Ring-opening of azetidiniums by nucleophiles. Synthesis of polysubstituted linear amines

Abstract

This microreview focuses on the nucleophilic ring-opening of azetidiniums presenting various substitution patterns at C2, C3, and C4. In most cases, the nucleophilic ring-opening occurred in a stereoselective and regioselective fashion producing functionalized linear amines. Experimental selectivities associated with Density Functional Theory (DFT) calculations have allowed a better understanding of the parameters governing the regioselectivities.

Keywords: SN2; amine; azetidine; azetidinium; diastereoselectivity; nucleophilic ring-opening; regioselectivity.