Electron deficiency of aldehydes controls the pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes and ketones in water

被引:57
作者
Chimni, SS [1 ]
Mahajan, D [1 ]
机构
[1] Guru Nanak Dev Univ, Dept Chem, Amritsar 143005, Punjab, India
关键词
pyrrolidine catalysis; heterocyclic aldol; cross-aldol; aqueous medium; beta-hydroxy ketones;
D O I
10.1016/j.tet.2005.03.045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthetically useful pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes with ketones in water affords the aldol addition product in up to 93% yield. Electrophilicity of the aldehydes controls the course of the reaction. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5019 / 5025
页数:7
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共 50 条
  • [1] AGAMI C, 1987, B SOC CHIM FR, P358
  • [2] ALVAREZIBARRA C, 1992, J CHEM RES S, V326, P2674
  • [3] MECHANISTIC INSIGHTS FROM AB-INITIO CALCULATIONS ON A NITROGEN ANALOG OF THE BORON MEDIATED ALDOL REACTION
    BERNARDI, A
    GENNARI, C
    GOODMAN, JM
    LEUE, V
    PATERSON, I
    [J]. TETRAHEDRON, 1995, 51 (16) : 4853 - 4866
  • [4] Direct catalytic asymmetric aldol reactions of aldehydes
    Bogevig, A
    Kumaragurubaran, N
    Jorgensen, KA
    [J]. CHEMICAL COMMUNICATIONS, 2002, (06) : 620 - 621
  • [5] 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
  • [6] Direct organocatalytic aldol reactions in buffered aqueous media
    Córdova, A
    Notz, W
    Barbas, CF
    [J]. CHEMICAL COMMUNICATIONS, 2002, (24) : 3024 - 3025
  • [7] Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde
    Córdova, A
    Notz, W
    Barbas, CF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) : 301 - 303
  • [8] Mineral catalysis of a potentially prebiotic aldol condensation
    De Graaf, RM
    Visscher, J
    Xu, Y
    Arrhenius, G
    Schwartz, AW
    [J]. JOURNAL OF MOLECULAR EVOLUTION, 1998, 47 (05) : 501 - 507
  • [9] REACTIONS IN THE FORMOL BIOID - THE ORIGIN OF THE BRANCHED CHAINS OF ISOPRENOIDS, VALINE, AND LEUCINES
    DECKER, P
    SCHWEER, H
    [J]. ORIGINS OF LIFE AND EVOLUTION OF THE BIOSPHERE, 1984, 14 (1-4): : 335 - 342
  • [10] Aqueous aldol catalysis by a nicotine metabolite
    Dickerson, TJ
    Janda, KD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (13) : 3220 - 3221