Nitro-Enabled Atroposelective Dynamic Kinetic Resolution of 2-Arylindoles by Phase-Transfer Catalysis

Abstract

This study presents the atroposelective alkylation of 2-arylindoles catalyzed by a substituted cinchonium salt as a phase-transfer catalyst. Under the optimized reaction conditions, various substrates are employed to yield products with high enantioselectivity. The presence of an ortho-nitro group at the aromatic ring is essential for high atroposelectivity, because it facilitates favorable interactions between the catalyst and substrate. The origin of the enantioselectivity reveals favorable π–π interactions for both enantiomers and unfavorable steric strains for undesired enantiomers.