Zhan Desheng, Yang Gang, Zhou Tieli, Nallapati Sashirekha, Zhang Xiaofeng
College of Chemistry, Changchun Normal University, Changchun 130032, China.
College of Food Science and Engineering, Changchun University, Changchun 130022, China.
Molecules. 2025 Apr 2;30(7):1594. doi: 10.3390/molecules30071594.
A concerted five-component reaction strategy has been developed, featuring double [3+2] cycloadditions utilizing aspartic acid. This approach provides valuable insights into mechanistic pathways, allowing for the distinction between concerted and stepwise processes based on reaction efficiency and diastereoselectivity. Both aspartic and glutamic acids have been employed for a thorough evaluation and exploration of decarboxylation-driven double annulations. This method effectively constructs pyrrolizidine frameworks through a concerted double 1,3-dipolar cycloaddition with aspartic acid, as well as tetrahydropyrrolizinones via three-component double annulations, which include decarboxylative 1,3-dipolar cycloaddition and lactamization with glutamic acid. These highly convergent, decarboxylation-driven multicomponent reactions (MCRs) efficiently produce fused polyheterocyclic systems while being environmentally friendly, generating only CO and water as byproducts.
一种协同的五组分反应策略已经被开发出来，其特点是利用天冬氨酸进行双[3+2]环加成反应。这种方法为反应机理途径提供了有价值的见解，能够根据反应效率和非对映选择性区分协同过程和分步过程。天冬氨酸和谷氨酸都已被用于对脱羧驱动的双环化反应进行全面评估和探索。该方法通过与天冬氨酸进行协同双1,3-偶极环加成反应有效地构建了吡咯里西啶骨架，以及通过包括脱羧1,3-偶极环加成反应和与谷氨酸进行内酰胺化反应的三组分双环化反应构建了四氢吡咯里嗪酮。这些高度汇聚的、脱羧驱动的多组分反应（MCRs）能够高效地生成稠合多杂环体系，同时对环境友好，仅产生一氧化碳和水作为副产物。
