Palladium-Catalyzed Enantioselective Migratory Hydroamidocarbonylation of Amide-Linked Alkenes to Access Chiral α-Alkyl Succinimides.

Abstract

A Pd-catalyzed asymmetric isomerization-hydroamidocarbonylation of amide-containing alkenes was developed, affording a variety of chiral a-alkyl succinimides in moderate to good yields with high enantioselectivities. The key to success was introducing bulky 1-adamentyl P-substitution and 2,3,5,6-tetramethoxyphenyl group into the rigid P-chirogenic bisphosphine ligand to create stronger steric hinderance and deeper catalytic pocket. By this approach, regio- or stereo-convergent synthesis of enantiomeric succinimides from the mixture of olefin isomers was achieved.