Enantioselective transformations and continuous-flow synthesis of fluorinated diazoalkanes

氟化重氮烷的对映选择性转化和连续流合成

• 批准号: 408033718
• 负责人: Professor Dr. Rene M. Koenigs
• 金额: --
• 依托单位: Institut für Organische Chemie (IOC)
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2018
• 资助国家: 德国
• 起止时间: 2017-12-31 至 2020-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/408033718?language=en
• 关键词: Enantioselective; transformations; continuous; flow; synthesis

Fluorinated diazo alkanes are a long established class of compounds, yet the synthetic applicability of these small and highly reactive molecules has only recently been investigated. Enantioselective transformations of these reagents and their synthesis in continuous-flow have so far been hardly addressed and allow novel applications for the synthesis of fluorinated molecues.The aim of this research project is to investigate these fluorinated diazoalkanes in enantioselective rearrangement reactions. This type of reaction is still one of the major challenges in asymmetric catalysis and has hardly been studied so far. Rearrangement reactions with fluorinated diazoalkanes provide novel access to valuable fluorinated, highly functionalized heterocycles and building blocks.In a second part, non-isolable fluorinated diazoalkanes will be investigated in continuous-flow. This way, these highly reactive diazo compounds can be safely made available for organic synthesis. Thus, new and unique transformations for organic synthesis can be investigated. This concept opens up efficient access to chemical space, which until now has been difficult to address synthetically.

氟化重氮烷烃是一类由来已久的化合物，但直到最近才对这些小而高活性分子的合成适用性进行了研究。迄今为止，这些试剂的对映选择性转化及其在连续流动中的合成几乎没有得到解决，并为氟化分子的合成提供了新的应用。本研究项目的目的是研究这些氟化重氮烷烃在对映选择性重排反应中的作用。这种类型的反应仍然是不对称催化的主要挑战之一，迄今为止几乎没有研究。与氟化重氮烷烃的重排反应为有价值的氟化、高官能化的杂环和构建块提供了新的途径。在第二部分，不可分离的氟化重氮烷烃将在连续流研究。这样，这些高活性的重氮化合物就可以安全地用于有机合成。因此，新的和独特的转化有机合成可以研究。这一概念开辟了通往化学空间的有效途径，到目前为止，化学空间很难通过人工合成来解决。

项目成果

Synthesis of Trifluoromethylated Tetrasubstituted Allenes via Palladium-Catalyzed Carbene Transfer Reaction.

• DOI: 10.1021/acs.orglett.0c02638
• 发表时间: 2020-08
• 期刊: Organic letters
• 影响因子: 5.2
• 作者: C. Pei;Zhen Yang;Rene M. Koenigs