Axially chiral dimethylaminobenzimidazoles and their preliminary evaluation as acyl-transfer reagents

Abstract

The synthesis of axially chiral benzimidazoles with a peri-substituted naphthalene and a dimethylamino group at positions 1 and 2, respectively, was developed. We evaluated these compounds in the desymmetrization reaction of cis-tetrahydrophthalic anhydride with benzyl alcohol, as the nucleophilic sp² imidazole nitrogen atom is able to catalyze the acyl-transfer reaction. The prepared benzimidazoles demonstrated catalytic activity and showed that their axial chirality impacts stereoselectivity.