Asymmetric synthesis of acyclic N–N axially chiral indole compounds via catalytic N-acylation reaction

Abstract

Herein, we present a highly enantioselective synthesis of N-aminoindoles containing the N–N axis by chiral isothiourea (ITU) catalyzed asymmetric N-acylation of N-aminoindoles with carboxylic anhydrides, producing a series of N–N axially chiral indole derivatives with high yields and enantioselectivities under mild conditions. Notably, this reaction features a broad substrate scope, easy scalability, and facile derivatization of products. In addition, some of the enantiopure N-aminoindole products exhibited promising cytotoxicity activities against some cancer cell lines, highlighting the potential utility of this methodology.