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

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。

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.