Published January 1, 2025
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Asymmetric Synthesis of Functionalized 2-Isoxazolines
Creators
- 1. Gebze Tech Univ, Coll Sci, Dept Chem, TR-41400 Gebze, Kocaeli, Turkiye
- 2. Drexel Univ, Dept Chem, Philadelphia, PA 19104 USA
Description
The asymmetric synthesis of the isoxazoline skeleton was achieved by the oxidation of hydroxylaminoalkyl furan prepared from simple starting materials: 2-methylfuran and (S)-epichlorohydrin. The synthesis features an NBS-mediated oxidation of hydroxylaminoalkyl furan to give an alpha,beta-unsaturated ketone intermediate which cyclized to the isoxazoline. The alpha,beta-unsaturated double bond was successfully cleaved with RuCl3xH2O catalysis en route to the isoxazoline skeleton bearing alcohol, aldehyde, and carboxylic acid functionalities.
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