A mild cascade approach for the generation of 2-(α-hydroxyacyl)pyrroles under Ag(I) catalysis has been reported. This strategy involves a 5-exo-dig cyclization of insitu generated imines from 6-hydroxyhex-2-en-4-ynals and primary amines followed by oxidation. The reaction is very general for propargylic alcohols, tethers and primary amines. Efficient synthesis of core structures of pyrrole based bioactive natural products have also been achieved. Control experiments revealed the fact that, presence of excess oxygen and water may favor the competitive formation of the furans over the pyrroles. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim