Lewis Acid-Catalyzed Diastereoselective Synthesis of Multisubstituted N-Acylaziridine-2-carboxamides from 2 H-Azirines via Joullié-Ugi Three-Component Reaction

Anikó Angyal, András Demjén, Edit Wéber, Anita K. Kovács, János Wölfling, László G. Puskás, and Iván Kanizsai

A ZnCl2-catalyzed diastereoselective Joullié-Ugi three-component reaction from 2 H-azirines, isocyanides, and carboxylic acids was established. The protocol allows the preparation of highly and diversely functionalized N-acylaziridine-2-carboxamide derivatives in up to 82% isolated yields. Moreover, the applicability of N-acylaziridines is demonstrated through a variety of transformations.