Asymmetric Synthesis of Complex Heterocycles from Simple Cyclopropanes

该项目旨在开发给体-受体环丙烷作为一系列形式[3+2]环加成反应的简单但广泛有用的结构单元。 研究了醛、烯酮、环亚胺、腈和偶氮化合物对刘易斯酸活化的丙二酰环丙烷的截留作用，分别得到四氢呋喃、环烯醇醚、双环吡咯烷、吡咯啉和吡唑烷。 该项目可能导致快速获得天然生物活性化合物的关键亚结构，如cladiellin二萜。有了这个奖项，有机和大分子化学计划正在支持查佩尔山的北卡罗来纳州大学化学系的杰弗里约翰逊教授的研究。 约翰逊教授的研究工作主要在化学合成领域。 在此资助下开发的化学预计将对实验室制备结构有趣的杂环结构的效率产生积极影响。 这样的亚结构普遍存在于生物活性天然产物和药剂中。

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.