Synthesis and applications of methyleneaziridines

Abstract

This review surveys the structural characterization, synthetic methods, chemical transformations and mechanisms of methyleneaziridines, especially the advances achieved over the past decade.

Solvent-Controlled Regioselective Reaction of 2-Methyleneaziridines with Acrylic/Propargylic Acids: Synthesis of Carboxylate Aziridine/Acetone Esters

“…The electrophilicity of carbon atoms on MAs ring inspired us to develop a convenient and efficient esterification in which carboxylic acids would be utilized as nucleophiles without preactivation (Scheme b). Because of our continuing interest in MAs, herein, we report a facile regioselective esterification of carboxylic acids with MAs under mild conditions without any non-green carboxyl activation strategy. This process efficiently provides two types of carboxylate esters in good yields via a solvent-controlled switch of selectivity between the sp 2 and sp 3 carbon nucleophilic reaction to MAs.…”