Pd(II)/N,N′-Disulfonyl bisimidazoline-catalyzed asymmetric arylation of isoquinoline-1,3,4-trione-derived ketimines

Abstract

A palladium/chiral N,N′-disulfonyl bisimidazoline (Bim)-catalyzed asymmetric addition of arylboronic acids to isoquinoline-1,3,4-trione-derived ketimines is reported, leading to the generation of a series of functionalized isoquinoline-1,3(2H,4H)-diones bearing one quaternary carbon-amino functionality in good to excellent yields with ≥95% ee in most cases. The reaction has remarkable compatibility with both substrate scopes, providing a highly enantioselective entry to chiral heterocyclic α-tertiary amines.

Keywords

• Pd(II)-Catalysis
• Asymmetric addition
• Bisimidazoline ligand
• α-Tertiary amines
• Enantioselectivity