Unexpected transformations: from 5-glyco-4-nitrocyclohexenes to bicyclic [3.3.1] oximes through isoxazoline N-oxides

Authors
Gil, MV Roman, E Serrano, JA
Citation
Mv. Gil et al., Unexpected transformations: from 5-glyco-4-nitrocyclohexenes to bicyclic [3.3.1] oximes through isoxazoline N-oxides, TETRAHEDR L, 41(17), 2000, pp. 3221-3224
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
17
Year of publication
2000
Pages
3221 - 3224
Database
ISI
SICI code
0040-4039(20000422)41:17<3221:UTF5TB>2.0.ZU;2-4
Abstract
Treatment of 5-glyco-4-nitrocyclohexenes with excess or equimolar sodium me thoxide gave deacetylated sodium nitronates which, on reaction with Ac2O/py , led to chiral isoxazoline N-oxides (cyclic nitronic esters). Depending on the configuration of their respective sugar side-chains, base-catalyzed de acetylation of these nitronate esters yielded either a bicyclic [3.3.1] oxi me or a deacetylated isoxazoline N-oxide. (C) 2000 Elsevier Science Ltd. Al l rights reserved.