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

乙烯基环氧化物和乙烯基叠氮醚是广泛使用的合成中间体，但获取这些有价值结构的方法有很多。需要开发一种更简洁的合成方法，以获得复杂的和对映纯的乙烯基环氧化物和乙烯基叠氮醚。考虑到这个问题，我们的目标是通过环氧化物和烯烃之间的非常规分离，开发一种统一的乙烯基环氧化物和叠氮醚合成方法，并采用改性的茨威费尔烯烃将这两个片段连接起来。这两种组分都很容易从原料中获得，通过雅各布森动力学分辨，末端环氧化物和氮杂环很容易以对映体富集形式制备。我们计划在自动合成中使用这种化学，以评估方法的范围。

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.