Iminologous Epoxide Ring-Closure

Herein, we apply the principle of iminology to the well-established epoxide ring-closure reaction. The synthesis of tetrasubstituted, nitrile-tethered epoxides can be achieved via activation of iminologous diols followed by fragmentation. Mechanistic study reveals the transformation to be stereoretentive, which is consistent with the concerted nature of the epoxide ring-closure.