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
  • [1] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction
    Basavaiah, D
    Rao, PD
    Hyma, RS
    [J]. TETRAHEDRON, 1996, 52 (24) : 8001 - 8062
  • [2] Ciganek E., 1997, ORG REACTIONS, V51, P201
  • [3] The aldol reaction of allenolates with aldehydes in the presence of magnesium diiodide (MgI2) as catalyst
    Deng, GH
    Hu, H
    Wei, HX
    Paré, PW
    [J]. HELVETICA CHIMICA ACTA, 2003, 86 (10) : 3510 - 3515
  • [4] Highly stereospecific, cross-coupling reactions of alkenylsilacyclobutanes
    Denmark, SE
    Choi, JY
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) : 5821 - 5822
  • [5] Kataoka T, 2000, ANGEW CHEM INT EDIT, V39, P2358, DOI 10.1002/1521-3773(20000703)39:13<2358::AID-ANIE2358>3.0.CO
  • [6] 2-Y
  • [7] Lee V. J., 1991, COMPREHENSIVE ORGANI, V4, P139
  • [8] Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones via a one-pot three-component X-C/C-C formation reaction
    Li, GG
    Wei, HX
    Gao, JJ
    Johnson, J
    [J]. SYNTHETIC COMMUNICATIONS, 2002, 32 (11) : 1765 - 1773
  • [9] The asymmetric catalytic aldol reaction of allenolates with aldehydes using N-fluoroacyl oxazaborolidine as the catalyst
    Li, GG
    Wei, HX
    Phelps, BS
    Purkiss, DW
    Kim, SH
    [J]. ORGANIC LETTERS, 2001, 3 (06) : 823 - 826
  • [10] Titanium(IV) bromide and boron(III) tribromide promoted reactions of arylaldehydes with 3-butyn-2-one, methyl propiolate and propynenitrile
    Shi, M
    Wang, CJ
    [J]. TETRAHEDRON, 2002, 58 (44) : 9063 - 9074