Divergent Synthesis of Enantioenriched β-Functional Amines via Desymmetrization of <i>meso</i>-Aziridines with Isocyanides

Abstract

A highly enantioselective ring-opening desymmetrization of <i>meso</i>-aziridines with isocyanides was achieved in the presence of a chiral <i>N,N'</i>-dioxide/Mg(OTf)₂ complex. The in situ generated chiral 1,4-zwitterionic intermediates were successfully trapped by intramolecular oxygen- and carbon-based nucleophiles or exogenous H₂O and TMSN₃, enabling a collective synthesis of various chiral vicinal amino-oxazoles, spiroindolines, β-amino amides, and tetrazole derivative in moderate to high yields with excellent enantioselectivities.