N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines

Abstract

Transition metal-mediated N–O bond cleavage reactions of heterobicycloalkene-fused 3-methyl-2-isoxazolines were investigated. Optimal cleavage conditions were found with Raney nickel/AlCl3 mediation in aqueous methanol. The reaction provided a diverse collection of novel heterobicycle-fused β-hydroxyketones with good to excellent yields (66–95%) and without the need for chromatographic purification.

Keywords

• azabicycloalkene
• β-hydroxyketone
• 2-isoxazoline
• oxabicycloalkene
• Raney nickel