What question did this study set out to answer?

The research aims to synthesize chiral aziridine alcohols using parallel kinetic resolution methods.

April 19, 2026ACS Catalysis0 citations

Synthesis of Chiral Aziridine Alcohols via Parallel Kinetic Resolutions

XWXiao-Ge WangZhengzhou University XKXiang-Tao KongAnyang Normal University HXHua XieDalian Institute of Chemical Physics

Key Points

The research aims to synthesize chiral aziridine alcohols using parallel kinetic resolution methods.
Conduct parallel kinetic resolution of racemic 2H-azirines.
Utilize zinc-catalyzed direct nucleophilic additions to C=N double bonds.
Prepare two separable diastereomers of chiral aziridine alcohols.
Perform control experiments and DFT calculations to analyze stereochemical models.
High enantioselectivity achieved in synthesizing chiral aziridine alcohols.
Successfully realized diastereodivergence to produce four stereoisomers.
Stereochemical models were elucidated through DFT calculations.

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.

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