Departamento de Química, Facultad de Ciencias, Universidad de Burgos, 09001, Burgos, Spain.
J Org Chem. 2022 Jul 15;87(14):9391-9398. doi: 10.1021/acs.joc.2c00694. Epub 2022 Jun 27.
The diastereoselective synthesis of two families of pyrrolopiperazine-2,6-diones is presented. These compounds were prepared by one-pot Ugi/nucleophilic substitution/N-acylation/debenzoylation/(elimination) sequences. This novel route provides straightforward access to a wide variety of pyrrolopiperazine-2,6-diones with high chemical yields and complete diastereoselectivities. The proposed synthetic strategy poses a significant improvement compared to the syntheses of pyrrolopiperazine-2,6-diones previously described, as it allows introduction of different substituents to the C4 position and the diastereoselective generation of a new stereogenic center on the bridgehead carbon (C8a).
呈现了两类吡咯哌嗪-2,6-二酮的非对映选择性合成。这些化合物通过一锅 Ugi/亲核取代/N-酰化/脱苯甲酰基/（消除）序列制备。这种新方法提供了直接获得具有高化学产率和完全非对映选择性的各种吡咯哌嗪-2,6-二酮的途径。与之前描述的吡咯哌嗪-2,6-二酮的合成相比，所提出的合成策略有了显著的改进，因为它允许在 C4 位置引入不同的取代基，并在手性中心桥碳原子（C8a）上非对映选择性地生成新的立体中心。
