Dedicated to Prof. H. Ila on the occasion of her 80th birthday.
A simple strategy for the synthesis of a variety of dihydropyrroles in good to excellent yields via a Lewis acid catalyzed, quaternary ammonium salt mediated SN2-type ring opening followed by cyclization of activated aziridines with alkynes in a domino fashion is described. The formation and the observed stereoselectivities of the products via an SN2-/double SN2-type ring-opening pathway are rationalized by mechanistic studies.
Key words
aziridines - alkynes - dihydropyrroles - S
N2-type ring opening - DROC