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

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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.