Axially chiral guanidine as enantioselective base catalyst for 1,4-addition reaction of 1,3-dicarbonyl compounds with conjugated nitroalkenes

被引:225
作者
Terada, M [1 ]
Ube, H [1 ]
Yaguchi, Y [1 ]
机构
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
关键词
D O I
10.1021/ja057848d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new strategy for designing chiral guanidine molecules is presented, which features the introduction of an axially chiral binaphthyl backbone. The axially chiral guanidine catalysts thus developed facilitated the highly enantioselective 1,4-addition reaction of 1,3-dicarbonyl compounds with a broad range of conjugated nitroalkenes and showed extremely high catalytic activity. Copyright © 2006 American Chemical Society.
引用
收藏
页码:1454 / 1455
页数:2
相关论文
共 34 条
  • [1] Synthesis and applications of C2-symmetric guanidine bases
    Allingham, MT
    Howard-Jones, A
    Murphy, PJ
    Thomas, DA
    Caulkett, PWR
    [J]. TETRAHEDRON LETTERS, 2003, 44 (48) : 8677 - 8680
  • [2] Development of a catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes for the synthesis of endothelin-A antagonist ABT-546. Scope, mechanism, and further application to the synthesis of the antidepressant rolipram
    Barnes, DM
    Ji, JG
    Fickes, MG
    Fitzgerald, MA
    King, SA
    Morton, HE
    Plagge, FA
    Preskill, M
    Wagaw, SH
    Wittenberger, SJ
    Zhang, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) : 13097 - 13105
  • [3] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
  • [4] ENANTIOMERICALLY PURE GUANIDINE-CATALYZED ASYMMETRIC NITROALDOL REACTION
    CHINCHILLA, R
    NAJERA, C
    SANCHEZAGULLO, P
    [J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (07) : 1393 - 1402
  • [5] The synthesis of C2-symmetric and axially chiral compounds for recognition and catalysis
    Clews, J
    Curtis, ADM
    Malkin, H
    [J]. TETRAHEDRON, 2000, 56 (44) : 8735 - 8746
  • [6] Enantioselective synthesis of α-amino nitriles from N-benzhydryl imines and HCN with a chiral bicyclic guanidine as catalyst
    Corey, EJ
    Grogan, MJ
    [J]. ORGANIC LETTERS, 1999, 1 (01) : 157 - 160
  • [7] In the golden age of organocatalysis
    Dalko, PI
    Moisan, L
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175
  • [8] Ni(II)-bis[(R,R)-N,N′-dibenzylcyclohexane-1,2-diamine]Br2 catalyzed enantioselective Michael additions of 1,3-dicarbonyl compounds to conjugated nitroalkenes
    Evans, DA
    Seidel, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) : 9958 - 9959
  • [9] Hannon C. L., 1993, Bioorg. Chem. Front, V3, P193
  • [10] Recent progress in the asymmetric organocatalysis
    Hayashi, Y
    [J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2005, 63 (05) : 464 - 477