Heterocyclic Chemistry of Bicyclo[1.1.0]butanes

双环[1.1.0]丁烷的杂环化学

• 批准号: 0910560
• 负责人: Peter Wipf
• 金额: $ 39万
• 依托单位: University of Pittsburgh
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2009
• 资助国家: 美国
• 起止时间: 2009-08-15 至 2014-07-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=0910560&HistoricalAwards=false
• 关键词: Heterocyclic; Chemistry; Bicyclo; 1.1.0; butanes

This project will focus on the exploratory chemistry of a strained organic ring system, the bicyclobutane group. Steric strain has always been one of the major driving forces for C-C and C-heteroatom bond formations, but in contrast to cyclopropanes, oxiranes, and aziridines, only minimal progress has been made in the past in the application of the bicyclo[1.1.0]butane building block in organic synthesis. Fundamentally, bicyclobutanes represent 4-carbon alkyne surrogates. Studies to harness their intramolecular pericyclic processes will take advantage of the attachment of suitable alkenes and alkynes to a nitrogen tether and provide access to novel polycyclic pyrrolidines. Additionally, hypothesis driven transition metal catalyzed transformations will be carried out to identify new reactions and construct useful new heterocyclic scaffolds.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Peter Wipf of the Department of Chemistry at the University of Pittsburgh. Professor Wipf's research efforts revolve around the total synthesis of natural products, organometallic and heterocyclic processes, and combinatorial, medicinal and computational chemistry. The study of chemical reactivity and the use of synthesis to augment the chemical toolbox assists the development of new therapeutic strategies. The discovery of fundamentally new reaction pathways in his laboratory is stimulated by exploratory studies of transition metal complexes. Successful development of the methodology will have an impact on discovery and process chemistry in the pharmaceutical, agricultural and fine chemical industries.

这个项目将集中在一种应变的有机环系--双环丁烷基团的探索化学上。空间菌株一直是C-C和C-杂原子键形成的主要驱动力之一，但与环丙烷、环氧乙烷和氮杂环丙烷相比，双环[1.1.0]丁烷在有机合成中的应用过去只取得了很小的进展。从根本上说，双环丁烷代表4-碳炔类替代品。利用其分子内周环过程的研究将利用合适的烯烃和炔烃与氮链的连接，并提供获得新型多环吡咯烷的途径。此外，还将进行假说驱动的过渡金属催化转化，以确定新的反应并构建有用的新杂环支架。有了这个奖项，有机和高分子化学计划将支持匹兹堡大学化学系的Peter Wipf教授的研究。Wipf教授的研究工作围绕天然产物、有机金属和杂环过程以及组合、药物和计算化学的全合成展开。对化学反应的研究和使用合成来增强化学工具箱有助于开发新的治疗策略。在他的实验室里，过渡金属络合物的探索性研究刺激了从根本上新的反应路径的发现。该方法的成功开发将对制药、农业和精细化工行业的发现和过程化学产生影响。