Direct Synthesis of Chiral 1,2,3,4-Tetrahydropyrrolo[1,2-<i>a</i>]pyrazines via a Catalytic Asymmetric Intramolecular Aza-Friedel–Crafts Reaction

Abstract

The direct asymmetric intramolecular aza-Friedel-Crafts reaction of N-aminoethylpyrroles with aldehydes catalyzed by a chiral phosphoric acid represents the first efficient method for the preparation of medicinally interesting chiral 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines with high yields and high enantioselectivities. This strategy has been shown to be quite general toward various aldehydes and pyrrole derivatives.