A novel hydrazide type organocatalyst for enantioselective Diels-Alder reactions

被引:7
作者
Suzuki, Ichiro
Ando, Masafumi
Shimabara, Rumiko
Hirata, Ai
Takeda, Kei
机构
[1] Minami-ku, Hiroshima 734-8553
关键词
DIARYLPROLINOL SILYL ETHER; CATALYSIS; DESIGN; SALTS;
D O I
10.1039/c0ob01138j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of a new class of hydrazide type organocatalyst, (4R, 5R)-1,3-bis(isopropylamino)4,5- dihenylimidazolidin-2-one 2a, for enantioselective Diels-Alder reactions between cyclopentadiene and alpha,beta-unsaturated aldehydes are presented. The new organocatalyst 2a promoted the reaction, affording Diels-Alder adducts in good yields with good levels of enantioselectivity.
引用
收藏
页码:3033 / 3040
页数:8
相关论文
共 42 条
  • [1] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction
    Ahrendt, KA
    Borths, CJ
    MacMillan, DWC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) : 4243 - 4244
  • [2] DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR
    BECKE, AD
    [J]. PHYSICAL REVIEW A, 1988, 38 (06): : 3098 - 3100
  • [3] Aziridin-2-yl methanols as organocatalysts in Diels-Alder reactions and Friedel-Crafts alkylations of N-methyl-pyrrole and N-methyl-indole
    Bonini, Bianca F.
    Capito, Elena
    Comes-Franchini, Mauro
    Fochi, Mariafrancesca
    Riccia, Alfredo
    Zwanenburg, Binne
    [J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (22) : 3135 - 3143
  • [4] The α-effect in cyclic secondary amines: new scaffolds for iminium ion accelerated transformations
    Brazier, John B.
    Cavill, Julie L.
    Elliott, Richard L.
    Evans, Gareth
    Gibbs, Timothy J. K.
    Jones, Ian L.
    Platts, James A.
    Tomkinson, Nicholas C. O.
    [J]. TETRAHEDRON, 2009, 65 (48) : 9961 - 9966
  • [5] The α-effect in iminium ion catalysis
    Cavill, JL
    Elliott, RL
    Evans, G
    Jones, IL
    Platts, JA
    Ruda, AM
    Tomkinson, NCO
    [J]. TETRAHEDRON, 2006, 62 (2-3) : 410 - 421
  • [6] Iminium ion catalysis:: Use of the α-effect in the acceleration of the Diels-Alder reaction
    Cavill, JL
    Peters, JU
    Tomkinson, NCO
    [J]. CHEMICAL COMMUNICATIONS, 2003, (06) : 728 - 729
  • [7] Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO
  • [8] 2-B
  • [9] Phase transfer Wittig reaction with 1,3-dioxolan-2-yl-methyltriphenyl phosphonium salts: an efficient method for vinylogation of aromatic aldehydes
    Daubresse, N
    Francesch, C
    Rolando, C
    [J]. TETRAHEDRON, 1998, 54 (36) : 10761 - 10770
  • [10] Asymmetric organocatalysis: From infancy to adolescence
    Dondoni, Alessandro
    Massi, Alessandro
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) : 4638 - 4660