Construction of Cyclic Nitrones Enabled by Photodriven and Gold-Catalyzed 1,3-Azaprotio Transfer of Allenyloximes

A protocol was developed to construct five- to seven-membered cyclic nitrones through the gold-catalyzed 1,3-azaprotio transfer of allenyloximes under photoirradiation. The photoisomerization of oximes was suggested to convert the inert stereoisomer to a reactive one. This photodriven and gold-catalyzed ring formation could be further extended to the thermodynamically stable aryl ketoximes with an E-configuration, which previously displayed chemical inertness in the absence of light irradiation.

Automated summary

A protocol was developed for the construction of cyclic nitrones using gold-catalyzed 1,3-azaprotio transfer of allenyloximes under photoirradiation. The photoisomerization of oximes could convert the inert stereoisomer to a reactive one. This photodriven and gold-catalyzed ring formation could also be applied to thermodynamically stable aryl ketoximes with an E-configuration.