Strontium-catalyzed highly enantioselective Michael additions of malonates to enones

被引:92
作者
Agostinho, Magno
Kobayashi, Shu [1 ]
机构
[1] Univ Tokyo, Sch Chem, Dept Chem,HFRE Div, ERATO,JST,Bunkyo Ku, Tokyo 1130033, Japan
关键词
D O I
10.1021/ja710332h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel catalyst system based on a chiral strontium complex which promotes the catalytic asymmetric Michael addition reactions of malonates to enones has been developed. The conjugate addition reactions proceeded smoothly in the presence of 5 mol % of the chiral strontium catalyst, at room temperature, to afford the desired adducts in high yields and excellent enantioselectivities. This method provides an. efficient approach to the preparation of building blocks possessing various functional groups and possible sites for further functionalization.
引用
收藏
页码:2430 / 2431
页数:2
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共 39 条
  • [1] Organocatalytic asymmetric conjugate additions
    Almasi, Diana
    Alonso, Diego A.
    Najera, Carmen
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (03) : 299 - 365
  • [2] Catalysis of the Michael addition reaction by late transition metal complexes of BINOL-derived salens
    Annamalai, V
    DiMauro, EF
    Carroll, PJ
    Kozlowski, MC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) : 1973 - 1981
  • [3] [Anonymous], COMPREHENSIVE ASYMME
  • [4] Synthesis and characterization of monomeric Ba and Sr complexes with malonate and Lewis base ligands
    Bae, BJ
    Park, JT
    Suh, IH
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 648 (1-2) : 214 - 219
  • [5] Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
  • [6] Influence of support composition on the structure and reactivity of strontium base catalysts
    Bordawekar, SV
    Doskocil, EJ
    Davis, RJ
    [J]. CATALYSIS LETTERS, 1997, 44 (3-4) : 193 - 199
  • [7] Preparation and application of chiral spiro nitrogen-containing ligands for cobalt-catalyzed asymmetric Michael addition
    Chen, Chao
    Zhu, Shou-Fei
    Wu, Xin-Yan
    Zhou, Qi-Lin
    [J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (19) : 2761 - 2767
  • [8] Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions
    Christoffers, J
    Baro, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) : 1688 - 1690
  • [9] Influence of ionic liquids on the phase transfer-catalysed enantioselective Michael reaction
    Dere, RT
    Pal, RR
    Patil, PS
    Salunkhe, MM
    [J]. TETRAHEDRON LETTERS, 2003, 44 (28) : 5351 - 5353
  • [10] REMARKABLE CATALYSIS BY STRONTIUM ION IN S(N)2 AND E2 REACTIONS OCCURRING IN PROXIMITY TO A CROWN-ETHER STRUCTURE
    DODDI, G
    ERCOLANI, G
    LAPEGNA, P
    MENCARELLI, P
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (10) : 1239 - 1240