Asymmetric Synthesis of Complex Heterocycles from Simple Cyclopropanes

该项目致力于开发一系列形式[3，2]环加成反应的给体-受体环丙烷，作为简单但广泛有用的构件。用醛、酮、环亚胺、腈和偶氮化合物截留Lewis酸活化的丙二酰环丙烷，分别得到四氢呋喃、环烯醇醚、双环吡咯烷、吡咯烷和吡唑烷。该项目可能导致快速获得天然存在的生物活性化合物的关键亚结构，如枝叶二萜类化合物。有了这个奖项，有机和高分子化学计划将支持北卡罗来纳大学教堂山分校化学系的杰弗里·约翰逊教授的研究。约翰逊教授的研究主要集中在化学合成领域。在这笔赠款的支持下开发的化学预计将对实验室制备结构感兴趣的杂环结构的效率产生积极影响。这种亚结构普遍存在于生物活性天然产物和医药制剂中。

This project seeks to develop donor-acceptor cyclopropanes as simple, but broadly useful building blocks for a range of formal [3+2] cycloaddition reactions. Intercepting Lewis acid activated malonyl cyclopropanes with aldehydes, ketenes, cyclic imines, nitriles, and azo compounds will be studied to deliver tetrahydrofurans, cyclic enol ethers, bicyclic pyrrolidines, pyrrolines, and pyrazolidines, respectively. The project could lead to the rapid access to key substructures of naturally occurring biologically active compounds like the cladiellin diterpenes.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Jeffrey Johnson of the Department of Chemistry at the University of North Carolina at Chapel Hill. Professor Johnson's research efforts are broadly in the area of chemical synthesis. The chemistry to be developed under the aegis of this grant is projected to positively impact the efficiency with which structurally interesting heterocyclic structures may be prepared in the laboratory. Such substructures are ubiquitous in biologically active natural products and medicinal agents.