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.

Department of Analytical Chemistry Faculty of Science Palacký University Olomouc 17 listopadu 1192 12 77900 Olomouc Czech Republic

Department of Inorganic Chemistry Faculty of Science Palacký University Olomouc 17 listopadu 1192 12 77900 Olomouc Czech Republic

Department of Organic Chemistry Faculty of Science Palacký University Olomouc 17 listopadu 1192 12 77900 Olomouc Czech Republic

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