Asymmetric Synthesis of Functionalized 2-Isoxazolines.

ABSTRACT: 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 α,β-unsaturated ketone intermediate which cyclized to the isoxazoline. The α,β-unsaturated double bond was successfully cleaved with RuCl₃·xH₂O catalysis en route to the isoxazoline skeleton bearing alcohol, aldehyde, and carboxylic acid functionalities.

SUBMITTER: Hamur B 

PROVIDER: S-EPMC11866192 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature