Diastereo- and Enantioselective Palladium-Catalyzed Dearomative [3+2] Cycloaddition of 3-Nitroindoles

Abstract

Diastereo- and enantioselective cycloaddition of 3-nitroindoles with vinyl aziridine was realized under Pd-catalysis using commercially available Walphos as the ligand, affording pyrroloindolines in high yields with high diastereo- and enantioselectivities. The reaction can be scaled up to a gram scale and the reaction products are easily converted to amino pyrroloindoline and other pyrroloindoline derivatives.

Keywords: [3+2] cycloaddition; asymmetric catalysis; dearomatization; nitroindoles; palladium.