Transition Metal-Catalyzed Novel Cycloadditions for Organic Synthesis

用于有机合成的过渡金属催化新型环加成反应

• 批准号: 1464754
• 负责人: WEIPING TANG
• 金额: $ 40.5万
• 依托单位: University of Wisconsin-Madison
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2015
• 资助国家: 美国
• 起止时间: 2015-08-01 至 2019-07-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1464754&HistoricalAwards=false
• 关键词: Transition; Metal; Catalyzed; Novel; Cycloadditions

With this award, the Chemical Synthesis Program in the Division of Chemistry is funding Professor Weiping Tang of the University of Wisconsin-Madison to develop novel transition metal-catalyzed cycloaddition reactions focused on generating valuable seven-membered rings. These new reactions have the potential to fill a significant knowledge gap in organic chemistry and lead to a fundamentally new body of research. Professor Tang is integrating his research into education plans through activities that increase the participation of underrepresented undergraduate and high school students. The broader impact of this work includes improved fundamental understanding on metal catalysis and cycloadditions, new chemical methods for the preparation of medicine and materials, and the training of students for careers in science. The project focuses on the development of rhodium-catalyzed [5+2]-cycloadditions of 3-acyloxy-1,4-enynes with alkynes, alkenes, allenes, and other pi-systems. Highly functionalized seven-membered rings are prepared from these readily available enynes. For example, various tropone-containing compounds can be efficiently synthesized using an alkyne as the 2-carbon component. With an alkene or allene as the 2-carbon component, multiple stereogenic centers are set within the seven-membered rings. Professor Tang is also investigating the mechanism and reactive intermediates involved in these novel [5+2]-cycloadditions. These new cycloaddition methods provide solutions for the longstanding challenge to develop efficient and stereoselective synthetic entries into mono- or polycyclic seven-membered rings.

有了这个奖项，化学系的化学合成项目资助威斯康星大学麦迪逊分校的Weiping Tang教授开发新型过渡金属催化的环加成反应，重点是生成有价值的七元环。这些新反应有可能填补有机化学中的一个重大知识空白，并导致一个全新的研究机构。唐教授正在通过增加代表性不足的本科生和高中生的参与活动，将他的研究纳入教育计划。这项工作的更广泛的影响包括提高对金属催化和环加成的基本理解，制备药物和材料的新化学方法，以及对学生进行科学职业培训。该项目的重点是发展铑催化的3-酰氧基-1，4-烯炔与炔、烯、联烯和其他π-体系的[5+2]-环加成反应。高度官能化的七元环由这些容易获得的烯炔制备。例如，使用炔作为2-碳组分可以有效地合成各种含肌酮的化合物。以烯烃或丙二烯作为2-碳组分，在七元环内设置多个立体中心。Tang教授还在研究这些新的[5+2]-环加成反应的机理和反应中间体。这些新的环加成方法为长期存在的挑战提供了解决方案，以开发有效的和立体选择性的合成条目进入单环或多环七元环。