Photochemical Switchable Access to Spiro- γ -lactams and Spiro- γ -lactones from Olefins via a N to O Atom Swap

A chemodivergent platform for the synthesis of spirolactams and spirolactones has not been devised to date due to the inherent difference in the heteroatom (N vs O). Major challenges include finding a suitable N to O atom swap strategy and tactical reagent design. Herein, we describe a visible-light-mediated strategy that can install both spiro-γ-lactams and lactones onto olefins from suitable oxime esters via a merger with a N to O atom swap. This exchange is achieved by the venerated diazotization reaction, providing a rare example of its application to nonaromatic amines.