R, TETRAHEDRON LETT