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

An-Qi Miao,¹ Yu-Xin Wang,¹ Lin-Lin Xu,¹ Wen-Juan Hao,* Shu-Jiang Tu, Jin-Peng Zhang,* Bo Jiang*

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.

Green Synth. Catal. 2024, 5, 165-169; DOI: 10.1016/j.gresc.2023.07.001