对映体
绝对构型
化学
卤素
平面手性
平面的
分辨率(逻辑)
立体化学
组合化学
对映选择合成
有机化学
催化作用
计算机科学
计算机图形学(图像)
人工智能
烷基
作者
Georg Meyer‐Eppler,Rebecca Sure,Andreas Schneider,Gregor Schnakenburg,Stefan Grimme,Arne Lützen
摘要
Despite the fact that functionalized planar chiral [2.2]paracyclophanes have received a lot of attention, the chemistry of pseudo-meta 4,15-distubstituted [2.2]paracyclophanes is largely unexplored. This is mainly due to the fact that the 4,5-dibromo-functionalized [2.2]paracyclophane is much less prone to halogen-metal exchange reactions than its constitutional pseudo-ortho or pseudo-para isomers. Here, we give an account of an efficient protocol to achieve this, which allows the synthesis of a broad variety of 4,15-disubstituted [2.2]paracyclophanes. Furthermore, we were able to resolve several of the racemic compounds via chiral HPLC and assign the absolute configurations of the isolated enantiomers by X-ray diffraction and/or by the comparison of calculated and measured CD-spectra.
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