Synthesis, resolution, and absolute configuration of difunctionalized Troger's base derivatives

被引：42
|
作者：
Kiehne, Ulf [2 ]
Bruhn, Torsten [1 ]
Schnakenburg, Gregor [3 ]
Froehlich, Roland [4 ]
Bringmann, Gerhard [1 ]
Luetzen, Arne [2 ]
机构：
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[2] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
[3] Univ Bonn, Inst Anorgan Chem, D-53121 Bonn, Germany
[4] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 14期
关键词：
chiral resolution; circular dichroism; configuration determination; quantum chemical calculations; Troger's base;
D O I：
10.1002/chem.200701960
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Two racemic derivatives of Troger's base, the 2,8-diboronic acid ester 6 and the 3,9-dibromo-substituted derivative 5, were synthesized and successfully resolved by HPLC on a chiral stationary Whelk-01 phase on a semipreparative scale, thereby giving rise to both enantiomers in a pure form. These functionalized C-2- symmetric building blocks are valuable precursors for a variety of further applications. Their absolute configurations were determined by comparison of their quantum chemically calculated CD and UV/Vis spectra with the experimental ones and were independently confirmed by X-ray diffraction analysis.
引用
收藏
页码：4246 / 4255
页数：10
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