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长期建立的化合物，但是这些小型反应性分子的合成适用性直到最近才被研究。到目前为止，这些试剂及其在连续流中的合成的对映选择性转换几乎没有得到解决，并允许新颖的应用氟化分子的合成。该研究项目的目的是研究这些在对甲壳度的重排反应中这些氟化的重生反应。这种反应仍然是不对称催化的主要挑战之一，到目前为止几乎没有研究。与氟化重氮谷烷的重排反应为有价值的氟化，高度功能化的杂环和构建块提供了新的访问。在第二部分中，将在连续流中研究不可固定的氟化重氮烷烃。这样，这些高反应性的重氮化合物可以安全地用于有机合成。因此，可以研究有机合成的新的独特转换。这个概念可以有效地进入化学空间，到目前为止，这很难合成。

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