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

来源：

CHEMICAL COMMUNICATIONS | 2001年 / 20期

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

页码：2054 / 2055

页数：2

共 13 条

[1] ELECTROSTATIC REPULSION BETWEEN MOLECULES OF LIKE CHARGE CAN BE MISINTERPRETED AS BINDING
STEMMER, P
KLEE, CB
FEBS LETTERS, 1990, 276 (1-2) : 71 - 74
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HSU, JP
KUO, YC
COLLOID AND POLYMER SCIENCE, 1995, 273 (09) : 881 - 885
[4] On the photophysics of molecules with charge-transfer excitations between aromatic rings
Ferretti, A
Lami, A
Villani, G
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[5] CORRELATION BETWEEN NEGATIVE CHARGE ON NITROGEN AND REACTIVITY OF AROMATIC NITRENES
REISER, A
LEYSHON, L
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (25) : 7487 - &
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FOWLER, PW
MOORE, GJ
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1988, 153 (03) : 1296 - 1300
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Motta, Claudio C.
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[9] An Update on Multiple Bonding between Heavier Main Group Elements: The Importance of Pauli Repulsion, Charge-Shift Character, and London Dispersion Force Effects
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[10] The negative electrostatic potential of the coordination between calcium and carboxyl/oxygen group in calcium-peptide complexes contributes to calcium utilization
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