LiAlH4‐Induced Selective Ring Rearrangement of 2‐(2‐Cyanoethyl)aziridines toward 2‐(Aminomethyl)pyrrolidines and 3‐Aminopiperidines as Eligible Heterocyclic Building Blocks

Abstract

2‐(2‐Cyanoethyl)aziridines and 2‐aryl‐3‐(2‐cyanoethyl)aziridines were deployed as substrates for an In(OTf)₃‐mediated regio‐ and stereoselective ring rearrangement upon treatment with LiAlH₄, affording a variety of novel 2‐(aminomethyl)pyrrolidines and 3‐aminopiperidines, respectively. Further synthetic elaboration of the obtained 3‐aminopiperidines resulted in the formation of a peculiar and unexplored conformationally constrained imidazolidinone and diketopiperazine scaffold.