Diastereoselectivity controlled by electrostatic repulsion between the negative charge on a trifluoromethyl group and that on aromatic rings

被引:46
作者
Katagiri, T [1 ]
Yamaji, S [1 ]
Handa, M [1 ]
Irie, M [1 ]
Uneyama, K [1 ]
机构
[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan
关键词
D O I
10.1039/b105602f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Intramolecular electrostatic repulsions between the local negative charge on a trifluoromethyl group and that on the ortho position of an aryl moiety of a nucleophile was found to be a controlling factor of the diastereoselectivity in a cyclopropanation reaction, in which the electrostatic repulsion was evaluated quantitatively.
引用
收藏
页码:2054 / 2055
页数:2
相关论文
共 11 条
  • [1] VAN DER WAALS VOLUMES + RADII
    BONDI, A
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) : 441 - +
  • [2] Aromatic interactions
    Hunter, CA
    Lawson, KR
    Perkins, J
    Urch, CJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (05): : 651 - 669
  • [3] ISRAELACHIVILI N, 1985, INTERMOLECULAR SURFA
  • [4] Intramolecular SN2 reaction α- to a trifluoromethyl group:: preparation of 1-cyano-2-trifluoromethylcyclopropane
    Katagiri, T
    Irie, M
    Uneyama, K
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (13) : 2583 - 2589
  • [5] A chemistry of 2,3-epoxy-1,1,1-trifluoropropane
    Katagiri, T
    Uneyama, K
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2000, 105 (02) : 285 - 293
  • [6] Syntheses of optically active trifluoronorcoronamic acids
    Katagiri, T
    Irie, M
    Uneyama, K
    [J]. ORGANIC LETTERS, 2000, 2 (16) : 2423 - 2425
  • [7] Katagiri T, 1999, ENANTIOCONTROLLED SY, P161
  • [8] NAGAI T, 1992, J FLUORINE CHEM, V57, P29
  • [9] PURVIS GD, 1991, J COMPUT AID MOL DES, V5, P55
  • [10] About the ''physiological size'' of fluorine substituents: Comparison of sensorially active compounds with fluorine and methyl substituted analogues
    Schlosser, M
    Michel, D
    [J]. TETRAHEDRON, 1996, 52 (01) : 99 - 108