Asymmetric one-pot sequential Friedel–Crafts-type alkylation and α-oxyamination catalyzed by a peptide and an enzyme

Abstract

In the presence of a peptide catalyst and the oxidative enzyme laccase, a one-pot sequential reaction including a Friedel–Crafts-type alkylation of α,β-unsaturated aldehydes followed by an α-oxyamination was realized. The reaction in aqueous solvent to promote the enzymatic oxidation, and the use of a peptide catalyst compatible with such conditions, were essential. The present sequential reaction afforded oxygen-functionalized indole or pyrrole derivatives in a highly enantioselective manner.