Synthesis of Chiral Aziridine Alcohols via Parallel Kinetic Resolutions
Abstract
Abstract We present a parallel kinetic resolution (PKR) of racemic 2H-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.
Fields of Study & Subjects
Synthesis and Catalytic Reactions
Asymmetric Hydrogenation and Catalysis
Asymmetric Synthesis and Catalysis
Publication details
- Journal / source
- ACS Catalysis
- Publisher
- American Chemical Society (ACS)
- Volume
- 16
- Issue
- 9
- Pages
- 8692–8701
- Publication date
- 16 April 2026
- Language
- EN