title: Synthesis, chiral resolution, and absolute configuration of dissymmetric 4,15-difunctionalized [2.2]paracyclophanes.
abstract: 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.
authors: Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn , Gerhard-Domagk-Str. 1, D-53121 Bonn, Germany.
authors: Georg
authors: G
authors: Meyer-Eppler
authors: Rebecca
authors: R
authors: Sure
authors: Andreas
authors: A
authors: Schneider
authors: Gregor
authors: G
authors: Schnakenburg
authors: Stefan
authors: S
authors: Grimme
authors: Arne
authors: A
authors: Lützen