Calcium-Catalyzed Stereoselective Tandem [4+2] and [3+2] Annulation Reaction for the Synthesis of Dihydropyrrolo[1,2-<i>a</i>]quinolines

Abstract

Calcium-catalyzed highly facile one-pot, A4 annulation of aldehyde, amine, alkene, and alkyne to form fused 4,5-dihydropyrrolo[1,2-a]quinolines with exclusive syn diastereoselectivity is reported. This selectivity arises from an inverse electron demand [4+2] aza-Diels–Alder cycloaddition, and the adduct further undergoes a formal [3+2] cyclization with activated alkynes. This diversity-oriented protocol is highly general and furnishes the dihydropyrrolo[1,2-a]quinoline derivatives with a broad substrate scope in good to excellent yields.