Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction

Citation
P. Aschwanden et al., Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction, ORG LETT, 2(15), 2000, pp. 2331-2333
Citations number
31
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
15
Year of publication
2000
Pages
2331 - 2333
Database
ISI
SICI code
1523-7060(20000727)2:15<2331:SO2FPN>2.0.ZU;2-R
Abstract
[GRAPHICS] A novel cyclization reaction of propargylic N-hydroxylamines to 2,3,5-trisu bstituted 2,3-dihydroisoxazoles in the presence of catalytic amounts (10 mo l %) of Znl(2) and DMAP is reported. The methodology provides a mild new ap proach to this useful class of substituted heterocycles that complements ex tant methods. The unique reactivity of the propargylic N-hydroxylamine subs trates in the presence of Zn(II) and DMAP may have additional applications in other, related alkyne cyclization reactions.