Highly Regioselective and Chemoselective [3 + 3] Annulation of Enaminones with ortho-Fluoronitrobenzenenes: Divergent Synthesis of Aposafranones and Their N-Oxides.

A base-promoted unprecedented strategy for the regioselective and chemoselective divergent synthesis of highly functionalized aposafranones and their N-oxides has been developed from the [3 + 3] annulation of enaminones with o-fluoronitrobenzenenes. This novel synthetic strategy offers an alternative method for the construction of aposafranones and their N-oxides are meaningful in the fields of both biology and organic synthesis. The established protocol explores the annulation scope of enaminones, and it expands the application of nitro-based cyclization.