Catalytic Asymmetric [3+2] Annulation of Hantzsch Esters with Racemic N-Sulfonylaziridines

Hantzsch esters (HEs) served as two-carbon partners in a copper(I)-catalyzed enantioselective [3 + 2] annulation with racemic 2-(hetero)aryl-N-sulfonyl aziridines via kinetic resolution to provide pyrrolo[2,3-b]tetrahydropyridines containing multiple contiguous stereogenic centers including all-carbon quaternary centers in excellent yields and enantiopurities and moderate-to-excellent diastereoselectivities. Mainly dependent upon the structures of the aziridines, a competitive hydrogenolysis process with HEs as the hydrogen source was also observed in some cases.

Automated summary

In this study, Hantzsch esters (HEs) were used as two-carbon partners in a copper(I)-catalyzed enantioselective [3 + 2] annulation with racemic 2-(hetero)aryl-N-sulfonyl aziridines via kinetic resolution to provide pyrrolo[2,3-b]tetrahydropyridines containing multiple contiguous stereogenic centers. The reactions yielded products with excellent yields and enantiopurities, as well as moderate-to-excellent diastereoselectivities. Depending on the structures of the aziridines, a competitive hydrogenolysis process with HEs as the hydrogen source was also observed in some cases.