Phosphine-Catalyzed Atroposelective Formal [3+2] Cycloaddition Desymmetrization of N-Arylmaleimides

Herein, a new strategy for the enantioselective synthesis of axially chiral N-aryl succinimides was devised by [3 + 2] annulation of MBH carbonates and N-aryl maleimides under chiral phosphine. This desymmetrization process allows for quick construction of both two stereogenic carbon centers and a remote C-Ar-N atropisomeric chirality. A series of structurally diverse N-aryl succinimides were obtained with good to excellent yields, diastereoselectivities, and enantioselectivities. The process is mild, efficient, and scalable and features a broad substrate scope.

Automated summary

A new strategy for the enantioselective synthesis of axially chiral N-aryl succinimides was developed using [3 + 2] annulation of MBH carbonates and N-aryl maleimides under chiral phosphine. This process allows for the efficient construction of stereogenic carbon centers and remote C-Ar-N atropisomeric chirality. The method exhibits mild reaction conditions, high efficiency, scalability, and a broad substrate scope.