Stereoselective addition reactions with nitroso derivatives

与亚硝基衍生物的立体选择性加成反应

• 批准号: 157515232
• 负责人: Professor Dr. Armido Studer
• 金额: --
• 依托单位: Organisch-Chemisches Institut
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2009
• 资助国家: 德国
• 起止时间: 2008-12-31 至 2016-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/157515232?language=en
• 关键词: Stereoselective; addition; reactions; nitroso; derivatives

On the basis of very successful studies obtained in the first funding period novel stereoselective reactions with nitroso arenes will be established. The novel methods will offer new approaches to important substance classes. Three different stereoselective processes will be addressed. In the first subproject we plan reacting donor-acceptor-cyclopropanes with nitroso arenes in the presence of Lewis acids as catalysts to give enantiomerically pure isoxazolidines in a formal [2+3]-cycloaddition reaction. In addition we will investigate in the second funding period [2+2]-cycloadditions of nitrosoarenes with electron rich alkenes. Along these lines a novel method for the preparation of alpha-aminated lactones will be developed. Finally, the third subproject deals with the reaction of allylboronic acid esters with nitroso arenes for the synthesis of enantiomerically pure allyl alcohols.

在第一个资助期获得的非常成功的研究的基础上，将建立与亚硝基芳烃的新型立体选择性反应。新方法将为重要物质类别提供新方法。三个不同的立体选择性的过程将被解决。在第一个子项目中，我们计划在刘易斯酸催化下，使给体-受体-环丙烷与亚硝基芳烃进行[2+3]-环加成反应，得到对映体纯的异恶唑烷。此外，我们将在第二个资助期内研究亚硝基芳烃与富电子烯烃的[2+2]-环加成反应。沿着这些路线，将开发用于制备α-胺化内酯的新方法。最后，第三个子项目是烯丙基硼酸酯与亚硝基芳烃反应合成对映体纯的烯丙醇。

项目成果

An efficient approach to chiral allyloxyamines by stereospecific allylation of nitrosoarenes with chiral allylboronates.

• DOI: 10.1002/anie.201410188
• 发表时间: 2015-03
• 期刊: Angewandte Chemie
• 作者: Yuanming Li;Shyamal Chakrabarty;A. Studer

Copper-Catalyzed Enantioselective [2+2] Cycloadditions of 2-Nitrosopyridine with Ketenes

• DOI: 10.1002/adsc.201000153
• 发表时间: 2010-04
• 期刊: Advanced Synthesis & Catalysis
• 影响因子: 5.4
• 作者: I. Chatterjee;C. Jana;M. Steinmetz;S. Grimme;A. Studer