Enantioselective Reaction of 2H-Azirines

Abstract

2H-Azirines are useful precursors for the synthesis of a variety of chiral aziridine and amine derivatives with a range of biological activities. Owing to the ring strain and the presence of a C=N double bond, 2H-azirines are more reactive than other types of ketimine, and undergo a range of enantioselective reactions, including reduction and Diels-Alder reactions, as well as nucleophilic addition to the C=N double bond. Therefore, the enantioselective reactions of 2H-azirines has become a hot topic, in particular within the last few years. In this Minireview, we focus on the enantioselective reactions of 2H-azirines by using catalytic or stoichiometric amounts of chiral additives, the reaction mechanisms, and the applications of these reactions of 2H-azirines and related compounds in organic synthesis.

Keywords: aziridines; azo compounds; enantioselectivity; kinetic resolution; synthetic methods.