Diels-Alder reactions in water

被引:198
作者
Otto, S [1 ]
Engberts, JBFN [1 ]
机构
[1] Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands
关键词
D O I
10.1351/pac200072071365
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This review illustrates how water, as an environmentally friendly solvent, can have significant additional benefits when it is used as a solvent for the Diels-Alder reaction. The mechanism by which the unique properties of water enhance the rate and selectivity are discussed. Also, possibilities for the achievement of further increases in rate and enantioselectivity of aqueous Diels-Alder reactions through Lewis-acid and micellar catalysis are reviewed.
引用
收藏
页码:1365 / 1372
页数:8
相关论文
共 72 条
  • [1] REGIOCHEMICAL AND STEREOCHEMICAL VARIATIONS IN DIELS-ALDER REACTIONS
    ARSENIYADIS, S
    RODRIGUEZ, R
    YASHUNSKY, DV
    CAMARA, J
    OURISSON, G
    [J]. TETRAHEDRON LETTERS, 1994, 35 (27) : 4843 - 4846
  • [2] ACTIVATION AND REACTION VOLUMES IN SOLUTION
    ASANO, T
    LENOBLE, J
    [J]. CHEMICAL REVIEWS, 1978, 78 (04) : 407 - 489
  • [3] ASSFELD M, 1995, J CHEM SOC CHEM COMM, P1371
  • [4] CORRELATION OF SOLVENT EFFECTS ON STEREOSELECTIVITIES OF DIELS-ALDER REACTIONS BY MEANS OF LINEAR FREE ENERGY RELATIONSHIPS - A NEW EMPIRICAL MEASURE OF SOLVENT POLARITY
    BERSON, JA
    MUELLER, WA
    HAMLET, Z
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (02) : 297 - &
  • [5] SOLVENT EFFECTS ON A DIELS-ALDER REACTION FROM COMPUTER-SIMULATIONS
    BLAKE, JF
    JORGENSEN, WL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) : 7430 - 7432
  • [6] DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTIONS - ENFORCED HYDROPHOBIC INTERACTIONS BETWEEN DIENE AND DIENOPHILE
    BLOKZIJL, W
    BLANDAMER, MJ
    ENGBERTS, JBFN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) : 4241 - 4246
  • [7] BLOKZIJL W, 1991, THESIS U GRONINGEN
  • [8] SELECTIVE DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTIONS AND SUSPENSIONS
    BRESLOW, R
    MAITRA, U
    RIDEOUT, D
    [J]. TETRAHEDRON LETTERS, 1983, 24 (18) : 1901 - 1904
  • [9] SOLVENT EFFECTS ON ENDO/EXO-SELECTIVITIES AND REGIO-SELECTIVITIES OF DIELS-ALDER REACTIONS OF CARBONYL-CONTAINING DIENOPHILES
    CATIVIELA, C
    GARCIA, JI
    MAYORAL, JA
    SALVATELLA, L
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (04): : 847 - 851
  • [10] Solvent effects on Diels-Alder reactions. The use of aqueous mixtures of fluorinated alcohols and the study of reactions of acrylonitrile
    Cativiela, C
    Garcia, JI
    Gil, J
    Martinez, RM
    Mayoral, JA
    Salvatella, L
    Urieta, JS
    Mainar, AM
    Abraham, MH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (03): : 653 - 660