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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 ?-hydroxyketones with good to excellent yields (66-95%) and without the need for chromatographic purification.

SUBMITTER: Nagireddy JR

PROVIDER: S-EPMC4168885 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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

Nagireddy Jaipal R JR Tranmer Geoffrey K GK Carlson Emily E Tam William W

Beilstein journal of organic chemistry 20140916

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. ...[more]

PMID: 25246978

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