Remote generation of N–N axial chirality through asymmetric hydrophosphinylation/hydroamination of maleimides

Abstract

Despite the significance of N–N axially chiral compounds in medicinal chemistry and asymmetric catalysis, there are limited reports on the asymmetric synthesis of N–N axially chiral compounds that also possess a phosphorus- or nitrogen-containing carbon stereogenic center. In this study, we developed organocatalytic hydrophosphinylation and hydroamination reactions of maleimides, enabling simultaneous creation of N–N axial chirality alongside a remote phosphorus or nitrogen-containing carbon chiral centre. These processes formed products in high yields with excellent enantioselectivities. The reported method represents an effective approach to construct structurally demanding chiral molecular scaffolds containing multiple chiral elements.