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

Abstract

AbstractThe 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.