Dynamic kinetic resolution of beta-azido alcohols. An efficient route to chiral aziridines and beta-amino alcohols
Related Experiment Video
Updated: Oct 7, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
1Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-10691 Stockholm, Sweden.
Abstract:
Enzymatic resolution of beta-azido alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution. A variety of racemic beta-azido alcohols were efficiently transformed to the corresponding enantiomerically pure acetates (ee up to 99% and conversion up to 98%). The synthetic utility of this procedure has been illustrated by the practical synthesis of (S)-propanolol I and (R)-beta-azido-alpha-(4-methoxyphenyl)ethanol ((R)-1c), a direct precursor of denopamine II.
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Conversion of Alcohols to Alkyl Halides
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

