Department of Drug Sciences, University of Pavia, via Taramelli 12, 27100 Pavia, Italy.
Centro Grandi Strumenti, University of Pavia, via Bassi 21, 27100 Pavia, Italy.
Molecules. 2020 Dec 19;25(24):6023. doi: 10.3390/molecules25246023.
During the past several years, the frequency of discovery of new molecular entities based on γ- or δ-lactam scaffolds has increased continuously. Most of them are characterized by the presence of at least one chiral center. Herein, we present the preparation, isolation and the absolute configuration assignment of enantiomeric 2-(4-bromophenyl)-1-isobutyl-6-oxopiperidin-3-carboxylic acid (-). For the preparation of racemic -, the Castagnoli-Cushman reaction was employed. (Semi)-preparative enantioselective HPLC allowed to obtain enantiomerically pure - whose absolute configuration was assigned by X-ray diffractometry. Compound (+)-()- represents a reference compound for the configurational study of structurally related lactams.
在过去的几年中，基于 γ-或 δ-内酰胺骨架的新分子实体的发现频率不断增加。它们大多数的特点是至少存在一个手性中心。在这里，我们介绍了对映体 2-(4-溴苯基）-1-异丁基-6-氧代哌啶-3-羧酸（-）的制备、分离和绝对构型分配。对于外消旋 - 的制备，采用了 Castagnoli-Cushman 反应。（半）制备性对映体选择性 HPLC 允许获得对映体纯的 -，其绝对构型通过 X 射线衍射法确定。化合物 (+)-()- 是对结构相关内酰胺进行构型研究的参考化合物。
