REVERSAL OF REGIOCHEMISTRY IN THE SYNTHESIS OF ISOXAZOLES BY NITRILE OXIDE CYCLOADDITIONS

Authors
EASTON CJ HUGHES CM TIEKINK ERT LUBIN CE SAVAGE GP SIMPSON GW
Citation
Cj. Easton et al., REVERSAL OF REGIOCHEMISTRY IN THE SYNTHESIS OF ISOXAZOLES BY NITRILE OXIDE CYCLOADDITIONS, Tetrahedron letters, 35(21), 1994, pp. 3589-3592
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
21
Year of publication
1994
Pages
3589 - 3592
Database
ISI
SICI code
0040-4039(1994)35:21<3589:RORITS>2.0.ZU;2-S
Abstract
The isoxazolines 2a, 2b and 8 obtained from nitrile oxide cycloadditio ns to cyclohex-2-enone 1a and its analogues 1b and 7 reacted with nick el peroxide to give the isoxazoles 3a, 3b and 9. In contrast, the corr esponding 2-bromocyclohex-2-enones 4a, 4b and 10, prepared by brominat ion of the corresponding alkenes la, Ib and 7, underwent nitrile oxide cycloadditions to afford the regioisomeric isoxazoles 6a, 6b and 12, respectively.