Gold-Catalyzed Stereoselective Synthesis of Azacyclic Compounds

Significance

The authors report a metal-catalyzed stereoselective redox/[2+2+1] cycloaddition cascade sequence. From achiral commercially available starting materials, complex azacyclic compounds can be formed in a one-step protocol. The yields from this procedure are moderate to good and a variety of electron-rich alkenes can be employed. The authors also demonstrate that the reaction is tolerant of a wide array of substitution patterns on the phenyl moiety of the nitrobenzene starting material. Theoretical and experimental mechanistic investigations are performed.