Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones using MgBr2 as promoter via a one-pot three-component reaction

被引:23
作者
Wei, HX [1 ]
Jasoni, RL [1 ]
Hu, JL [1 ]
Li, GG [1 ]
Paré, PW [1 ]
机构
[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA
关键词
Baylis-Hillman adducts; magnesium bromine; alpha; beta-acetylenic ketones; (Z)-beta-bromovinyl ketone;
D O I
10.1016/j.tet.2004.08.097
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first time steroselective synthesis of (Z)-beta-bromo Baylis-Hillman ketones has been achieved using a one-pot three-component reaction. The new system uses MgBr2 as both the Lewis acidic promoter and the bromine source for the Michael-type addition with alpha,beta-acetylenic ketones to form an active beta-bromo allenolate intermediate, which in turn attacks various aldehydes to afford beta-bromo Baylis-Hillman adducts in good yields and Z-selectivity. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:10233 / 10237
页数:5
相关论文
共 22 条
  • [11] Shi M, 2002, HELV CHIM ACTA, V85, P841, DOI 10.1002/1522-2675(200203)85:3<841::AID-HLCA841>3.0.CO
  • [12] 2-U
  • [13] BETA-HALOVINYL KETONES - SYNTHESIS FROM ACETYLENIC KETONES
    TANIGUCHI, M
    KOBAYASHI, S
    NAKAGAWA, M
    HINO, T
    KISHI, Y
    [J]. TETRAHEDRON LETTERS, 1986, 27 (39) : 4763 - 4766
  • [14] ALDOL REACTION OF ALLENOLATES GENERATED VIA 1,4-ADDITION OF IODIDE ANION OR ITS EQUIVALENT TO ALPHA, BETA-ACETYLENIC KETONES
    TANIGUCHI, M
    HINO, T
    KISHI, Y
    [J]. TETRAHEDRON LETTERS, 1986, 27 (39) : 4767 - 4770
  • [15] A ruthenium-catalyzed three-component coupling to form E-vinyl chlorides
    Trost, BM
    Pinkerton, AB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) : 1988 - 1989
  • [16] Trost BM, 2000, ANGEW CHEM INT EDIT, V39, P360, DOI 10.1002/(SICI)1521-3773(20000117)39:2<360::AID-ANIE360>3.0.CO
  • [17] 2-9
  • [18] Stereoselective aldol coupling of α,β-acetylenic ketones promoted by MgI2
    Wei, HX
    Hu, JL
    Purkiss, DW
    Paré, PW
    [J]. TETRAHEDRON LETTERS, 2003, 44 (05) : 949 - 952
  • [19] Synthesis of β-iodo-α-(hydroxyalkyl)acrylates:: a convenient and stereoselective reaction
    Wei, HX
    Gao, JJ
    Li, GG
    Paré, PW
    [J]. TETRAHEDRON LETTERS, 2002, 43 (32) : 5677 - 5680
  • [20] Substoichiometric TiCl4-mediated vicinal difunctionalization of α,β-acetylenic ketones for the synthesis of β-halo Baylis-Hillman olefins
    Wei, HX
    Gao, JJ
    Li, GG
    [J]. TETRAHEDRON LETTERS, 2001, 42 (52) : 9119 - 9122