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

被引：43

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

页码：4246 / 4255

页数：10