Stereoselective Cyclopropanation of Boron Dipyrromethene (BODIPY) Derivatives by an Organocascade Reaction

The synthesis of enantiopure chiral boron dipyrromethenes (BODIPYs) is importance due the intrinsic properties BODIPYs as fluorophores that could be used probes for molecular sensing. present study reports an asymmetric organocatalytic cascade reaction meso-chloromethyl BODIPY derivatives with α,β-unsaturated aldehydes catalyzed by a secondary amine. corresponding BODIPY-derived cyclopropanes were produced in isolated yields 66–98%, and diastereomeric ratios 3/2–>20/1, 92–99% ee major diastereomer. synthetic utility protocol was exemplified on set additional transformations optically pure compounds. In addition, explaining mechanism (DFT computations) photophysical characterization all enantioenriched products accomplished.