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

J. Org. Chem.201883 (7), pp 3570–3581
DOI: 10.1021/acs.joc.7b03189
Publication Date (Web): March 2, 2018

AbstractA 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.