title: 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.
authors.affiliation: Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry and Biochemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada.
authors.forename: Jaipal R
authors.initials: JR
authors.lastname: Nagireddy
authors.affiliation: Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry and Biochemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada.
authors.forename: Geoffrey K
authors.initials: GK
authors.lastname: Tranmer
authors.affiliation: Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry and Biochemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada.
authors.forename: Emily
authors.initials: E
authors.lastname: Carlson
authors.affiliation: Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry and Biochemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada.
authors.forename: William
authors.initials: W
authors.lastname: Tam
keywords: 2-isoxazoline; Raney nickel; azabicycloalkene; oxabicycloalkene; β-hydroxyketone