NHC-Catalyzed Kinetic Resolution for the Synthesis of Boron-Stereogenic BODIPYs

The
enantioselective synthesis of boron-stereogenic compounds
remains
a formidable challenge in modern synthetic chemistry due to the limited
availability of efficient catalytic strategies. Herein, we report
an N-heterocyclic carbene (NHC)-catalyzed kinetic resolution of 3-formyl
BODIPYs, which provides access to enantioenriched 3-formyl BODIPYs
and aryl 3-carboxylate BODIPYs in good to high yields with high enantioselectivities
(up to 96% ee). This method features a broad substrate scope, mild
reaction conditions, and exceptional functional group tolerance. Furthermore,
the resulting chiral BODIPYs exhibit promising circularly polarized
luminescence properties. This work represents the successful application
of NHC catalysis for constructing boron-stereogenic centers, expanding
the toolbox for asymmetric organocatalysis.