Atroposelective Haloamidation of Indoles with Amino Acid Derivatives and Hypohalides.

Abstract

An atroposelective coupling of indoles with chiral amino acid-based sulfonamides mediated by hypohalides is described. A series of 2-amido-3-haloindoles with a C-N chiral axis are delivered using this strategy. The C3 halogen atoms can facilitate further transformation. Various functionalities, such as carbonyl, phosphine, aryl, and alkenyl groups, can be introduced into the C3 position of indoles. These structurally diverse and axially chiral indole derivatives can find further synthetic utilities. It can be exemplified with an axially chiral phosphine, which serves as a ligand in Pd-catalyzed cross couplings.