A homo-proline tetrazole as an improved organocatalyst for the asymmetric Michael addition of carbonyl compounds to nitro-olefins

被引:136
作者
Mitchell, CET [1 ]
Cobb, AJA [1 ]
Ley, SV [1 ]
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
关键词
asymmetric; nitro-Michael; organocatalysis; homoproline; tetrazole;
D O I
10.1055/s-2005-862392
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new homo-proline tetrazole derivative 7 has been prepared and shown to have improved properties for achieving asymmetric Michael addition of carbonyl compounds to nitro-olefins.
引用
收藏
页码:611 / 614
页数:4
相关论文
共 42 条
  • [21] Hajos Z. G., 1971, [No title captured], Patent No. 2102623
  • [22] ASYMMETRIC SYNTHESIS OF BICYCLIC INTERMEDIATES OF NATURAL PRODUCT CHEMISTRY
    HAJOS, ZG
    PARRISH, DR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) : 1615 - 1621
  • [23] Rational design of asymmetric organocatalysts - increased reactivity and solvent scope with a tetrazolic acid
    Hartikka, A
    Arvidsson, PI
    [J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (12) : 1831 - 1834
  • [24] The direct and enantioselective, one-pot, three-component, cross-Mannich reaction of aldehydes
    Hayashi, Y
    Tsuboi, W
    Ashimine, I
    Urushima, T
    Shoji, M
    Sakai, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) : 3677 - 3680
  • [25] A new class of chiral pyrrolidine-pyridine conjugate base catalysts for use in asymmetric Michael addition reactions
    Ishii, T
    Fujioka, S
    Sekiguchi, Y
    Kotsuki, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) : 9558 - 9559
  • [26] Direct L-proline-catalyzed asymmetric α-amination of ketones
    Kumaragurubaran, N
    Juhl, K
    Zhuang, W
    Bogevig, A
    Jorgensen, KA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (22) : 6254 - 6255
  • [27] New mechanistic studies on the proline-catalyzed aldol reaction
    List, B
    Hoang, L
    Martin, HJ
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (16) : 5839 - 5842
  • [28] Proline-catalyzed asymmetric reactions
    List, B
    [J]. TETRAHEDRON, 2002, 58 (28) : 5573 - 5590
  • [29] Efficient proline-catalyzed Michael additions of unmodified ketones to nitro olefins
    List, B
    Pojarliev, P
    Martin, HJ
    [J]. ORGANIC LETTERS, 2001, 3 (16) : 2423 - 2425
  • [30] Proline-catalyzed asymmetric aldol reactions between ketones and α-unsubstituted aldehydes
    List, B
    Pojarliev, P
    Castello, C
    [J]. ORGANIC LETTERS, 2001, 3 (04) : 573 - 575