A convenient and efficient ring-opening reaction of aziridines with acetylenes and synthesis of dihydropyrroles

In the presence of 'BuOK, reaction of acetylenes with N-Ts substituted aziridines derived from both cyclic and acyclic alkenes at room temperature gave rise to homopropargylamines in good to high yields and in high regioselectivity. Not only Ph- and Me3Si-substituted acetylenes but also acetylene itself was suitable reagents. Treatment of ring-opening products with I-2 and AgOAc in the presence of K2CO3 provided dihydropyrroles in high yields. One-pot synthesis of dihydropyrroles was also realized by the reaction of aziridines and phenylacetylene in the presence of NaH followed by the treatment with I-2 and AgOAc. (c) 2005 Elsevier Ltd. All rights reserved.