Regio‐ and Enantioselective Synthesis of Succinimides Bearing All‐Carbon Quaternary Centers Using a Chiral Phenanthroline‐Palladium Catalyst.

The synthesis of chiral succinimides bearing all‐carbon quaternary stereocenters at the C3 position is important, but remains challenging. The present work demonstrates conjugate additions with catalysis by a chiral 1,10‐phenanthroline‐Pd complex (L1‐PdCl2) that exhibit complete regioselectivity with a high degree of enantioselectivity. These reactions afford chiral 3,3‐disubstituted succinimides having all‐carbon quaternary stereocenters with 40–99% ee. Importantly, chiral 3,3‐diaryl succinimides could also be obtained in 35–98% yields and 40–99% ee. Moreover, the present L1‐PdCl2‐catalyzed asymmetric conjugate addition could be performed on the gram scale and was also used to introduce such stereocenters into bioactive molecules. [ABSTRACT FROM AUTHOR]