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

Authors
  • Nagireddy, Jaipal R
  • Tranmer, Geoffrey K
  • Carlson, Emily
  • Tam, William
Type
Published Article
Journal
Beilstein Journal of Organic Chemistry
Publisher
Beilstein-Institut
Publication Date
Jan 01, 2014
Volume
10
Pages
2200–2205
Identifiers
DOI: 10.3762/bjoc.10.227
PMID: 25246978
Source
Medline
Keywords
License
Unknown

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.

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