Synthesis of Chiral Aziridine Alcohols via Parallel Kinetic Resolutions

We present a parallel kinetic resolution (PKR) of racemic 2 H -azirines via zinc-catalyzed direct nucleophilic additions to the C=N double bonds with 2-hydroxyacetophenones. Two sets of separable diastereomers of chiral aziridine alcohols bearing three adjacent stereocenters are prepared with high enantioselectivity. Diastereodivergent synthesis of four stereoisomers is realized by switching the absolute configurations of the chiral ligand. Control experiments and DFT calculations are carried out to shed light on the stereochemical models during the PKR progress.