Coupling of Lithiated Epoxides/Aziridines with Vinyl Boronic Esters and its Applications

锂化环氧化物/氮丙啶与乙烯基硼酸酯的偶联及其应用

• 批准号: 2737554
• 金额: --
• 依托单位: University of Bristol
• 依托单位国家: 英国
• 项目类别: Studentship
• 财政年份: 2019
• 资助国家: 英国
• 起止时间: 2019 至 无数据
• 项目状态: 已结题
• 来源: https://gtr.ukri.org/projects?ref=studentship-2737554
• 关键词: Coupling; Lithiated; Epoxides; Aziridines; Vinyl

Vinyl epoxides and vinyl aziridines are widely used synthetic intermediates however there are many methods to access these valuable structures. A more concise synthesis is required to be developed to access both complex and enantiopure vinyl epoxides and Vinyl aziridines. With this issue in mind we aim to develop a unified synthesis of vinyl epoxides and aziridines through the unconventional disconnection between the epoxide and the alkene and employ a modified Zweifel olefination to connect the two fragments. Both components are readily accessible from feedstock materials and terminal epoxides and aziridines are easily prepared in enantioenriched form through Jacobsen kinetic resolution. We plan to use this chemistry in automated synthesis, to assess the scope of the methodology.

乙烯基环氧化物和乙烯基氮丙啶是广泛使用的合成中间体，然而有许多方法来获得这些有价值的结构。需要开发一种更简洁的合成方法来获得复杂的和对映体纯的乙烯基环氧化物和乙烯基氮杂环丙烷。考虑到这个问题，我们的目标是开发一个统一的合成乙烯基环氧化物和氮杂环丙烷通过非常规的断开之间的环氧化物和烯烃，并采用一个修改的Zweifel烯化连接的两个片段。这两种组分都容易从原料中获得，并且末端环氧化物和氮杂环丙烷容易通过Jacobsen动力学拆分以对映体富集的形式制备。我们计划在自动合成中使用这种化学方法，以评估该方法的范围。