Götz Sven, Schneider Andreas, Lützen Arne
Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Str. 1, D-53121 Bonn, Germany.
Beilstein J Org Chem. 2019 Jun 18;15:1339-1346. doi: 10.3762/bjoc.15.133. eCollection 2019.
The preparative resolution of a trifunctionalized -symmetrical chiral cyclotriveratrylene derivative was achieved via high-performance liquid chromatography (HPLC) on a chiral stationary phase. This approach is a promising alternative to the previously reported resolution through formation of diastereomeric esters because it involves fewer synthetic steps and is less prone to thermal (re)racemization. During these studies an intermediate saddle conformer could also be isolated and characterized by H and C NMR spectroscopy. The HPLC separation method was further developed in order to allow investigations on the racemization behavior of the cyclotriveratrylene derivative.
通过在手性固定相上进行高效液相色谱（HPLC），实现了三官能化对称手性环三藜芦烃衍生物的制备拆分。这种方法是一种有前景的替代方法，可替代先前报道的通过形成非对映体酯进行拆分的方法，因为它涉及的合成步骤更少，且不太容易发生热（再）外消旋化。在这些研究中，还可以分离出一种中间鞍形构象体，并通过氢核磁共振（¹H NMR）和碳核磁共振（¹³C NMR）光谱对其进行表征。为了能够研究环三藜芦烃衍生物的外消旋化行为，进一步改进了HPLC分离方法。
